diff --git a/build.sbt b/build.sbt
index 7284171c..ad809ec5 100644
--- a/build.sbt
+++ b/build.sbt
@@ -148,7 +148,8 @@ val store = project.in(file("modules/store")).
       Dependencies.fs2 ++
       Dependencies.databases ++
       Dependencies.flyway ++
-      Dependencies.loggingApi
+      Dependencies.loggingApi ++
+      Dependencies.emil
   ).dependsOn(common)
 
 val text = project.in(file("modules/text")).
@@ -225,7 +226,8 @@ val backend = project.in(file("modules/backend")).
       Dependencies.loggingApi ++
       Dependencies.fs2 ++
       Dependencies.bcrypt ++
-      Dependencies.http4sClient
+      Dependencies.http4sClient ++
+      Dependencies.emil
   ).dependsOn(store)
 
 val webapp = project.in(file("modules/webapp")).
diff --git a/modules/backend/src/main/scala/docspell/backend/BackendApp.scala b/modules/backend/src/main/scala/docspell/backend/BackendApp.scala
index 05ed9347..59982761 100644
--- a/modules/backend/src/main/scala/docspell/backend/BackendApp.scala
+++ b/modules/backend/src/main/scala/docspell/backend/BackendApp.scala
@@ -9,6 +9,7 @@ import docspell.store.ops.ONode
 import docspell.store.queue.JobQueue
 
 import scala.concurrent.ExecutionContext
+import emil.javamail.JavaMailEmil
 
 trait BackendApp[F[_]] {
 
@@ -23,14 +24,16 @@ trait BackendApp[F[_]] {
   def node: ONode[F]
   def job: OJob[F]
   def item: OItem[F]
+  def mail: OMail[F]
 }
 
 object BackendApp {
 
-  def create[F[_]: ConcurrentEffect](
+  def create[F[_]: ConcurrentEffect: ContextShift](
       cfg: Config,
       store: Store[F],
-      httpClientEc: ExecutionContext
+    httpClientEc: ExecutionContext,
+    blocker: Blocker
   ): Resource[F, BackendApp[F]] =
     for {
       queue      <- JobQueue(store)
@@ -45,6 +48,7 @@ object BackendApp {
       nodeImpl   <- ONode(store)
       jobImpl    <- OJob(store, httpClientEc)
       itemImpl   <- OItem(store)
+      mailImpl   <- OMail(store, JavaMailEmil(blocker))
     } yield new BackendApp[F] {
       val login: Login[F]            = loginImpl
       val signup: OSignup[F]         = signupImpl
@@ -57,6 +61,7 @@ object BackendApp {
       val node                       = nodeImpl
       val job                        = jobImpl
       val item                       = itemImpl
+      val mail                       = mailImpl
     }
 
   def apply[F[_]: ConcurrentEffect: ContextShift](
@@ -67,6 +72,6 @@ object BackendApp {
   ): Resource[F, BackendApp[F]] =
     for {
       store   <- Store.create(cfg.jdbc, connectEC, blocker)
-      backend <- create(cfg, store, httpClientEc)
+      backend <- create(cfg, store, httpClientEc, blocker)
     } yield backend
 }
diff --git a/modules/backend/src/main/scala/docspell/backend/ops/OMail.scala b/modules/backend/src/main/scala/docspell/backend/ops/OMail.scala
new file mode 100644
index 00000000..5fad31bd
--- /dev/null
+++ b/modules/backend/src/main/scala/docspell/backend/ops/OMail.scala
@@ -0,0 +1,215 @@
+package docspell.backend.ops
+
+import fs2.Stream
+import cats.effect._
+import cats.implicits._
+import cats.data.OptionT
+import emil._
+import emil.javamail.syntax._
+import bitpeace.{FileMeta, RangeDef}
+
+import docspell.common._
+import docspell.store._
+import docspell.store.records._
+import docspell.store.queries.QMails
+import OMail.{ItemMail, Sent, SmtpSettings}
+
+trait OMail[F[_]] {
+
+  def getSettings(accId: AccountId, nameQ: Option[String]): F[Vector[RUserEmail]]
+
+  def findSettings(accId: AccountId, name: Ident): OptionT[F, RUserEmail]
+
+  def createSettings(accId: AccountId, data: SmtpSettings): F[AddResult]
+
+  def updateSettings(accId: AccountId, name: Ident, data: OMail.SmtpSettings): F[Int]
+
+  def deleteSettings(accId: AccountId, name: Ident): F[Int]
+
+  def sendMail(accId: AccountId, name: Ident, m: ItemMail): F[SendResult]
+
+  def getSentMailsForItem(accId: AccountId, itemId: Ident): F[Vector[Sent]]
+
+  def getSentMail(accId: AccountId, mailId: Ident): OptionT[F, Sent]
+
+  def deleteSentMail(accId: AccountId, mailId: Ident): F[Int]
+}
+
+object OMail {
+
+  case class Sent(
+      id: Ident,
+      senderLogin: Ident,
+      connectionName: Ident,
+      recipients: List[MailAddress],
+      subject: String,
+      body: String,
+      created: Timestamp
+  )
+
+  object Sent {
+
+    def create(r: RSentMail, login: Ident): Sent =
+      Sent(r.id, login, r.connName, r.recipients, r.subject, r.body, r.created)
+  }
+
+  case class ItemMail(
+      item: Ident,
+      subject: String,
+      recipients: List[MailAddress],
+      body: String,
+      attach: AttachSelection
+  )
+
+  sealed trait AttachSelection {
+    def filter(v: Vector[(RAttachment, FileMeta)]): Vector[(RAttachment, FileMeta)]
+  }
+  object AttachSelection {
+    case object All extends AttachSelection {
+      def filter(v: Vector[(RAttachment, FileMeta)]): Vector[(RAttachment, FileMeta)] = v
+    }
+    case class Selected(ids: List[Ident]) extends AttachSelection {
+      def filter(v: Vector[(RAttachment, FileMeta)]): Vector[(RAttachment, FileMeta)] = {
+        val set = ids.toSet
+        v.filter(set contains _._1.id)
+      }
+    }
+  }
+
+  case class SmtpSettings(
+      name: Ident,
+      smtpHost: String,
+      smtpPort: Option[Int],
+      smtpUser: Option[String],
+      smtpPassword: Option[Password],
+      smtpSsl: SSLType,
+      smtpCertCheck: Boolean,
+      mailFrom: MailAddress,
+      mailReplyTo: Option[MailAddress]
+  ) {
+
+    def toRecord(accId: AccountId) =
+      RUserEmail.fromAccount(
+        accId,
+        name,
+        smtpHost,
+        smtpPort,
+        smtpUser,
+        smtpPassword,
+        smtpSsl,
+        smtpCertCheck,
+        mailFrom,
+        mailReplyTo
+      )
+  }
+
+  def apply[F[_]: Effect](store: Store[F], emil: Emil[F]): Resource[F, OMail[F]] =
+    Resource.pure(new OMail[F] {
+      def getSettings(accId: AccountId, nameQ: Option[String]): F[Vector[RUserEmail]] =
+        store.transact(RUserEmail.findByAccount(accId, nameQ))
+
+      def findSettings(accId: AccountId, name: Ident): OptionT[F, RUserEmail] =
+        OptionT(store.transact(RUserEmail.getByName(accId, name)))
+
+      def createSettings(accId: AccountId, s: SmtpSettings): F[AddResult] =
+        (for {
+          ru <- OptionT(store.transact(s.toRecord(accId).value))
+          ins    = RUserEmail.insert(ru)
+          exists = RUserEmail.exists(ru.uid, ru.name)
+          res <- OptionT.liftF(store.add(ins, exists))
+        } yield res).getOrElse(AddResult.Failure(new Exception("User not found")))
+
+      def updateSettings(accId: AccountId, name: Ident, data: SmtpSettings): F[Int] = {
+        val op = for {
+          um <- OptionT(RUserEmail.getByName(accId, name))
+          ru <- data.toRecord(accId)
+          n  <- OptionT.liftF(RUserEmail.update(um.id, ru))
+        } yield n
+
+        store.transact(op.value).map(_.getOrElse(0))
+      }
+
+      def deleteSettings(accId: AccountId, name: Ident): F[Int] =
+        store.transact(RUserEmail.delete(accId, name))
+
+      def sendMail(accId: AccountId, name: Ident, m: ItemMail): F[SendResult] = {
+
+        val getSettings: OptionT[F, RUserEmail] =
+          OptionT(store.transact(RUserEmail.getByName(accId, name)))
+
+        def createMail(sett: RUserEmail): OptionT[F, Mail[F]] = {
+          import _root_.emil.builder._
+
+          for {
+            _ <- OptionT.liftF(store.transact(RItem.existsById(m.item))).filter(identity)
+            ras <- OptionT.liftF(
+              store.transact(RAttachment.findByItemAndCollectiveWithMeta(m.item, accId.collective))
+            )
+          } yield {
+            val addAttach = m.attach.filter(ras).map { a =>
+              Attach[F](Stream.emit(a._2).through(store.bitpeace.fetchData2(RangeDef.all)))
+                .withFilename(a._1.name)
+                .withLength(a._2.length)
+                .withMimeType(_root_.emil.MimeType.parse(a._2.mimetype.asString).toOption)
+            }
+            val fields: Seq[Trans[F]] = Seq(
+              From(sett.mailFrom),
+              Tos(m.recipients),
+              Subject(m.subject),
+              TextBody[F](m.body)
+            )
+
+            MailBuilder.fromSeq[F](fields).addAll(addAttach).build
+          }
+        }
+
+        def sendMail(cfg: MailConfig, mail: Mail[F]): F[Either[SendResult, String]] =
+          emil(cfg).send(mail).map(_.head).attempt.map(_.left.map(SendResult.SendFailure))
+
+        def storeMail(msgId: String, cfg: RUserEmail): F[Either[SendResult, Ident]] = {
+          val save = for {
+            data <- RSentMail.forItem(
+              m.item,
+              accId,
+              msgId,
+              cfg.mailFrom,
+              name,
+              m.subject,
+              m.recipients,
+              m.body
+            )
+            _ <- OptionT.liftF(RSentMail.insert(data._1))
+            _ <- OptionT.liftF(RSentMailItem.insert(data._2))
+          } yield data._1.id
+
+          store.transact(save.value).attempt.map {
+            case Right(Some(id)) => Right(id)
+            case Right(None) =>
+              Left(SendResult.StoreFailure(new Exception(s"Could not find user to save mail.")))
+            case Left(ex) => Left(SendResult.StoreFailure(ex))
+          }
+        }
+
+        (for {
+          mailCfg <- getSettings
+          mail    <- createMail(mailCfg)
+          mid     <- OptionT.liftF(sendMail(mailCfg.toMailConfig, mail))
+          res     <- mid.traverse(id => OptionT.liftF(storeMail(id, mailCfg)))
+          conv = res.fold(identity, _.fold(identity, id => SendResult.Success(id)))
+        } yield conv).getOrElse(SendResult.NotFound)
+      }
+
+      def getSentMailsForItem(accId: AccountId, itemId: Ident): F[Vector[Sent]] =
+        store
+          .transact(QMails.findMails(accId.collective, itemId))
+          .map(_.map(t => Sent.create(t._1, t._2)))
+
+      def getSentMail(accId: AccountId, mailId: Ident): OptionT[F, Sent] =
+        OptionT(store.transact(QMails.findMail(accId.collective, mailId))).map(t =>
+          Sent.create(t._1, t._2)
+        )
+
+      def deleteSentMail(accId: AccountId, mailId: Ident): F[Int] =
+        store.transact(QMails.delete(accId.collective, mailId))
+    })
+}
diff --git a/modules/backend/src/main/scala/docspell/backend/ops/SendResult.scala b/modules/backend/src/main/scala/docspell/backend/ops/SendResult.scala
new file mode 100644
index 00000000..f64f48f6
--- /dev/null
+++ b/modules/backend/src/main/scala/docspell/backend/ops/SendResult.scala
@@ -0,0 +1,26 @@
+package docspell.backend.ops
+
+import docspell.common._
+
+sealed trait SendResult
+
+object SendResult {
+
+  /** Mail was successfully sent and stored to db.
+    */
+  case class Success(id: Ident) extends SendResult
+
+  /** There was a failure sending the mail. The mail is then not saved
+    * to db.
+    */
+  case class SendFailure(ex: Throwable) extends SendResult
+
+  /** The mail was successfully sent, but storing to db failed.
+    */
+  case class StoreFailure(ex: Throwable) extends SendResult
+
+  /** Something could not be found required for sending (mail configs,
+    * items etc).
+    */
+  case object NotFound extends SendResult
+}
diff --git a/modules/common/src/main/scala/docspell/common/Ident.scala b/modules/common/src/main/scala/docspell/common/Ident.scala
index 199bd225..6314dffc 100644
--- a/modules/common/src/main/scala/docspell/common/Ident.scala
+++ b/modules/common/src/main/scala/docspell/common/Ident.scala
@@ -15,7 +15,7 @@ object Ident {
   implicit val identEq: Eq[Ident] =
     Eq.by(_.id)
 
-  val chars: Set[Char] = (('A' to 'Z') ++ ('a' to 'z') ++ ('0' to '9') ++ "-_").toSet
+  val chars: Set[Char] = (('A' to 'Z') ++ ('a' to 'z') ++ ('0' to '9') ++ "-_.").toSet
 
   def randomUUID[F[_]: Sync]: F[Ident] =
     Sync[F].delay(unsafe(UUID.randomUUID.toString))
@@ -32,7 +32,7 @@ object Ident {
 
   def fromString(s: String): Either[String, Ident] =
     if (s.forall(chars.contains)) Right(new Ident(s))
-    else Left(s"Invalid identifier: $s. Allowed chars: ${chars.mkString}")
+    else Left(s"Invalid identifier: '$s'. Allowed chars: ${chars.toList.sorted.mkString}")
 
   def fromBytes(bytes: ByteVector): Ident =
     unsafe(bytes.toBase58)
diff --git a/modules/restapi/src/main/resources/docspell-openapi.yml b/modules/restapi/src/main/resources/docspell-openapi.yml
index 88eba465..2e9a69e3 100644
--- a/modules/restapi/src/main/resources/docspell-openapi.yml
+++ b/modules/restapi/src/main/resources/docspell-openapi.yml
@@ -125,6 +125,8 @@ paths:
 
         The result shows all items that contains a file with the given
         checksum.
+      security:
+        - authTokenHeader: []
       parameters:
         - $ref: "#/components/parameters/checksum"
       responses:
@@ -159,6 +161,8 @@ paths:
         * application/pdf
 
         Support for more types might be added.
+      security:
+        - authTokenHeader: []
       requestBody:
         content:
           multipart/form-data:
@@ -1188,6 +1192,8 @@ paths:
         Get the current state of the job qeue. The job qeue contains
         all processing tasks and other long-running operations. All
         users/collectives share processing resources.
+      security:
+        - authTokenHeader: []
       responses:
         200:
           description: Ok
@@ -1203,6 +1209,8 @@ paths:
         Tries to cancel a job and remove it from the queue. If the job
         is running, a cancel request is send to the corresponding joex
         instance. Otherwise the job is removed from the queue.
+      security:
+        - authTokenHeader: []
       parameters:
         - $ref: "#/components/parameters/id"
       responses:
@@ -1212,8 +1220,291 @@ paths:
             application/json:
               schema:
                 $ref: "#/components/schemas/BasicResult"
+  /sec/email/settings:
+    get:
+      tags: [ E-Mail ]
+      summary: List email settings for current user.
+      description: |
+        List all available e-mail settings for the current user.
+        E-Mail settings specify smtp connections that can be used to
+        sent e-mails.
+
+        Multiple e-mail settings can be specified, they are
+        distinguished by their `name`. The query `q` parameter does a
+        simple substring search in the connection name.
+      security:
+        - authTokenHeader: []
+      parameters:
+        - $ref: "#/components/parameters/q"
+      responses:
+        200:
+          description: Ok
+          content:
+            application/json:
+              schema:
+                $ref: "#/components/schemas/EmailSettingsList"
+    post:
+      tags: [ E-Mail ]
+      summary: Create new email settings
+      description: |
+        Create new e-mail settings.
+      security:
+        - authTokenHeader: []
+      requestBody:
+        content:
+          application/json:
+            schema:
+              $ref: "#/components/schemas/EmailSettings"
+      responses:
+        200:
+          description: Ok
+          content:
+            application/json:
+              schema:
+                $ref: "#/components/schemas/BasicResult"
+  /sec/email/settings/{name}:
+    parameters:
+      - $ref: "#/components/parameters/name"
+    get:
+      tags: [ E-Mail ]
+      summary: Return specific email settings by name.
+      description: |
+        Return the stored e-mail settings for the given connection
+        name.
+      security:
+        - authTokenHeader: []
+      responses:
+        200:
+          description: Ok
+          content:
+            application/json:
+              schema:
+                $ref: "#/components/schemas/EmailSettings"
+    put:
+      tags: [ E-Mail ]
+      summary: Change specific email settings.
+      description: |
+        Changes all settings for the connection with the given `name`.
+      security:
+        - authTokenHeader: []
+      requestBody:
+        content:
+          application/json:
+            schema:
+              $ref: "#/components/schemas/EmailSettings"
+      responses:
+        200:
+          description: Ok
+          content:
+            application/json:
+              schema:
+                $ref: "#/components/schemas/BasicResult"
+    delete:
+      tags: [ E-Mail ]
+      summary: Delete e-mail settings.
+      description: |
+        Deletes the e-mail settings with the specified `name`.
+      security:
+        - authTokenHeader: []
+      responses:
+        200:
+          description: Ok
+          content:
+            application/json:
+              schema:
+                $ref: "#/components/schemas/BasicResult"
+
+  /sec/email/send/{name}/{id}:
+    post:
+      tags: [ E-Mail ]
+      summary: Send an email.
+      description: |
+        Sends an email as specified in the body of the request.
+
+        The item's attachment are added to the mail if requested.
+      security:
+        - authTokenHeader: []
+      parameters:
+        - $ref: "#/components/parameters/name"
+        - $ref: "#/components/parameters/id"
+      requestBody:
+        content:
+          application/json:
+            schema:
+              $ref: "#/components/schemas/SimpleMail"
+      responses:
+        200:
+          description: Ok
+          content:
+            application/json:
+              schema:
+                $ref: "#/components/schemas/BasicResult"
+  /sec/email/sent/item/{id}:
+    get:
+      tags: [ E-Mail ]
+      summary: Get sent mail related to an item
+      description: |
+        Return all mails that have been sent related to the item with
+        id `id`.
+      security:
+        - authTokenHeader: []
+      parameters:
+        - $ref: "#/components/parameters/id"
+      responses:
+        200:
+          description: Ok
+          content:
+            application/json:
+              schema:
+                $ref: "#/components/schemas/SentMails"
+  /sec/email/sent/mail/{mailId}:
+    parameters:
+      - $ref: "#/components/parameters/mailId"
+    get:
+      tags: [ E-Mail ]
+      summary: Get sent single mail related to an item
+      description: |
+        Return one mail with the given id.
+      security:
+        - authTokenHeader: []
+      responses:
+        200:
+          description: Ok
+          content:
+            application/json:
+              schema:
+                $ref: "#/components/schemas/SentMail"
+    delete:
+      tags: [ E-Mail ]
+      summary: Delete a sent mail.
+      description: |
+        Delete a sent mail.
+      security:
+        - authTokenHeader: []
+      responses:
+        200:
+          description: Ok
+          content:
+            application/json:
+              schema:
+                $ref: "#/components/schemas/BasicResult"
+
 components:
   schemas:
+    SentMails:
+      description: |
+        A list of sent mails.
+      required:
+        - items
+      properties:
+        items:
+          type: array
+          items:
+            $ref: "#/components/schemas/SentMail"
+    SentMail:
+      description: |
+        A mail that has been sent previously related to an item.
+      required:
+        - id
+        - sender
+        - connection
+        - recipients
+        - subject
+        - body
+        - created
+      properties:
+        id:
+          type: string
+          format: ident
+        sender:
+          type: string
+          format: ident
+        connection:
+          type: string
+          format: ident
+        recipients:
+          type: array
+          items:
+            type: string
+        subject:
+          type: string
+        body:
+          type: string
+        created:
+          type: integer
+          format: date-time
+    SimpleMail:
+      description: |
+        A simple e-mail related to an item.
+
+        The mail may contain the item attachments as mail attachments.
+        If all item attachments should be send, set
+        `addAllAttachments` to `true`. Otherwise set it to `false` and
+        specify a list of file-ids that you want to include. This list
+        is ignored, if `addAllAttachments` is set to `true`.
+      required:
+        - recipients
+        - subject
+        - body
+        - addAllAttachments
+        - attachmentIds
+      properties:
+        recipients:
+          type: array
+          items:
+            type: string
+        subject:
+          type: string
+        body:
+          type: string
+        addAllAttachments:
+          type: boolean
+        attachmentIds:
+          type: array
+          items:
+            type: string
+            format: ident
+    EmailSettingsList:
+      description: |
+        A list of user email settings.
+      required:
+        - items
+      properties:
+        items:
+          type: array
+          items:
+            $ref: "#/components/schemas/EmailSettings"
+    EmailSettings:
+      description: |
+        SMTP settings for sending mail.
+      required:
+        - name
+        - smtpHost
+        - from
+        - sslType
+        - ignoreCertificates
+      properties:
+        name:
+          type: string
+          format: ident
+        smtpHost:
+          type: string
+        smtpPort:
+          type: integer
+          format: int32
+        smtpUser:
+          type: string
+        smtpPassword:
+          type: string
+          format: password
+        from:
+          type: string
+        replyTo:
+          type: string
+        sslType:
+          type: string
+        ignoreCertificates:
+          type: boolean
     CheckFileResult:
       description: |
         Results when searching for file checksums.
@@ -2157,7 +2448,7 @@ components:
     id:
       name: id
       in: path
-      description: A identifier
+      description: An identifier
       required: true
       schema:
         type: string
@@ -2182,3 +2473,17 @@ components:
       required: false
       schema:
         type: string
+    name:
+      name: name
+      in: path
+      description: An e-mail connection name
+      required: true
+      schema:
+        type: string
+    mailId:
+      name: mailId
+      in: path
+      description: The id of a sent mail.
+      required: true
+      schema:
+        type: string
diff --git a/modules/restserver/src/main/resources/logback.xml b/modules/restserver/src/main/resources/logback.xml
index c33ec1f7..f9b2d921 100644
--- a/modules/restserver/src/main/resources/logback.xml
+++ b/modules/restserver/src/main/resources/logback.xml
@@ -8,6 +8,8 @@
   </appender>
 
   <logger name="docspell" level="debug" />
+  <logger name="emil" level="debug"/>
+
   <root level="INFO">
     <appender-ref ref="STDOUT" />
   </root>
diff --git a/modules/restserver/src/main/scala/docspell/restserver/RestServer.scala b/modules/restserver/src/main/scala/docspell/restserver/RestServer.scala
index c88dfa9b..160a92a7 100644
--- a/modules/restserver/src/main/scala/docspell/restserver/RestServer.scala
+++ b/modules/restserver/src/main/scala/docspell/restserver/RestServer.scala
@@ -57,19 +57,22 @@ object RestServer {
       token: AuthToken
   ): HttpRoutes[F] =
     Router(
-      "auth"         -> LoginRoutes.session(restApp.backend.login, cfg),
-      "tag"          -> TagRoutes(restApp.backend, token),
-      "equipment"    -> EquipmentRoutes(restApp.backend, token),
-      "organization" -> OrganizationRoutes(restApp.backend, token),
-      "person"       -> PersonRoutes(restApp.backend, token),
-      "source"       -> SourceRoutes(restApp.backend, token),
-      "user"         -> UserRoutes(restApp.backend, token),
-      "collective"   -> CollectiveRoutes(restApp.backend, token),
-      "queue"        -> JobQueueRoutes(restApp.backend, token),
-      "item"         -> ItemRoutes(restApp.backend, token),
-      "attachment"   -> AttachmentRoutes(restApp.backend, token),
-      "upload"       -> UploadRoutes.secured(restApp.backend, cfg, token),
-      "checkfile"    -> CheckFileRoutes.secured(restApp.backend, token)
+      "auth"           -> LoginRoutes.session(restApp.backend.login, cfg),
+      "tag"            -> TagRoutes(restApp.backend, token),
+      "equipment"      -> EquipmentRoutes(restApp.backend, token),
+      "organization"   -> OrganizationRoutes(restApp.backend, token),
+      "person"         -> PersonRoutes(restApp.backend, token),
+      "source"         -> SourceRoutes(restApp.backend, token),
+      "user"           -> UserRoutes(restApp.backend, token),
+      "collective"     -> CollectiveRoutes(restApp.backend, token),
+      "queue"          -> JobQueueRoutes(restApp.backend, token),
+      "item"           -> ItemRoutes(restApp.backend, token),
+      "attachment"     -> AttachmentRoutes(restApp.backend, token),
+      "upload"         -> UploadRoutes.secured(restApp.backend, cfg, token),
+      "checkfile"      -> CheckFileRoutes.secured(restApp.backend, token),
+      "email/send"     -> MailSendRoutes(restApp.backend, token),
+      "email/settings" -> MailSettingsRoutes(restApp.backend, token),
+      "email/sent"     -> SentMailRoutes(restApp.backend, token)
     )
 
   def openRoutes[F[_]: Effect](cfg: Config, restApp: RestApp[F]): HttpRoutes[F] =
diff --git a/modules/restserver/src/main/scala/docspell/restserver/routes/ItemRoutes.scala b/modules/restserver/src/main/scala/docspell/restserver/routes/ItemRoutes.scala
index a35a69cc..7aee0ea2 100644
--- a/modules/restserver/src/main/scala/docspell/restserver/routes/ItemRoutes.scala
+++ b/modules/restserver/src/main/scala/docspell/restserver/routes/ItemRoutes.scala
@@ -96,15 +96,15 @@ object ItemRoutes {
       case req @ POST -> Root / Ident(id) / "notes" =>
         for {
           text <- req.as[OptionalText]
-          res  <- backend.item.setNotes(id, text.text, user.account.collective)
-          resp <- Ok(Conversions.basicResult(res, "Concerned equipment updated"))
+          res  <- backend.item.setNotes(id, text.text.notEmpty, user.account.collective)
+          resp <- Ok(Conversions.basicResult(res, "Notes updated"))
         } yield resp
 
       case req @ POST -> Root / Ident(id) / "name" =>
         for {
           text <- req.as[OptionalText]
-          res  <- backend.item.setName(id, text.text.getOrElse(""), user.account.collective)
-          resp <- Ok(Conversions.basicResult(res, "Concerned equipment updated"))
+          res  <- backend.item.setName(id, text.text.notEmpty.getOrElse(""), user.account.collective)
+          resp <- Ok(Conversions.basicResult(res, "Name updated"))
         } yield resp
 
       case req @ POST -> Root / Ident(id) / "duedate" =>
@@ -138,4 +138,10 @@ object ItemRoutes {
         } yield resp
     }
   }
+
+
+  final implicit class OptionString(opt: Option[String]) {
+    def notEmpty: Option[String] =
+      opt.map(_.trim).filter(_.nonEmpty)
+  }
 }
diff --git a/modules/restserver/src/main/scala/docspell/restserver/routes/MailSendRoutes.scala b/modules/restserver/src/main/scala/docspell/restserver/routes/MailSendRoutes.scala
new file mode 100644
index 00000000..3d7a08e3
--- /dev/null
+++ b/modules/restserver/src/main/scala/docspell/restserver/routes/MailSendRoutes.scala
@@ -0,0 +1,56 @@
+package docspell.restserver.routes
+
+import cats.effect._
+import cats.implicits._
+import org.http4s._
+import org.http4s.dsl.Http4sDsl
+import org.http4s.circe.CirceEntityEncoder._
+import org.http4s.circe.CirceEntityDecoder._
+
+import docspell.backend.BackendApp
+import docspell.backend.auth.AuthToken
+import docspell.backend.ops.OMail.{AttachSelection, ItemMail}
+import docspell.backend.ops.SendResult
+import docspell.common._
+import docspell.restapi.model._
+import docspell.store.EmilUtil
+
+object MailSendRoutes {
+
+  def apply[F[_]: Effect](backend: BackendApp[F], user: AuthToken): HttpRoutes[F] = {
+    val dsl = new Http4sDsl[F] {}
+    import dsl._
+
+    HttpRoutes.of {
+      case req @ POST -> Root / Ident(name) / Ident(id) =>
+        for {
+          in <- req.as[SimpleMail]
+          mail = convertIn(id, in)
+          res <- mail.traverse(m => backend.mail.sendMail(user.account, name, m))
+          resp <- res.fold(
+            err => Ok(BasicResult(false, s"Invalid mail data: $err")),
+            res => Ok(convertOut(res))
+          )
+        } yield resp
+    }
+  }
+
+  def convertIn(item: Ident, s: SimpleMail): Either[String, ItemMail] =
+    for {
+      rec     <- s.recipients.traverse(EmilUtil.readMailAddress)
+      fileIds <- s.attachmentIds.traverse(Ident.fromString)
+      sel = if (s.addAllAttachments) AttachSelection.All else AttachSelection.Selected(fileIds)
+    } yield ItemMail(item, s.subject, rec, s.body, sel)
+
+  def convertOut(res: SendResult): BasicResult =
+    res match {
+      case SendResult.Success(_) =>
+        BasicResult(true, "Mail sent.")
+      case SendResult.SendFailure(ex) =>
+        BasicResult(false, s"Mail sending failed: ${ex.getMessage}")
+      case SendResult.StoreFailure(ex) =>
+        BasicResult(false, s"Mail was sent, but could not be store to database: ${ex.getMessage}")
+      case SendResult.NotFound =>
+        BasicResult(false, s"There was no mail-connection or item found.")
+    }
+}
diff --git a/modules/restserver/src/main/scala/docspell/restserver/routes/MailSettingsRoutes.scala b/modules/restserver/src/main/scala/docspell/restserver/routes/MailSettingsRoutes.scala
new file mode 100644
index 00000000..ffb26b49
--- /dev/null
+++ b/modules/restserver/src/main/scala/docspell/restserver/routes/MailSettingsRoutes.scala
@@ -0,0 +1,123 @@
+package docspell.restserver.routes
+
+import cats.effect._
+import cats.implicits._
+import cats.data.OptionT
+import org.http4s._
+import org.http4s.dsl.Http4sDsl
+import org.http4s.circe.CirceEntityEncoder._
+import org.http4s.circe.CirceEntityDecoder._
+import emil.MailAddress
+
+import docspell.backend.BackendApp
+import docspell.backend.auth.AuthToken
+import docspell.backend.ops.OMail
+import docspell.common._
+import docspell.restapi.model._
+import docspell.store.records.RUserEmail
+import docspell.store.EmilUtil
+import docspell.restserver.conv.Conversions
+
+object MailSettingsRoutes {
+
+  def apply[F[_]: Effect](backend: BackendApp[F], user: AuthToken): HttpRoutes[F] = {
+    val dsl = new Http4sDsl[F] {}
+    import dsl._
+
+    HttpRoutes.of {
+      case req @ GET -> Root =>
+        val q = req.params.get("q").map(_.trim).filter(_.nonEmpty)
+        for {
+          list <- backend.mail.getSettings(user.account, q)
+          res = list.map(convert)
+          resp <- Ok(EmailSettingsList(res.toList))
+        } yield resp
+
+      case GET -> Root / Ident(name) =>
+        (for {
+          ems  <- backend.mail.findSettings(user.account, name)
+          resp <- OptionT.liftF(Ok(convert(ems)))
+        } yield resp).getOrElseF(NotFound())
+
+      case req @ POST -> Root =>
+        (for {
+          in <- OptionT.liftF(req.as[EmailSettings])
+          ru = makeSettings(in)
+          up <- OptionT.liftF(ru.traverse(r => backend.mail.createSettings(user.account, r)))
+          resp <- OptionT.liftF(
+            Ok(
+              up.fold(
+                err => BasicResult(false, err),
+                ar => Conversions.basicResult(ar, "Mail settings stored.")
+              )
+            )
+          )
+        } yield resp).getOrElseF(NotFound())
+
+      case req @ PUT -> Root / Ident(name) =>
+        (for {
+          in <- OptionT.liftF(req.as[EmailSettings])
+          ru = makeSettings(in)
+          up <- OptionT.liftF(ru.traverse(r => backend.mail.updateSettings(user.account, name, r)))
+          resp <- OptionT.liftF(
+            Ok(
+              up.fold(
+                err => BasicResult(false, err),
+                n =>
+                  if (n > 0) BasicResult(true, "Mail settings stored.")
+                  else BasicResult(false, "Mail settings could not be saved")
+              )
+            )
+          )
+        } yield resp).getOrElseF(NotFound())
+
+      case DELETE -> Root / Ident(name) =>
+        for {
+          n <- backend.mail.deleteSettings(user.account, name)
+          resp <- Ok(
+            if (n > 0) BasicResult(true, "Mail settings removed")
+            else BasicResult(false, "Mail settings could not be removed")
+          )
+        } yield resp
+    }
+
+  }
+
+  def convert(ru: RUserEmail): EmailSettings =
+    EmailSettings(
+      ru.name,
+      ru.smtpHost,
+      ru.smtpPort,
+      ru.smtpUser,
+      ru.smtpPassword,
+      EmilUtil.mailAddressString(ru.mailFrom),
+      ru.mailReplyTo.map(EmilUtil.mailAddressString _),
+      EmilUtil.sslTypeString(ru.smtpSsl),
+      !ru.smtpCertCheck
+    )
+
+  def makeSettings(ems: EmailSettings): Either[String, OMail.SmtpSettings] = {
+    def readMail(str: String): Either[String, MailAddress] =
+      EmilUtil.readMailAddress(str).left.map(err => s"E-Mail address '$str' invalid: $err")
+
+    def readMailOpt(str: Option[String]): Either[String, Option[MailAddress]] =
+      str.traverse(readMail)
+
+    for {
+      from <- readMail(ems.from)
+      repl <- readMailOpt(ems.replyTo)
+      sslt <- EmilUtil.readSSLType(ems.sslType)
+    } yield OMail.SmtpSettings(
+      ems.name,
+      ems.smtpHost,
+      ems.smtpPort,
+      ems.smtpUser,
+      ems.smtpPassword,
+      sslt,
+      !ems.ignoreCertificates,
+      from,
+      repl
+    )
+
+  }
+}
diff --git a/modules/restserver/src/main/scala/docspell/restserver/routes/SentMailRoutes.scala b/modules/restserver/src/main/scala/docspell/restserver/routes/SentMailRoutes.scala
new file mode 100644
index 00000000..01f22c45
--- /dev/null
+++ b/modules/restserver/src/main/scala/docspell/restserver/routes/SentMailRoutes.scala
@@ -0,0 +1,54 @@
+package docspell.restserver.routes
+
+import cats.effect._
+import cats.implicits._
+import cats.data.OptionT
+import org.http4s._
+import org.http4s.dsl.Http4sDsl
+import org.http4s.circe.CirceEntityEncoder._
+
+import docspell.backend.BackendApp
+import docspell.backend.auth.AuthToken
+import docspell.backend.ops.OMail.Sent
+import docspell.common._
+import docspell.restapi.model._
+import docspell.store.EmilUtil
+
+object SentMailRoutes {
+
+  def apply[F[_]: Effect](backend: BackendApp[F], user: AuthToken): HttpRoutes[F] = {
+    val dsl = new Http4sDsl[F] {}
+    import dsl._
+
+    HttpRoutes.of {
+      case GET -> Root / "item" / Ident(id) =>
+        for {
+          all <- backend.mail.getSentMailsForItem(user.account, id)
+          resp <- Ok(SentMails(all.map(convert).toList))
+        } yield resp
+
+      case GET -> Root / "mail" / Ident(mailId) =>
+        (for {
+          mail <- backend.mail.getSentMail(user.account, mailId)
+          resp <- OptionT.liftF(Ok(convert(mail)))
+        } yield resp).getOrElseF(NotFound())
+
+      case DELETE -> Root / "mail" / Ident(mailId) =>
+        for {
+          n <- backend.mail.deleteSentMail(user.account, mailId)
+          resp <- Ok(BasicResult(n > 0, s"Mails deleted: $n"))
+        } yield resp
+    }
+  }
+
+  def convert(s: Sent): SentMail =
+    SentMail(
+      s.id,
+      s.senderLogin,
+      s.connectionName,
+      s.recipients.map(EmilUtil.mailAddressString),
+      s.subject,
+      s.body,
+      s.created
+    )
+}
diff --git a/modules/store/src/main/resources/db/migration/postgresql/V1.1.0__useremail.sql b/modules/store/src/main/resources/db/migration/postgresql/V1.1.0__useremail.sql
new file mode 100644
index 00000000..75812938
--- /dev/null
+++ b/modules/store/src/main/resources/db/migration/postgresql/V1.1.0__useremail.sql
@@ -0,0 +1,39 @@
+CREATE TABLE "useremail" (
+  "id" varchar(254) not null primary key,
+  "uid" varchar(254) not null,
+  "name" varchar(254) not null,
+  "smtp_host" varchar(254) not null,
+  "smtp_port" int,
+  "smtp_user" varchar(254),
+  "smtp_password" varchar(254),
+  "smtp_ssl" varchar(254) not null,
+  "smtp_certcheck" boolean not null,
+  "mail_from" varchar(254) not null,
+  "mail_replyto" varchar(254),
+  "created" timestamp not null,
+  unique ("uid", "name"),
+  foreign key ("uid") references "user_"("uid")
+);
+
+CREATE TABLE "sentmail" (
+  "id" varchar(254) not null primary key,
+  "uid" varchar(254) not null,
+  "message_id" varchar(254) not null,
+  "sender" varchar(254) not null,
+  "conn_name" varchar(254) not null,
+  "subject" varchar(254) not null,
+  "recipients" varchar(254) not null,
+  "body" text not null,
+  "created" timestamp not null,
+  foreign key("uid") references "user_"("uid")
+);
+
+CREATE TABLE "sentmailitem" (
+  "id" varchar(254) not null primary key,
+  "item_id" varchar(254) not null,
+  "sentmail_id" varchar(254) not null,
+  "created" timestamp not null,
+  unique ("item_id", "sentmail_id"),
+  foreign key("item_id") references "item"("itemid"),
+  foreign key("sentmail_id") references "sentmail"("id")
+);
diff --git a/modules/store/src/main/scala/docspell/store/EmilUtil.scala b/modules/store/src/main/scala/docspell/store/EmilUtil.scala
new file mode 100644
index 00000000..749a041a
--- /dev/null
+++ b/modules/store/src/main/scala/docspell/store/EmilUtil.scala
@@ -0,0 +1,38 @@
+package docspell.store
+
+import cats.implicits._
+import emil._
+import emil.javamail.syntax._
+
+object EmilUtil {
+
+  def readSSLType(str: String): Either[String, SSLType] =
+    str.toLowerCase match {
+      case "ssl"      => Right(SSLType.SSL)
+      case "starttls" => Right(SSLType.StartTLS)
+      case "none"     => Right(SSLType.NoEncryption)
+      case _          => Left(s"Invalid ssl-type: $str")
+    }
+
+  def unsafeReadSSLType(str: String): SSLType =
+    readSSLType(str).fold(sys.error, identity)
+
+  def sslTypeString(st: SSLType): String =
+    st match {
+      case SSLType.SSL          => "ssl"
+      case SSLType.StartTLS     => "starttls"
+      case SSLType.NoEncryption => "none"
+    }
+
+  def readMailAddress(str: String): Either[String, MailAddress] =
+    MailAddress.parse(str)
+
+  def unsafeReadMailAddress(str: String): MailAddress =
+    readMailAddress(str).fold(sys.error, identity)
+
+  def readMultipleAddresses(str: String): Either[String, List[MailAddress]] =
+    str.split(',').toList.map(_.trim).traverse(readMailAddress)
+
+  def mailAddressString(ma: MailAddress): String =
+    ma.asUnicodeString
+}
diff --git a/modules/store/src/main/scala/docspell/store/impl/DoobieMeta.scala b/modules/store/src/main/scala/docspell/store/impl/DoobieMeta.scala
index b731406e..62f058cd 100644
--- a/modules/store/src/main/scala/docspell/store/impl/DoobieMeta.scala
+++ b/modules/store/src/main/scala/docspell/store/impl/DoobieMeta.scala
@@ -2,16 +2,15 @@ package docspell.store.impl
 
 import java.time.format.DateTimeFormatter
 import java.time.{Instant, LocalDate}
-
-import docspell.common.Timestamp
-
-import docspell.common._
+import io.circe.{Decoder, Encoder}
 import doobie._
-//import doobie.implicits.javatime._
 import doobie.implicits.legacy.instant._
 import doobie.util.log.Success
-import io.circe.{Decoder, Encoder}
+import emil.{MailAddress, SSLType}
+
+import docspell.common._
 import docspell.common.syntax.all._
+import docspell.store.EmilUtil
 
 trait DoobieMeta {
 
@@ -88,9 +87,21 @@ trait DoobieMeta {
 
   implicit val metaLanguage: Meta[Language] =
     Meta[String].imap(Language.unsafe)(_.iso3)
+
+  implicit val sslType: Meta[SSLType] =
+    Meta[String].imap(EmilUtil.unsafeReadSSLType)(EmilUtil.sslTypeString)
+
+  implicit val mailAddress: Meta[MailAddress] =
+    Meta[String].imap(EmilUtil.unsafeReadMailAddress)(EmilUtil.mailAddressString)
+
+  implicit def mailAddressList: Meta[List[MailAddress]] =
+    Meta[String].imap(str => str.split(',').toList.map(_.trim).map(EmilUtil.unsafeReadMailAddress))(
+      lma => lma.map(EmilUtil.mailAddressString).mkString(",")
+    )
 }
 
 object DoobieMeta extends DoobieMeta {
   import org.log4s._
   private val logger = getLogger
+
 }
diff --git a/modules/store/src/main/scala/docspell/store/impl/DoobieSyntax.scala b/modules/store/src/main/scala/docspell/store/impl/DoobieSyntax.scala
index 47e61345..4eef507f 100644
--- a/modules/store/src/main/scala/docspell/store/impl/DoobieSyntax.scala
+++ b/modules/store/src/main/scala/docspell/store/impl/DoobieSyntax.scala
@@ -65,12 +65,6 @@ trait DoobieSyntax {
     Fragment.const("SELECT DISTINCT(") ++ commas(cols.map(_.f)) ++
       Fragment.const(") FROM ") ++ table ++ this.where(where)
 
-//  def selectJoinCollective(cols: Seq[Column], fkCid: Column, table: Fragment, wh: Fragment): Fragment =
-//    selectSimple(cols.map(_.prefix("a"))
-//      , table ++ fr"a," ++ RCollective.table ++ fr"b"
-//      , if (isEmpty(wh)) fkCid.prefix("a") is RCollective.Columns.id.prefix("b")
-//        else and(wh, fkCid.prefix("a") is RCollective.Columns.id.prefix("b")))
-
   def selectCount(col: Column, table: Fragment, where: Fragment): Fragment =
     Fragment.const("SELECT COUNT(") ++ col.f ++ Fragment.const(") FROM ") ++ table ++ this.where(
       where
diff --git a/modules/store/src/main/scala/docspell/store/queries/QMails.scala b/modules/store/src/main/scala/docspell/store/queries/QMails.scala
new file mode 100644
index 00000000..6053df10
--- /dev/null
+++ b/modules/store/src/main/scala/docspell/store/queries/QMails.scala
@@ -0,0 +1,64 @@
+package docspell.store.queries
+
+import cats.data.OptionT
+import doobie._
+import doobie.implicits._
+
+import docspell.common._
+import docspell.store.impl.Column
+import docspell.store.impl.Implicits._
+import docspell.store.records.{RItem, RSentMail, RSentMailItem, RUser}
+
+object QMails {
+
+  def delete(coll: Ident, mailId: Ident): ConnectionIO[Int] =
+    (for {
+      m <- OptionT(findMail(coll, mailId))
+      k <- OptionT.liftF(RSentMailItem.deleteMail(mailId))
+      n <- OptionT.liftF(RSentMail.delete(m._1.id))
+    } yield k + n).getOrElse(0)
+
+  def findMail(coll: Ident, mailId: Ident): ConnectionIO[Option[(RSentMail, Ident)]] = {
+    val iColl = RItem.Columns.cid.prefix("i")
+    val mId   = RSentMail.Columns.id.prefix("m")
+
+    val (cols, from) = partialFind
+
+    val cond = Seq(mId.is(mailId), iColl.is(coll))
+
+    selectSimple(cols, from, and(cond)).query[(RSentMail, Ident)].option
+  }
+
+  def findMails(coll: Ident, itemId: Ident): ConnectionIO[Vector[(RSentMail, Ident)]] = {
+    val iColl    = RItem.Columns.cid.prefix("i")
+    val tItem    = RSentMailItem.Columns.itemId.prefix("t")
+    val mCreated = RSentMail.Columns.created.prefix("m")
+
+    val (cols, from) = partialFind
+
+    val cond = Seq(tItem.is(itemId), iColl.is(coll))
+
+    (selectSimple(cols, from, and(cond)) ++ orderBy(mCreated.f) ++ fr"DESC")
+      .query[(RSentMail, Ident)]
+      .to[Vector]
+  }
+
+  private def partialFind: (Seq[Column], Fragment) = {
+    val iId    = RItem.Columns.id.prefix("i")
+    val tItem  = RSentMailItem.Columns.itemId.prefix("t")
+    val tMail  = RSentMailItem.Columns.sentMailId.prefix("t")
+    val mId    = RSentMail.Columns.id.prefix("m")
+    val mUser  = RSentMail.Columns.uid.prefix("m")
+    val uId    = RUser.Columns.uid.prefix("u")
+    val uLogin = RUser.Columns.login.prefix("u")
+
+    val cols = RSentMail.Columns.all.map(_.prefix("m")) :+ uLogin
+    val from = RSentMail.table ++ fr"m INNER JOIN" ++
+      RSentMailItem.table ++ fr"t ON" ++ tMail.is(mId) ++
+      fr"INNER JOIN" ++ RItem.table ++ fr"i ON" ++ tItem.is(iId) ++
+      fr"INNER JOIN" ++ RUser.table ++ fr"u ON" ++ uId.is(mUser)
+
+    (cols, from)
+  }
+
+}
diff --git a/modules/store/src/main/scala/docspell/store/records/RAttachment.scala b/modules/store/src/main/scala/docspell/store/records/RAttachment.scala
index 52f71d30..ee193e69 100644
--- a/modules/store/src/main/scala/docspell/store/records/RAttachment.scala
+++ b/modules/store/src/main/scala/docspell/store/records/RAttachment.scala
@@ -64,6 +64,26 @@ object RAttachment {
     q.query[RAttachment].to[Vector]
   }
 
+  def findByItemAndCollectiveWithMeta(
+      id: Ident,
+      coll: Ident
+  ): ConnectionIO[Vector[(RAttachment, FileMeta)]] = {
+    import bitpeace.sql._
+
+    val cols      = all.map(_.prefix("a")) ++ RFileMeta.Columns.all.map(_.prefix("m"))
+    val afileMeta = fileId.prefix("a")
+    val aItem     = itemId.prefix("a")
+    val mId       = RFileMeta.Columns.id.prefix("m")
+    val iId       = RItem.Columns.id.prefix("i")
+    val iColl     = RItem.Columns.cid.prefix("i")
+
+    val from = table ++ fr"a INNER JOIN" ++ RFileMeta.table ++ fr"m ON" ++ afileMeta.is(mId) ++
+      fr"INNER JOIN" ++ RItem.table ++ fr"i ON" ++ aItem.is(iId)
+    val cond = Seq(aItem.is(id), iColl.is(coll))
+
+    selectSimple(cols, from, and(cond)).query[(RAttachment, FileMeta)].to[Vector]
+  }
+
   def findByItemWithMeta(id: Ident): ConnectionIO[Vector[(RAttachment, FileMeta)]] = {
     import bitpeace.sql._
 
diff --git a/modules/store/src/main/scala/docspell/store/records/RFileMeta.scala b/modules/store/src/main/scala/docspell/store/records/RFileMeta.scala
new file mode 100644
index 00000000..e6f206e5
--- /dev/null
+++ b/modules/store/src/main/scala/docspell/store/records/RFileMeta.scala
@@ -0,0 +1,22 @@
+package docspell.store.records
+
+import doobie.implicits._
+import docspell.store.impl._
+
+object RFileMeta {
+
+  val table = fr"filemeta"
+
+  object Columns {
+    val id = Column("id")
+    val timestamp = Column("timestamp")
+    val mimetype = Column("mimetype")
+    val length = Column("length")
+    val checksum = Column("checksum")
+    val chunks = Column("chunks")
+    val chunksize = Column("chunksize")
+
+    val all = List(id, timestamp, mimetype, length, checksum, chunks, chunksize)
+
+  }
+}
diff --git a/modules/store/src/main/scala/docspell/store/records/RItem.scala b/modules/store/src/main/scala/docspell/store/records/RItem.scala
index 7d9dafda..bf447317 100644
--- a/modules/store/src/main/scala/docspell/store/records/RItem.scala
+++ b/modules/store/src/main/scala/docspell/store/records/RItem.scala
@@ -262,4 +262,7 @@ object RItem {
 
   def deleteByIdAndCollective(itemId: Ident, coll: Ident): ConnectionIO[Int] =
     deleteFrom(table, and(id.is(itemId), cid.is(coll))).update.run
+
+  def existsById(itemId: Ident): ConnectionIO[Boolean] =
+    selectCount(id, table, id.is(itemId)).query[Int].unique.map(_ > 0)
 }
diff --git a/modules/store/src/main/scala/docspell/store/records/RSentMail.scala b/modules/store/src/main/scala/docspell/store/records/RSentMail.scala
new file mode 100644
index 00000000..a0679b20
--- /dev/null
+++ b/modules/store/src/main/scala/docspell/store/records/RSentMail.scala
@@ -0,0 +1,100 @@
+package docspell.store.records
+
+import fs2.Stream
+import cats.effect._
+import cats.implicits._
+import doobie._
+import doobie.implicits._
+import docspell.common._
+import docspell.store.impl.Column
+import docspell.store.impl.Implicits._
+import emil.MailAddress
+import cats.data.OptionT
+
+case class RSentMail(
+    id: Ident,
+    uid: Ident,
+    messageId: String,
+    sender: MailAddress,
+    connName: Ident,
+    subject: String,
+    recipients: List[MailAddress],
+    body: String,
+    created: Timestamp
+) {}
+
+object RSentMail {
+
+  def apply[F[_]: Sync](
+      uid: Ident,
+      messageId: String,
+      sender: MailAddress,
+      connName: Ident,
+      subject: String,
+      recipients: List[MailAddress],
+      body: String
+  ): F[RSentMail] =
+    for {
+      id  <- Ident.randomId[F]
+      now <- Timestamp.current[F]
+    } yield RSentMail(id, uid, messageId, sender, connName, subject, recipients, body, now)
+
+  def forItem(
+      itemId: Ident,
+      accId: AccountId,
+      messageId: String,
+      sender: MailAddress,
+      connName: Ident,
+      subject: String,
+      recipients: List[MailAddress],
+      body: String
+  ): OptionT[ConnectionIO, (RSentMail, RSentMailItem)] =
+    for {
+      user <- OptionT(RUser.findByAccount(accId))
+      sm <- OptionT.liftF(
+        RSentMail[ConnectionIO](user.uid, messageId, sender, connName, subject, recipients, body)
+      )
+      si <- OptionT.liftF(RSentMailItem[ConnectionIO](itemId, sm.id, Some(sm.created)))
+    } yield (sm, si)
+
+  val table = fr"sentmail"
+
+  object Columns {
+    val id         = Column("id")
+    val uid        = Column("uid")
+    val messageId  = Column("message_id")
+    val sender     = Column("sender")
+    val connName   = Column("conn_name")
+    val subject    = Column("subject")
+    val recipients = Column("recipients")
+    val body       = Column("body")
+    val created    = Column("created")
+
+    val all = List(
+      id,
+      uid,
+      messageId,
+      sender,
+      connName,
+      subject,
+      recipients,
+      body,
+      created
+    )
+  }
+
+  import Columns._
+
+  def insert(v: RSentMail): ConnectionIO[Int] =
+    insertRow(
+      table,
+      all,
+      sql"${v.id},${v.uid},${v.messageId},${v.sender},${v.connName},${v.subject},${v.recipients},${v.body},${v.created}"
+    ).update.run
+
+  def findByUser(userId: Ident): Stream[ConnectionIO, RSentMail] =
+    selectSimple(all, table, uid.is(userId)).query[RSentMail].stream
+
+  def delete(mailId: Ident): ConnectionIO[Int] =
+    deleteFrom(table, id.is(mailId)).update.run
+}
diff --git a/modules/store/src/main/scala/docspell/store/records/RSentMailItem.scala b/modules/store/src/main/scala/docspell/store/records/RSentMailItem.scala
new file mode 100644
index 00000000..5f796c6e
--- /dev/null
+++ b/modules/store/src/main/scala/docspell/store/records/RSentMailItem.scala
@@ -0,0 +1,57 @@
+package docspell.store.records
+
+import cats.effect._
+import cats.implicits._
+import doobie._
+import doobie.implicits._
+import docspell.common._
+import docspell.store.impl.Column
+import docspell.store.impl.Implicits._
+
+case class RSentMailItem(
+    id: Ident,
+    itemId: Ident,
+    sentMailId: Ident,
+    created: Timestamp
+) {}
+
+object RSentMailItem {
+
+  def apply[F[_]: Sync](
+      itemId: Ident,
+      sentmailId: Ident,
+      created: Option[Timestamp] = None
+  ): F[RSentMailItem] =
+    for {
+      id  <- Ident.randomId[F]
+      now <- created.map(_.pure[F]).getOrElse(Timestamp.current[F])
+    } yield RSentMailItem(id, itemId, sentmailId, now)
+
+  val table = fr"sentmailitem"
+
+  object Columns {
+    val id         = Column("id")
+    val itemId     = Column("item_id")
+    val sentMailId = Column("sentmail_id")
+    val created    = Column("created")
+
+    val all = List(
+      id,
+      itemId,
+      sentMailId,
+      created
+    )
+  }
+
+  import Columns._
+
+  def insert(v: RSentMailItem): ConnectionIO[Int] =
+    insertRow(
+      table,
+      all,
+      sql"${v.id},${v.itemId},${v.sentMailId},${v.created}"
+    ).update.run
+
+  def deleteMail(mailId: Ident): ConnectionIO[Int] =
+    deleteFrom(table, sentMailId.is(mailId)).update.run
+}
diff --git a/modules/store/src/main/scala/docspell/store/records/RUserEmail.scala b/modules/store/src/main/scala/docspell/store/records/RUserEmail.scala
new file mode 100644
index 00000000..e8fcc0b7
--- /dev/null
+++ b/modules/store/src/main/scala/docspell/store/records/RUserEmail.scala
@@ -0,0 +1,212 @@
+package docspell.store.records
+
+import doobie._
+import doobie.implicits._
+import cats.effect._
+import cats.implicits._
+import cats.data.OptionT
+import docspell.common._
+import docspell.store.impl.Column
+import docspell.store.impl.Implicits._
+import emil.{MailAddress, MailConfig, SSLType}
+
+case class RUserEmail(
+    id: Ident,
+    uid: Ident,
+    name: Ident,
+    smtpHost: String,
+    smtpPort: Option[Int],
+    smtpUser: Option[String],
+    smtpPassword: Option[Password],
+    smtpSsl: SSLType,
+    smtpCertCheck: Boolean,
+    mailFrom: MailAddress,
+    mailReplyTo: Option[MailAddress],
+    created: Timestamp
+) {
+
+  def toMailConfig: MailConfig = {
+    val port = smtpPort.map(p => s":$p").getOrElse("")
+    MailConfig(
+      s"smtp://$smtpHost$port",
+      smtpUser.getOrElse(""),
+      smtpPassword.map(_.pass).getOrElse(""),
+      smtpSsl,
+      !smtpCertCheck
+    )
+  }
+}
+
+object RUserEmail {
+
+  def apply[F[_]: Sync](
+      uid: Ident,
+      name: Ident,
+      smtpHost: String,
+      smtpPort: Option[Int],
+      smtpUser: Option[String],
+      smtpPassword: Option[Password],
+      smtpSsl: SSLType,
+      smtpCertCheck: Boolean,
+      mailFrom: MailAddress,
+      mailReplyTo: Option[MailAddress]
+  ): F[RUserEmail] =
+    for {
+      now <- Timestamp.current[F]
+      id  <- Ident.randomId[F]
+    } yield RUserEmail(
+      id,
+      uid,
+      name,
+      smtpHost,
+      smtpPort,
+      smtpUser,
+      smtpPassword,
+      smtpSsl,
+      smtpCertCheck,
+      mailFrom,
+      mailReplyTo,
+      now
+    )
+
+  def fromAccount(
+      accId: AccountId,
+      name: Ident,
+      smtpHost: String,
+      smtpPort: Option[Int],
+      smtpUser: Option[String],
+      smtpPassword: Option[Password],
+      smtpSsl: SSLType,
+      smtpCertCheck: Boolean,
+      mailFrom: MailAddress,
+      mailReplyTo: Option[MailAddress]
+  ): OptionT[ConnectionIO, RUserEmail] =
+    for {
+      now  <- OptionT.liftF(Timestamp.current[ConnectionIO])
+      id   <- OptionT.liftF(Ident.randomId[ConnectionIO])
+      user <- OptionT(RUser.findByAccount(accId))
+    } yield RUserEmail(
+      id,
+      user.uid,
+      name,
+      smtpHost,
+      smtpPort,
+      smtpUser,
+      smtpPassword,
+      smtpSsl,
+      smtpCertCheck,
+      mailFrom,
+      mailReplyTo,
+      now
+    )
+
+  val table = fr"useremail"
+
+  object Columns {
+    val id            = Column("id")
+    val uid           = Column("uid")
+    val name          = Column("name")
+    val smtpHost      = Column("smtp_host")
+    val smtpPort      = Column("smtp_port")
+    val smtpUser      = Column("smtp_user")
+    val smtpPass      = Column("smtp_password")
+    val smtpSsl       = Column("smtp_ssl")
+    val smtpCertCheck = Column("smtp_certcheck")
+    val mailFrom      = Column("mail_from")
+    val mailReplyTo   = Column("mail_replyto")
+    val created       = Column("created")
+
+    val all = List(
+      id,
+      uid,
+      name,
+      smtpHost,
+      smtpPort,
+      smtpUser,
+      smtpPass,
+      smtpSsl,
+      smtpCertCheck,
+      mailFrom,
+      mailReplyTo,
+      created
+    )
+  }
+
+  import Columns._
+
+  def insert(v: RUserEmail): ConnectionIO[Int] =
+    insertRow(
+      table,
+      all,
+      sql"${v.id},${v.uid},${v.name},${v.smtpHost},${v.smtpPort},${v.smtpUser},${v.smtpPassword},${v.smtpSsl},${v.smtpCertCheck},${v.mailFrom},${v.mailReplyTo},${v.created}"
+    ).update.run
+
+  def update(eId: Ident, v: RUserEmail): ConnectionIO[Int] =
+    updateRow(
+      table,
+      id.is(eId),
+      commas(
+        name.setTo(v.name),
+        smtpHost.setTo(v.smtpHost),
+        smtpPort.setTo(v.smtpPort),
+        smtpUser.setTo(v.smtpUser),
+        smtpPass.setTo(v.smtpPassword),
+        smtpSsl.setTo(v.smtpSsl),
+        smtpCertCheck.setTo(v.smtpCertCheck),
+        mailFrom.setTo(v.mailFrom),
+        mailReplyTo.setTo(v.mailReplyTo)
+      )
+    ).update.run
+
+  def findByUser(userId: Ident): ConnectionIO[Vector[RUserEmail]] =
+    selectSimple(all, table, uid.is(userId)).query[RUserEmail].to[Vector]
+
+  private def findByAccount0(
+      accId: AccountId,
+      nameQ: Option[String],
+      exact: Boolean
+  ): Query0[RUserEmail] = {
+    val mUid   = uid.prefix("m")
+    val mName  = name.prefix("m")
+    val uId    = RUser.Columns.uid.prefix("u")
+    val uColl  = RUser.Columns.cid.prefix("u")
+    val uLogin = RUser.Columns.login.prefix("u")
+    val from   = table ++ fr"m INNER JOIN" ++ RUser.table ++ fr"u ON" ++ mUid.is(uId)
+    val cond = Seq(uColl.is(accId.collective), uLogin.is(accId.user)) ++ (nameQ match {
+      case Some(str) if exact  => Seq(mName.is(str))
+      case Some(str) if !exact => Seq(mName.lowerLike(s"%${str.toLowerCase}%"))
+      case None                => Seq.empty
+    })
+
+    (selectSimple(all.map(_.prefix("m")), from, and(cond)) ++ orderBy(mName.f)).query[RUserEmail]
+  }
+
+  def findByAccount(
+      accId: AccountId,
+      nameQ: Option[String]
+  ): ConnectionIO[Vector[RUserEmail]] =
+    findByAccount0(accId, nameQ, false).to[Vector]
+
+  def getByName(accId: AccountId, name: Ident): ConnectionIO[Option[RUserEmail]] =
+    findByAccount0(accId, Some(name.id), true).option
+
+  def delete(accId: AccountId, connName: Ident): ConnectionIO[Int] = {
+    val uId    = RUser.Columns.uid
+    val uColl  = RUser.Columns.cid
+    val uLogin = RUser.Columns.login
+    val cond   = Seq(uColl.is(accId.collective), uLogin.is(accId.user))
+
+    deleteFrom(
+      table,
+      fr"uid in (" ++ selectSimple(Seq(uId), RUser.table, and(cond)) ++ fr") AND" ++ name.is(
+        connName
+      )
+    ).update.run
+  }
+
+  def exists(accId: AccountId, name: Ident): ConnectionIO[Boolean] =
+    getByName(accId, name).map(_.isDefined)
+
+  def exists(userId: Ident, connName: Ident): ConnectionIO[Boolean] =
+    selectCount(id, table, and(uid.is(userId), name.is(connName))).query[Int].unique.map(_ > 0)
+}
diff --git a/modules/webapp/src/main/elm/Api.elm b/modules/webapp/src/main/elm/Api.elm
index 31bb7eff..fe364cff 100644
--- a/modules/webapp/src/main/elm/Api.elm
+++ b/modules/webapp/src/main/elm/Api.elm
@@ -1,8 +1,10 @@
 module Api exposing
     ( cancelJob
     , changePassword
+    , createMailSettings
     , deleteEquip
     , deleteItem
+    , deleteMailSettings
     , deleteOrg
     , deletePerson
     , deleteSource
@@ -15,10 +17,12 @@ module Api exposing
     , getItemProposals
     , getJobQueueState
     , getJobQueueStateIn
+    , getMailSettings
     , getOrgLight
     , getOrganizations
     , getPersons
     , getPersonsLight
+    , getSentMails
     , getSources
     , getTags
     , getUsers
@@ -37,6 +41,7 @@ module Api exposing
     , putUser
     , refreshSession
     , register
+    , sendMail
     , setCollectiveSettings
     , setConcEquip
     , setConcPerson
@@ -60,6 +65,8 @@ import Api.Model.BasicResult exposing (BasicResult)
 import Api.Model.Collective exposing (Collective)
 import Api.Model.CollectiveSettings exposing (CollectiveSettings)
 import Api.Model.DirectionValue exposing (DirectionValue)
+import Api.Model.EmailSettings exposing (EmailSettings)
+import Api.Model.EmailSettingsList exposing (EmailSettingsList)
 import Api.Model.Equipment exposing (Equipment)
 import Api.Model.EquipmentList exposing (EquipmentList)
 import Api.Model.GenInvite exposing (GenInvite)
@@ -81,6 +88,8 @@ import Api.Model.Person exposing (Person)
 import Api.Model.PersonList exposing (PersonList)
 import Api.Model.ReferenceList exposing (ReferenceList)
 import Api.Model.Registration exposing (Registration)
+import Api.Model.SentMails exposing (SentMails)
+import Api.Model.SimpleMail exposing (SimpleMail)
 import Api.Model.Source exposing (Source)
 import Api.Model.SourceList exposing (SourceList)
 import Api.Model.Tag exposing (Tag)
@@ -99,6 +108,92 @@ import Util.File
 import Util.Http as Http2
 
 
+
+--- Get Sent Mails
+
+
+getSentMails :
+    Flags
+    -> String
+    -> (Result Http.Error SentMails -> msg)
+    -> Cmd msg
+getSentMails flags item receive =
+    Http2.authGet
+        { url = flags.config.baseUrl ++ "/api/v1/sec/email/sent/item/" ++ item
+        , account = getAccount flags
+        , expect = Http.expectJson receive Api.Model.SentMails.decoder
+        }
+
+
+
+--- Mail Send
+
+
+sendMail :
+    Flags
+    -> { conn : String, item : String, mail : SimpleMail }
+    -> (Result Http.Error BasicResult -> msg)
+    -> Cmd msg
+sendMail flags opts receive =
+    Http2.authPost
+        { url = flags.config.baseUrl ++ "/api/v1/sec/email/send/" ++ opts.conn ++ "/" ++ opts.item
+        , account = getAccount flags
+        , body = Http.jsonBody (Api.Model.SimpleMail.encode opts.mail)
+        , expect = Http.expectJson receive Api.Model.BasicResult.decoder
+        }
+
+
+
+--- Mail Settings
+
+
+deleteMailSettings : Flags -> String -> (Result Http.Error BasicResult -> msg) -> Cmd msg
+deleteMailSettings flags name receive =
+    Http2.authDelete
+        { url = flags.config.baseUrl ++ "/api/v1/sec/email/settings/" ++ name
+        , account = getAccount flags
+        , expect = Http.expectJson receive Api.Model.BasicResult.decoder
+        }
+
+
+getMailSettings : Flags -> String -> (Result Http.Error EmailSettingsList -> msg) -> Cmd msg
+getMailSettings flags query receive =
+    Http2.authGet
+        { url = flags.config.baseUrl ++ "/api/v1/sec/email/settings?q=" ++ Url.percentEncode query
+        , account = getAccount flags
+        , expect = Http.expectJson receive Api.Model.EmailSettingsList.decoder
+        }
+
+
+createMailSettings :
+    Flags
+    -> Maybe String
+    -> EmailSettings
+    -> (Result Http.Error BasicResult -> msg)
+    -> Cmd msg
+createMailSettings flags mname ems receive =
+    case mname of
+        Just en ->
+            Http2.authPut
+                { url = flags.config.baseUrl ++ "/api/v1/sec/email/settings/" ++ en
+                , account = getAccount flags
+                , body = Http.jsonBody (Api.Model.EmailSettings.encode ems)
+                , expect = Http.expectJson receive Api.Model.BasicResult.decoder
+                }
+
+        Nothing ->
+            Http2.authPost
+                { url = flags.config.baseUrl ++ "/api/v1/sec/email/settings"
+                , account = getAccount flags
+                , body = Http.jsonBody (Api.Model.EmailSettings.encode ems)
+                , expect = Http.expectJson receive Api.Model.BasicResult.decoder
+                }
+
+
+
+--- Upload
+
+
 upload : Flags -> Maybe String -> ItemUploadMeta -> List File -> (String -> Result Http.Error BasicResult -> msg) -> List (Cmd msg)
 upload flags sourceId meta files receive =
     let
diff --git a/modules/webapp/src/main/elm/Comp/Dropdown.elm b/modules/webapp/src/main/elm/Comp/Dropdown.elm
index 99f44933..3ab318e9 100644
--- a/modules/webapp/src/main/elm/Comp/Dropdown.elm
+++ b/modules/webapp/src/main/elm/Comp/Dropdown.elm
@@ -395,7 +395,9 @@ viewSingle model =
                 ]
 
         renderDefault =
-            [ List.head model.selected |> Maybe.map renderClosed |> Maybe.withDefault (renderPlaceholder model)
+            [ List.head model.selected
+                |> Maybe.map renderClosed
+                |> Maybe.withDefault (renderPlaceholder model)
             , renderMenu model
             ]
 
diff --git a/modules/webapp/src/main/elm/Comp/EmailSettingsForm.elm b/modules/webapp/src/main/elm/Comp/EmailSettingsForm.elm
new file mode 100644
index 00000000..fa85576e
--- /dev/null
+++ b/modules/webapp/src/main/elm/Comp/EmailSettingsForm.elm
@@ -0,0 +1,264 @@
+module Comp.EmailSettingsForm exposing
+    ( Model
+    , Msg
+    , emptyModel
+    , getSettings
+    , init
+    , isValid
+    , update
+    , view
+    )
+
+import Api.Model.EmailSettings exposing (EmailSettings)
+import Comp.Dropdown
+import Comp.IntField
+import Comp.PasswordInput
+import Data.SSLType exposing (SSLType)
+import Html exposing (..)
+import Html.Attributes exposing (..)
+import Html.Events exposing (onCheck, onInput)
+import Util.Maybe
+
+
+type alias Model =
+    { settings : EmailSettings
+    , name : String
+    , host : String
+    , portField : Comp.IntField.Model
+    , portNum : Maybe Int
+    , user : Maybe String
+    , passField : Comp.PasswordInput.Model
+    , password : Maybe String
+    , from : String
+    , replyTo : Maybe String
+    , sslType : Comp.Dropdown.Model SSLType
+    , ignoreCertificates : Bool
+    }
+
+
+emptyModel : Model
+emptyModel =
+    { settings = Api.Model.EmailSettings.empty
+    , name = ""
+    , host = ""
+    , portField = Comp.IntField.init (Just 0) Nothing True "SMTP Port"
+    , portNum = Nothing
+    , user = Nothing
+    , passField = Comp.PasswordInput.init
+    , password = Nothing
+    , from = ""
+    , replyTo = Nothing
+    , sslType =
+        Comp.Dropdown.makeSingleList
+            { makeOption = \s -> { value = Data.SSLType.toString s, text = Data.SSLType.label s }
+            , placeholder = ""
+            , options = Data.SSLType.all
+            , selected = Just Data.SSLType.None
+            }
+    , ignoreCertificates = False
+    }
+
+
+init : EmailSettings -> Model
+init ems =
+    { settings = ems
+    , name = ems.name
+    , host = ems.smtpHost
+    , portField = Comp.IntField.init (Just 0) Nothing True "SMTP Port"
+    , portNum = ems.smtpPort
+    , user = ems.smtpUser
+    , passField = Comp.PasswordInput.init
+    , password = ems.smtpPassword
+    , from = ems.from
+    , replyTo = ems.replyTo
+    , sslType =
+        Comp.Dropdown.makeSingleList
+            { makeOption = \s -> { value = Data.SSLType.toString s, text = Data.SSLType.label s }
+            , placeholder = ""
+            , options = Data.SSLType.all
+            , selected =
+                Data.SSLType.fromString ems.sslType
+                    |> Maybe.withDefault Data.SSLType.None
+                    |> Just
+            }
+    , ignoreCertificates = ems.ignoreCertificates
+    }
+
+
+getSettings : Model -> ( Maybe String, EmailSettings )
+getSettings model =
+    ( Util.Maybe.fromString model.settings.name
+    , { name = model.name
+      , smtpHost = model.host
+      , smtpUser = model.user
+      , smtpPort = model.portNum
+      , smtpPassword = model.password
+      , from = model.from
+      , replyTo = model.replyTo
+      , sslType =
+            Comp.Dropdown.getSelected model.sslType
+                |> List.head
+                |> Maybe.withDefault Data.SSLType.None
+                |> Data.SSLType.toString
+      , ignoreCertificates = model.ignoreCertificates
+      }
+    )
+
+
+type Msg
+    = SetName String
+    | SetHost String
+    | PortMsg Comp.IntField.Msg
+    | SetUser String
+    | PassMsg Comp.PasswordInput.Msg
+    | SSLTypeMsg (Comp.Dropdown.Msg SSLType)
+    | SetFrom String
+    | SetReplyTo String
+    | ToggleCheckCert
+
+
+isValid : Model -> Bool
+isValid model =
+    model.host /= "" && model.name /= ""
+
+
+update : Msg -> Model -> ( Model, Cmd Msg )
+update msg model =
+    case msg of
+        SetName str ->
+            ( { model | name = str }, Cmd.none )
+
+        SetHost str ->
+            ( { model | host = str }, Cmd.none )
+
+        PortMsg m ->
+            let
+                ( pm, val ) =
+                    Comp.IntField.update m model.portField
+            in
+            ( { model | portField = pm, portNum = val }, Cmd.none )
+
+        SetUser str ->
+            ( { model | user = Util.Maybe.fromString str }, Cmd.none )
+
+        PassMsg m ->
+            let
+                ( pm, val ) =
+                    Comp.PasswordInput.update m model.passField
+            in
+            ( { model | passField = pm, password = val }, Cmd.none )
+
+        SSLTypeMsg m ->
+            let
+                ( sm, sc ) =
+                    Comp.Dropdown.update m model.sslType
+            in
+            ( { model | sslType = sm }, Cmd.map SSLTypeMsg sc )
+
+        SetFrom str ->
+            ( { model | from = str }, Cmd.none )
+
+        SetReplyTo str ->
+            ( { model | replyTo = Util.Maybe.fromString str }, Cmd.none )
+
+        ToggleCheckCert ->
+            ( { model | ignoreCertificates = not model.ignoreCertificates }, Cmd.none )
+
+
+view : Model -> Html Msg
+view model =
+    div
+        [ classList
+            [ ( "ui form", True )
+            , ( "error", not (isValid model) )
+            , ( "success", isValid model )
+            ]
+        ]
+        [ div [ class "required field" ]
+            [ label [] [ text "Name" ]
+            , input
+                [ type_ "text"
+                , value model.name
+                , onInput SetName
+                , placeholder "Connection name, e.g. 'gmail.com'"
+                ]
+                []
+            , div [ class "ui info message" ]
+                [ text "The connection name must not contain whitespace or special characters."
+                ]
+            ]
+        , div [ class "fields" ]
+            [ div [ class "thirteen wide required field" ]
+                [ label [] [ text "SMTP Host" ]
+                , input
+                    [ type_ "text"
+                    , placeholder "SMTP host name, e.g. 'mail.gmail.com'"
+                    , value model.host
+                    , onInput SetHost
+                    ]
+                    []
+                ]
+            , Html.map PortMsg
+                (Comp.IntField.view model.portNum
+                    "three wide field"
+                    model.portField
+                )
+            ]
+        , div [ class "two fields" ]
+            [ div [ class "field" ]
+                [ label [] [ text "SMTP User" ]
+                , input
+                    [ type_ "text"
+                    , placeholder "SMTP Username, e.g. 'your.name@gmail.com'"
+                    , Maybe.withDefault "" model.user |> value
+                    , onInput SetUser
+                    ]
+                    []
+                ]
+            , div [ class "field" ]
+                [ label [] [ text "SMTP Password" ]
+                , Html.map PassMsg (Comp.PasswordInput.view model.password model.passField)
+                ]
+            ]
+        , div [ class "two fields" ]
+            [ div [ class "required field" ]
+                [ label [] [ text "From Address" ]
+                , input
+                    [ type_ "text"
+                    , placeholder "Sender E-Mail address"
+                    , value model.from
+                    , onInput SetFrom
+                    ]
+                    []
+                ]
+            , div [ class "field" ]
+                [ label [] [ text "Reply-To" ]
+                , input
+                    [ type_ "text"
+                    , placeholder "Optional reply-to E-Mail address"
+                    , Maybe.withDefault "" model.replyTo |> value
+                    , onInput SetReplyTo
+                    ]
+                    []
+                ]
+            ]
+        , div [ class "two fields" ]
+            [ div [ class "inline field" ]
+                [ div [ class "ui checkbox" ]
+                    [ input
+                        [ type_ "checkbox"
+                        , checked model.ignoreCertificates
+                        , onCheck (\_ -> ToggleCheckCert)
+                        ]
+                        []
+                    , label [] [ text "Ignore certificate check" ]
+                    ]
+                ]
+            ]
+        , div [ class "two fields" ]
+            [ div [ class "field" ]
+                [ label [] [ text "SSL" ]
+                , Html.map SSLTypeMsg (Comp.Dropdown.view model.sslType)
+                ]
+            ]
+        ]
diff --git a/modules/webapp/src/main/elm/Comp/EmailSettingsManage.elm b/modules/webapp/src/main/elm/Comp/EmailSettingsManage.elm
new file mode 100644
index 00000000..9e3d55b8
--- /dev/null
+++ b/modules/webapp/src/main/elm/Comp/EmailSettingsManage.elm
@@ -0,0 +1,290 @@
+module Comp.EmailSettingsManage exposing
+    ( Model
+    , Msg
+    , emptyModel
+    , init
+    , update
+    , view
+    )
+
+import Api
+import Api.Model.BasicResult exposing (BasicResult)
+import Api.Model.EmailSettings exposing (EmailSettings)
+import Api.Model.EmailSettingsList exposing (EmailSettingsList)
+import Comp.EmailSettingsForm
+import Comp.EmailSettingsTable
+import Comp.YesNoDimmer
+import Data.Flags exposing (Flags)
+import Html exposing (..)
+import Html.Attributes exposing (..)
+import Html.Events exposing (onClick, onInput)
+import Http
+import Util.Http
+
+
+type alias Model =
+    { tableModel : Comp.EmailSettingsTable.Model
+    , formModel : Comp.EmailSettingsForm.Model
+    , viewMode : ViewMode
+    , formError : Maybe String
+    , loading : Bool
+    , query : String
+    , deleteConfirm : Comp.YesNoDimmer.Model
+    }
+
+
+emptyModel : Model
+emptyModel =
+    { tableModel = Comp.EmailSettingsTable.emptyModel
+    , formModel = Comp.EmailSettingsForm.emptyModel
+    , viewMode = Table
+    , formError = Nothing
+    , loading = False
+    , query = ""
+    , deleteConfirm = Comp.YesNoDimmer.emptyModel
+    }
+
+
+init : Flags -> ( Model, Cmd Msg )
+init flags =
+    ( emptyModel, Api.getMailSettings flags "" MailSettingsResp )
+
+
+type ViewMode
+    = Table
+    | Form
+
+
+type Msg
+    = TableMsg Comp.EmailSettingsTable.Msg
+    | FormMsg Comp.EmailSettingsForm.Msg
+    | SetQuery String
+    | InitNew
+    | YesNoMsg Comp.YesNoDimmer.Msg
+    | RequestDelete
+    | SetViewMode ViewMode
+    | Submit
+    | SubmitResp (Result Http.Error BasicResult)
+    | LoadSettings
+    | MailSettingsResp (Result Http.Error EmailSettingsList)
+
+
+update : Flags -> Msg -> Model -> ( Model, Cmd Msg )
+update flags msg model =
+    case msg of
+        InitNew ->
+            let
+                ems =
+                    Api.Model.EmailSettings.empty
+
+                nm =
+                    { model
+                        | viewMode = Form
+                        , formError = Nothing
+                        , formModel = Comp.EmailSettingsForm.init ems
+                    }
+            in
+            ( nm, Cmd.none )
+
+        TableMsg m ->
+            let
+                ( tm, tc ) =
+                    Comp.EmailSettingsTable.update m model.tableModel
+
+                m2 =
+                    { model
+                        | tableModel = tm
+                        , viewMode = Maybe.map (\_ -> Form) tm.selected |> Maybe.withDefault Table
+                        , formError =
+                            if tm.selected /= Nothing then
+                                Nothing
+
+                            else
+                                model.formError
+                        , formModel =
+                            case tm.selected of
+                                Just ems ->
+                                    Comp.EmailSettingsForm.init ems
+
+                                Nothing ->
+                                    model.formModel
+                    }
+            in
+            ( m2, Cmd.map TableMsg tc )
+
+        FormMsg m ->
+            let
+                ( fm, fc ) =
+                    Comp.EmailSettingsForm.update m model.formModel
+            in
+            ( { model | formModel = fm }, Cmd.map FormMsg fc )
+
+        SetQuery str ->
+            let
+                m =
+                    { model | query = str }
+            in
+            ( m, Api.getMailSettings flags str MailSettingsResp )
+
+        YesNoMsg m ->
+            let
+                ( dm, flag ) =
+                    Comp.YesNoDimmer.update m model.deleteConfirm
+
+                ( mid, _ ) =
+                    Comp.EmailSettingsForm.getSettings model.formModel
+
+                cmd =
+                    case ( flag, mid ) of
+                        ( True, Just name ) ->
+                            Api.deleteMailSettings flags name SubmitResp
+
+                        _ ->
+                            Cmd.none
+            in
+            ( { model | deleteConfirm = dm }, cmd )
+
+        RequestDelete ->
+            update flags (YesNoMsg Comp.YesNoDimmer.activate) model
+
+        SetViewMode m ->
+            ( { model | viewMode = m }, Cmd.none )
+
+        Submit ->
+            let
+                ( mid, ems ) =
+                    Comp.EmailSettingsForm.getSettings model.formModel
+
+                valid =
+                    Comp.EmailSettingsForm.isValid model.formModel
+            in
+            if valid then
+                ( { model | loading = True }, Api.createMailSettings flags mid ems SubmitResp )
+
+            else
+                ( { model | formError = Just "Please fill required fields." }, Cmd.none )
+
+        LoadSettings ->
+            ( { model | loading = True }, Api.getMailSettings flags model.query MailSettingsResp )
+
+        SubmitResp (Ok res) ->
+            if res.success then
+                let
+                    ( m2, c2 ) =
+                        update flags (SetViewMode Table) model
+
+                    ( m3, c3 ) =
+                        update flags LoadSettings m2
+                in
+                ( { m3 | loading = False }, Cmd.batch [ c2, c3 ] )
+
+            else
+                ( { model | formError = Just res.message, loading = False }, Cmd.none )
+
+        SubmitResp (Err err) ->
+            ( { model | formError = Just (Util.Http.errorToString err), loading = False }, Cmd.none )
+
+        MailSettingsResp (Ok ems) ->
+            let
+                m2 =
+                    { model
+                        | viewMode = Table
+                        , loading = False
+                        , tableModel = Comp.EmailSettingsTable.init ems.items
+                    }
+            in
+            ( m2, Cmd.none )
+
+        MailSettingsResp (Err _) ->
+            ( { model | loading = False }, Cmd.none )
+
+
+view : Model -> Html Msg
+view model =
+    case model.viewMode of
+        Table ->
+            viewTable model
+
+        Form ->
+            viewForm model
+
+
+viewTable : Model -> Html Msg
+viewTable model =
+    div []
+        [ div [ class "ui secondary menu container" ]
+            [ div [ class "ui container" ]
+                [ div [ class "fitted-item" ]
+                    [ div [ class "ui icon input" ]
+                        [ input
+                            [ type_ "text"
+                            , onInput SetQuery
+                            , value model.query
+                            , placeholder "Search…"
+                            ]
+                            []
+                        , i [ class "ui search icon" ]
+                            []
+                        ]
+                    ]
+                , div [ class "right menu" ]
+                    [ div [ class "fitted-item" ]
+                        [ a
+                            [ class "ui primary button"
+                            , href "#"
+                            , onClick InitNew
+                            ]
+                            [ i [ class "plus icon" ] []
+                            , text "New Settings"
+                            ]
+                        ]
+                    ]
+                ]
+            ]
+        , Html.map TableMsg (Comp.EmailSettingsTable.view model.tableModel)
+        ]
+
+
+viewForm : Model -> Html Msg
+viewForm model =
+    div [ class "ui segment" ]
+        [ Html.map YesNoMsg (Comp.YesNoDimmer.view model.deleteConfirm)
+        , Html.map FormMsg (Comp.EmailSettingsForm.view model.formModel)
+        , div
+            [ classList
+                [ ( "ui error message", True )
+                , ( "invisible", model.formError == Nothing )
+                ]
+            ]
+            [ Maybe.withDefault "" model.formError |> text
+            ]
+        , div [ class "ui divider" ] []
+        , button
+            [ class "ui primary button"
+            , onClick Submit
+            , href "#"
+            ]
+            [ text "Submit"
+            ]
+        , a
+            [ class "ui secondary button"
+            , onClick (SetViewMode Table)
+            , href ""
+            ]
+            [ text "Cancel"
+            ]
+        , if model.formModel.settings.name /= "" then
+            a [ class "ui right floated red button", href "", onClick RequestDelete ]
+                [ text "Delete" ]
+
+          else
+            span [] []
+        , div
+            [ classList
+                [ ( "ui dimmer", True )
+                , ( "active", model.loading )
+                ]
+            ]
+            [ div [ class "ui loader" ] []
+            ]
+        ]
diff --git a/modules/webapp/src/main/elm/Comp/EmailSettingsTable.elm b/modules/webapp/src/main/elm/Comp/EmailSettingsTable.elm
new file mode 100644
index 00000000..bfa3a388
--- /dev/null
+++ b/modules/webapp/src/main/elm/Comp/EmailSettingsTable.elm
@@ -0,0 +1,76 @@
+module Comp.EmailSettingsTable exposing
+    ( Model
+    , Msg
+    , emptyModel
+    , init
+    , update
+    , view
+    )
+
+import Api.Model.EmailSettings exposing (EmailSettings)
+import Html exposing (..)
+import Html.Attributes exposing (..)
+import Html.Events exposing (onClick)
+
+
+type alias Model =
+    { emailSettings : List EmailSettings
+    , selected : Maybe EmailSettings
+    }
+
+
+emptyModel : Model
+emptyModel =
+    init []
+
+
+init : List EmailSettings -> Model
+init ems =
+    { emailSettings = ems
+    , selected = Nothing
+    }
+
+
+type Msg
+    = Select EmailSettings
+
+
+update : Msg -> Model -> ( Model, Cmd Msg )
+update msg model =
+    case msg of
+        Select ems ->
+            ( { model | selected = Just ems }, Cmd.none )
+
+
+view : Model -> Html Msg
+view model =
+    table [ class "ui selectable pointer table" ]
+        [ thead []
+            [ th [ class "collapsible" ] [ text "Name" ]
+            , th [] [ text "Host/Port" ]
+            , th [] [ text "From" ]
+            ]
+        , tbody []
+            (List.map (renderLine model) model.emailSettings)
+        ]
+
+
+renderLine : Model -> EmailSettings -> Html Msg
+renderLine model ems =
+    let
+        hostport =
+            case ems.smtpPort of
+                Just p ->
+                    ems.smtpHost ++ ":" ++ String.fromInt p
+
+                Nothing ->
+                    ems.smtpHost
+    in
+    tr
+        [ classList [ ( "active", model.selected == Just ems ) ]
+        , onClick (Select ems)
+        ]
+        [ td [ class "collapsible" ] [ text ems.name ]
+        , td [] [ text hostport ]
+        , td [] [ text ems.from ]
+        ]
diff --git a/modules/webapp/src/main/elm/Comp/IntField.elm b/modules/webapp/src/main/elm/Comp/IntField.elm
new file mode 100644
index 00000000..498a8ec8
--- /dev/null
+++ b/modules/webapp/src/main/elm/Comp/IntField.elm
@@ -0,0 +1,114 @@
+module Comp.IntField exposing (Model, Msg, init, update, view)
+
+import Html exposing (..)
+import Html.Attributes exposing (..)
+import Html.Events exposing (onInput)
+
+
+type alias Model =
+    { min : Maybe Int
+    , max : Maybe Int
+    , label : String
+    , error : Maybe String
+    , lastInput : String
+    , optional : Bool
+    }
+
+
+type Msg
+    = SetValue String
+
+
+init : Maybe Int -> Maybe Int -> Bool -> String -> Model
+init min max opt label =
+    { min = min
+    , max = max
+    , label = label
+    , error = Nothing
+    , lastInput = ""
+    , optional = opt
+    }
+
+
+tooLow : Model -> Int -> Bool
+tooLow model n =
+    Maybe.map ((<) n) model.min
+        |> Maybe.withDefault (not model.optional)
+
+
+tooHigh : Model -> Int -> Bool
+tooHigh model n =
+    Maybe.map ((>) n) model.max
+        |> Maybe.withDefault (not model.optional)
+
+
+update : Msg -> Model -> ( Model, Maybe Int )
+update msg model =
+    let
+        tooHighError =
+            Maybe.withDefault 0 model.max
+                |> String.fromInt
+                |> (++) "Number must be <= "
+
+        tooLowError =
+            Maybe.withDefault 0 model.min
+                |> String.fromInt
+                |> (++) "Number must be >= "
+    in
+    case msg of
+        SetValue str ->
+            let
+                m =
+                    { model | lastInput = str }
+            in
+            case String.toInt str of
+                Just n ->
+                    if tooLow model n then
+                        ( { m | error = Just tooLowError }
+                        , Nothing
+                        )
+
+                    else if tooHigh model n then
+                        ( { m | error = Just tooHighError }
+                        , Nothing
+                        )
+
+                    else
+                        ( { m | error = Nothing }, Just n )
+
+                Nothing ->
+                    if model.optional && String.trim str == "" then
+                        ( { m | error = Nothing }, Nothing )
+
+                    else
+                        ( { m | error = Just ("'" ++ str ++ "' is not a valid number!") }
+                        , Nothing
+                        )
+
+
+view : Maybe Int -> String -> Model -> Html Msg
+view nval classes model =
+    div
+        [ classList
+            [ ( classes, True )
+            , ( "error", model.error /= Nothing )
+            ]
+        ]
+        [ label [] [ text model.label ]
+        , input
+            [ type_ "text"
+            , Maybe.map String.fromInt nval
+                |> Maybe.withDefault model.lastInput
+                |> value
+            , onInput SetValue
+            ]
+            []
+        , div
+            [ classList
+                [ ( "ui pointing red basic label", True )
+                , ( "hidden", model.error == Nothing )
+                ]
+            ]
+            [ Maybe.withDefault "" model.error |> text
+            ]
+        ]
diff --git a/modules/webapp/src/main/elm/Comp/ItemDetail.elm b/modules/webapp/src/main/elm/Comp/ItemDetail.elm
index 182ca64e..2559821e 100644
--- a/modules/webapp/src/main/elm/Comp/ItemDetail.elm
+++ b/modules/webapp/src/main/elm/Comp/ItemDetail.elm
@@ -17,11 +17,14 @@ import Api.Model.OptionalDate exposing (OptionalDate)
 import Api.Model.OptionalId exposing (OptionalId)
 import Api.Model.OptionalText exposing (OptionalText)
 import Api.Model.ReferenceList exposing (ReferenceList)
+import Api.Model.SentMails exposing (SentMails)
 import Api.Model.Tag exposing (Tag)
 import Api.Model.TagList exposing (TagList)
 import Browser.Navigation as Nav
 import Comp.DatePicker
 import Comp.Dropdown exposing (isDropdownChangeMsg)
+import Comp.ItemMail
+import Comp.SentMails
 import Comp.YesNoDimmer
 import Data.Direction exposing (Direction)
 import Data.Flags exposing (Flags)
@@ -32,6 +35,7 @@ import Html.Events exposing (onClick, onInput)
 import Http
 import Markdown
 import Page exposing (Page(..))
+import Util.Http
 import Util.Maybe
 import Util.Size
 import Util.String
@@ -57,6 +61,11 @@ type alias Model =
     , itemProposals : ItemProposals
     , dueDate : Maybe Int
     , dueDatePicker : DatePicker
+    , itemMail : Comp.ItemMail.Model
+    , mailOpen : Bool
+    , mailSendResult : Maybe BasicResult
+    , sentMails : Comp.SentMails.Model
+    , sentMailsOpen : Bool
     }
 
 
@@ -116,6 +125,11 @@ emptyModel =
     , itemProposals = Api.Model.ItemProposals.empty
     , dueDate = Nothing
     , dueDatePicker = Comp.DatePicker.emptyModel
+    , itemMail = Comp.ItemMail.emptyModel
+    , mailOpen = False
+    , mailSendResult = Nothing
+    , sentMails = Comp.SentMails.init
+    , sentMailsOpen = False
     }
 
 
@@ -158,6 +172,12 @@ type Msg
     | GetProposalResp (Result Http.Error ItemProposals)
     | RemoveDueDate
     | RemoveDate
+    | ItemMailMsg Comp.ItemMail.Msg
+    | ToggleMail
+    | SendMailResp (Result Http.Error BasicResult)
+    | SentMailsMsg Comp.SentMails.Msg
+    | ToggleSentMails
+    | SentMailsResp (Result Http.Error SentMails)
 
 
 
@@ -258,11 +278,7 @@ setNotes flags model =
         text =
             OptionalText model.notesModel
     in
-    if model.notesModel == Nothing then
-        Cmd.none
-
-    else
-        Api.setItemNotes flags model.item.id text SaveResp
+    Api.setItemNotes flags model.item.id text SaveResp
 
 
 setDate : Flags -> Model -> Maybe Int -> Cmd Msg
@@ -282,12 +298,17 @@ update key flags next msg model =
             let
                 ( dp, dpc ) =
                     Comp.DatePicker.init
+
+                ( im, ic ) =
+                    Comp.ItemMail.init flags
             in
-            ( { model | itemDatePicker = dp, dueDatePicker = dp }
+            ( { model | itemDatePicker = dp, dueDatePicker = dp, itemMail = im }
             , Cmd.batch
                 [ getOptions flags
                 , Cmd.map ItemDatePickerMsg dpc
                 , Cmd.map DueDatePickerMsg dpc
+                , Cmd.map ItemMailMsg ic
+                , Api.getSentMails flags model.item.id SentMailsResp
                 ]
             )
 
@@ -366,11 +387,20 @@ update key flags next msg model =
                 , itemDate = item.itemDate
                 , dueDate = item.dueDate
               }
-            , Cmd.batch [ c1, c2, c3, c4, c5, getOptions flags, proposalCmd ]
+            , Cmd.batch
+                [ c1
+                , c2
+                , c3
+                , c4
+                , c5
+                , getOptions flags
+                , proposalCmd
+                , Api.getSentMails flags item.id SentMailsResp
+                ]
             )
 
         SetActiveAttachment pos ->
-            ( { model | visibleAttach = pos }, Cmd.none )
+            ( { model | visibleAttach = pos, sentMailsOpen = False }, Cmd.none )
 
         ToggleMenu ->
             ( { model | menuOpen = not model.menuOpen }, Cmd.none )
@@ -503,14 +533,7 @@ update key flags next msg model =
             ( model, setName flags model )
 
         SetNotes str ->
-            ( { model
-                | notesModel =
-                    if str == "" then
-                        Nothing
-
-                    else
-                        Just str
-              }
+            ( { model | notesModel = Util.Maybe.fromString str }
             , Cmd.none
             )
 
@@ -690,6 +713,86 @@ update key flags next msg model =
         GetProposalResp (Err _) ->
             ( model, Cmd.none )
 
+        ItemMailMsg m ->
+            let
+                ( im, fa ) =
+                    Comp.ItemMail.update m model.itemMail
+            in
+            case fa of
+                Comp.ItemMail.FormNone ->
+                    ( { model | itemMail = im }, Cmd.none )
+
+                Comp.ItemMail.FormCancel ->
+                    ( { model
+                        | itemMail = Comp.ItemMail.clear im
+                        , mailOpen = False
+                        , mailSendResult = Nothing
+                      }
+                    , Cmd.none
+                    )
+
+                Comp.ItemMail.FormSend sm ->
+                    let
+                        mail =
+                            { item = model.item.id
+                            , mail = sm.mail
+                            , conn = sm.conn
+                            }
+                    in
+                    ( model, Api.sendMail flags mail SendMailResp )
+
+        ToggleMail ->
+            ( { model | mailOpen = not model.mailOpen }, Cmd.none )
+
+        SendMailResp (Ok br) ->
+            let
+                mm =
+                    if br.success then
+                        Comp.ItemMail.clear model.itemMail
+
+                    else
+                        model.itemMail
+            in
+            ( { model
+                | itemMail = mm
+                , mailSendResult = Just br
+              }
+            , if br.success then
+                Api.itemDetail flags model.item.id GetItemResp
+
+              else
+                Cmd.none
+            )
+
+        SendMailResp (Err err) ->
+            let
+                errmsg =
+                    Util.Http.errorToString err
+            in
+            ( { model | mailSendResult = Just (BasicResult False errmsg) }
+            , Cmd.none
+            )
+
+        SentMailsMsg m ->
+            let
+                sm =
+                    Comp.SentMails.update m model.sentMails
+            in
+            ( { model | sentMails = sm }, Cmd.none )
+
+        ToggleSentMails ->
+            ( { model | sentMailsOpen = not model.sentMailsOpen, visibleAttach = -1 }, Cmd.none )
+
+        SentMailsResp (Ok list) ->
+            let
+                sm =
+                    Comp.SentMails.initMails list.items
+            in
+            ( { model | sentMails = sm }, Cmd.none )
+
+        SentMailsResp (Err err) ->
+            ( model, Cmd.none )
+
 
 
 -- view
@@ -711,6 +814,7 @@ view inav model =
         , div
             [ classList
                 [ ( "ui ablue-comp menu", True )
+                , ( "top attached", model.mailOpen )
                 ]
             ]
             [ a [ class "item", Page.href HomePage ]
@@ -743,13 +847,25 @@ view inav model =
                     [ ( "toggle item", True )
                     , ( "active", model.menuOpen )
                     ]
-                , title "Expand Menu"
+                , title "Edit item"
                 , onClick ToggleMenu
                 , href ""
                 ]
                 [ i [ class "edit icon" ] []
                 ]
+            , a
+                [ classList
+                    [ ( "toggle item", True )
+                    , ( "active", model.mailOpen )
+                    ]
+                , title "Send Mail"
+                , onClick ToggleMail
+                , href "#"
+                ]
+                [ i [ class "mail outline icon" ] []
+                ]
             ]
+        , renderMailForm model
         , div [ class "ui grid" ]
             [ Html.map YesNoMsg (Comp.YesNoDimmer.view model.deleteConfirm)
             , div
@@ -827,7 +943,7 @@ renderNotes model =
                         , onClick ToggleNotes
                         , href "#"
                         ]
-                        [ i [ class "delete icon" ] []
+                        [ i [ class "eye slash icon" ] []
                         ]
                     ]
                 ]
@@ -835,6 +951,23 @@ renderNotes model =
 
 renderAttachmentsTabMenu : Model -> Html Msg
 renderAttachmentsTabMenu model =
+    let
+        mailTab =
+            if Comp.SentMails.isEmpty model.sentMails then
+                []
+
+            else
+                [ div
+                    [ classList
+                        [ ( "right item", True )
+                        , ( "active", model.sentMailsOpen )
+                        ]
+                    , onClick ToggleSentMails
+                    ]
+                    [ text "E-Mails"
+                    ]
+                ]
+    in
     div [ class "ui top attached tabular menu" ]
         (List.indexedMap
             (\pos ->
@@ -853,11 +986,31 @@ renderAttachmentsTabMenu model =
                         ]
             )
             model.item.attachments
+            ++ mailTab
         )
 
 
 renderAttachmentsTabBody : Model -> List (Html Msg)
 renderAttachmentsTabBody model =
+    let
+        mailTab =
+            if Comp.SentMails.isEmpty model.sentMails then
+                []
+
+            else
+                [ div
+                    [ classList
+                        [ ( "ui attached tab segment", True )
+                        , ( "active", model.sentMailsOpen )
+                        ]
+                    ]
+                    [ h3 [ class "ui header" ]
+                        [ text "Sent E-Mails"
+                        ]
+                    , Html.map SentMailsMsg (Comp.SentMails.view model.sentMails)
+                    ]
+                ]
+    in
     List.indexedMap
         (\pos ->
             \a ->
@@ -874,6 +1027,7 @@ renderAttachmentsTabBody model =
                     ]
         )
         model.item.attachments
+        ++ mailTab
 
 
 renderItemInfo : Model -> Html Msg
@@ -1197,3 +1351,37 @@ renderDueDateSuggestions model =
         Util.Time.formatDate
         (List.take 5 model.itemProposals.dueDate)
         SetDueDateSuggestion
+
+
+renderMailForm : Model -> Html Msg
+renderMailForm model =
+    div
+        [ classList
+            [ ( "ui bottom attached segment", True )
+            , ( "invisible hidden", not model.mailOpen )
+            ]
+        ]
+        [ h4 [ class "ui header" ]
+            [ text "Send this item via E-Mail"
+            ]
+        , Html.map ItemMailMsg (Comp.ItemMail.view model.itemMail)
+        , div
+            [ classList
+                [ ( "ui message", True )
+                , ( "error"
+                  , Maybe.map .success model.mailSendResult
+                        |> Maybe.map not
+                        |> Maybe.withDefault False
+                  )
+                , ( "success"
+                  , Maybe.map .success model.mailSendResult
+                        |> Maybe.withDefault False
+                  )
+                , ( "invisible hidden", model.mailSendResult == Nothing )
+                ]
+            ]
+            [ Maybe.map .message model.mailSendResult
+                |> Maybe.withDefault ""
+                |> text
+            ]
+        ]
diff --git a/modules/webapp/src/main/elm/Comp/ItemMail.elm b/modules/webapp/src/main/elm/Comp/ItemMail.elm
new file mode 100644
index 00000000..960d60ee
--- /dev/null
+++ b/modules/webapp/src/main/elm/Comp/ItemMail.elm
@@ -0,0 +1,236 @@
+module Comp.ItemMail exposing
+    ( FormAction(..)
+    , Model
+    , Msg
+    , clear
+    , emptyModel
+    , init
+    , update
+    , view
+    )
+
+import Api
+import Api.Model.EmailSettingsList exposing (EmailSettingsList)
+import Api.Model.SimpleMail exposing (SimpleMail)
+import Comp.Dropdown
+import Data.Flags exposing (Flags)
+import Html exposing (..)
+import Html.Attributes exposing (..)
+import Html.Events exposing (onCheck, onClick, onInput)
+import Http
+import Util.Http
+
+
+type alias Model =
+    { connectionModel : Comp.Dropdown.Model String
+    , subject : String
+    , receiver : String
+    , body : String
+    , attachAll : Bool
+    , formError : Maybe String
+    }
+
+
+type Msg
+    = SetSubject String
+    | SetReceiver String
+    | SetBody String
+    | ConnMsg (Comp.Dropdown.Msg String)
+    | ConnResp (Result Http.Error EmailSettingsList)
+    | ToggleAttachAll
+    | Cancel
+    | Send
+
+
+type alias MailInfo =
+    { conn : String
+    , mail : SimpleMail
+    }
+
+
+type FormAction
+    = FormSend MailInfo
+    | FormCancel
+    | FormNone
+
+
+emptyModel : Model
+emptyModel =
+    { connectionModel =
+        Comp.Dropdown.makeSingle
+            { makeOption = \a -> { value = a, text = a }
+            , placeholder = "Select connection..."
+            }
+    , subject = ""
+    , receiver = ""
+    , body = ""
+    , attachAll = True
+    , formError = Nothing
+    }
+
+
+init : Flags -> ( Model, Cmd Msg )
+init flags =
+    ( emptyModel, Api.getMailSettings flags "" ConnResp )
+
+
+clear : Model -> Model
+clear model =
+    { model
+        | subject = ""
+        , receiver = ""
+        , body = ""
+    }
+
+
+update : Msg -> Model -> ( Model, FormAction )
+update msg model =
+    case msg of
+        SetSubject str ->
+            ( { model | subject = str }, FormNone )
+
+        SetReceiver str ->
+            ( { model | receiver = str }, FormNone )
+
+        SetBody str ->
+            ( { model | body = str }, FormNone )
+
+        ConnMsg m ->
+            let
+                ( cm, _ ) =
+                    --TODO dropdown doesn't use cmd!!
+                    Comp.Dropdown.update m model.connectionModel
+            in
+            ( { model | connectionModel = cm }, FormNone )
+
+        ToggleAttachAll ->
+            ( { model | attachAll = not model.attachAll }, FormNone )
+
+        ConnResp (Ok list) ->
+            let
+                names =
+                    List.map .name list.items
+
+                cm =
+                    Comp.Dropdown.makeSingleList
+                        { makeOption = \a -> { value = a, text = a }
+                        , placeholder = "Select Connection..."
+                        , options = names
+                        , selected = List.head names
+                        }
+            in
+            ( { model
+                | connectionModel = cm
+                , formError =
+                    if names == [] then
+                        Just "No E-Mail connections configured. Goto user settings to add one."
+
+                    else
+                        Nothing
+              }
+            , FormNone
+            )
+
+        ConnResp (Err err) ->
+            ( { model | formError = Just (Util.Http.errorToString err) }, FormNone )
+
+        Cancel ->
+            ( model, FormCancel )
+
+        Send ->
+            case ( model.formError, Comp.Dropdown.getSelected model.connectionModel ) of
+                ( Nothing, conn :: [] ) ->
+                    let
+                        rec =
+                            String.split "," model.receiver
+
+                        sm =
+                            SimpleMail rec model.subject model.body model.attachAll []
+                    in
+                    ( model, FormSend { conn = conn, mail = sm } )
+
+                _ ->
+                    ( model, FormNone )
+
+
+isValid : Model -> Bool
+isValid model =
+    model.receiver
+        /= ""
+        && model.subject
+        /= ""
+        && model.body
+        /= ""
+        && model.formError
+        == Nothing
+
+
+view : Model -> Html Msg
+view model =
+    div
+        [ classList
+            [ ( "ui form", True )
+            , ( "error", model.formError /= Nothing )
+            ]
+        ]
+        [ div [ class "field" ]
+            [ label [] [ text "Send via" ]
+            , Html.map ConnMsg (Comp.Dropdown.view model.connectionModel)
+            ]
+        , div [ class "ui error message" ]
+            [ Maybe.withDefault "" model.formError |> text
+            ]
+        , div [ class "field" ]
+            [ label []
+                [ text "Receiver(s)"
+                , span [ class "muted" ]
+                    [ text "Separate multiple recipients by comma" ]
+                ]
+            , input
+                [ type_ "text"
+                , onInput SetReceiver
+                , value model.receiver
+                ]
+                []
+            ]
+        , div [ class "field" ]
+            [ label [] [ text "Subject" ]
+            , input
+                [ type_ "text"
+                , onInput SetSubject
+                , value model.subject
+                ]
+                []
+            ]
+        , div [ class "field" ]
+            [ label [] [ text "Body" ]
+            , textarea [ onInput SetBody ]
+                [ text model.body ]
+            ]
+        , div [ class "inline field" ]
+            [ div [ class "ui checkbox" ]
+                [ input
+                    [ type_ "checkbox"
+                    , checked model.attachAll
+                    , onCheck (\_ -> ToggleAttachAll)
+                    ]
+                    []
+                , label [] [ text "Include all item attachments" ]
+                ]
+            ]
+        , button
+            [ classList
+                [ ( "ui primary button", True )
+                , ( "disabled", not (isValid model) )
+                ]
+            , onClick Send
+            ]
+            [ text "Send"
+            ]
+        , button
+            [ class "ui secondary button"
+            , onClick Cancel
+            ]
+            [ text "Cancel"
+            ]
+        ]
diff --git a/modules/webapp/src/main/elm/Comp/PasswordInput.elm b/modules/webapp/src/main/elm/Comp/PasswordInput.elm
new file mode 100644
index 00000000..06f8fc94
--- /dev/null
+++ b/modules/webapp/src/main/elm/Comp/PasswordInput.elm
@@ -0,0 +1,74 @@
+module Comp.PasswordInput exposing
+    ( Model
+    , Msg
+    , init
+    , update
+    , view
+    )
+
+import Html exposing (..)
+import Html.Attributes exposing (..)
+import Html.Events exposing (onClick, onInput)
+import Util.Maybe
+
+
+type alias Model =
+    { show : Bool
+    }
+
+
+init : Model
+init =
+    { show = False
+    }
+
+
+type Msg
+    = ToggleShow (Maybe String)
+    | SetPassword String
+
+
+update : Msg -> Model -> ( Model, Maybe String )
+update msg model =
+    case msg of
+        ToggleShow pw ->
+            ( { model | show = not model.show }
+            , pw
+            )
+
+        SetPassword str ->
+            let
+                pw =
+                    Util.Maybe.fromString str
+            in
+            ( model, pw )
+
+
+view : Maybe String -> Model -> Html Msg
+view pw model =
+    div [ class "ui  left action input" ]
+        [ button
+            [ class "ui icon button"
+            , type_ "button"
+            , onClick (ToggleShow pw)
+            ]
+            [ i
+                [ classList
+                    [ ( "ui eye icon", True )
+                    , ( "slash", model.show )
+                    ]
+                ]
+                []
+            ]
+        , input
+            [ type_ <|
+                if model.show then
+                    "text"
+
+                else
+                    "password"
+            , onInput SetPassword
+            , Maybe.withDefault "" pw |> value
+            ]
+            []
+        ]
diff --git a/modules/webapp/src/main/elm/Comp/SentMails.elm b/modules/webapp/src/main/elm/Comp/SentMails.elm
new file mode 100644
index 00000000..7e4b3af0
--- /dev/null
+++ b/modules/webapp/src/main/elm/Comp/SentMails.elm
@@ -0,0 +1,121 @@
+module Comp.SentMails exposing (..)
+
+import Api.Model.SentMail exposing (SentMail)
+import Html exposing (..)
+import Html.Attributes exposing (..)
+import Html.Events exposing (onClick)
+import Util.Time
+
+
+type alias Model =
+    { mails : List SentMail
+    , selected : Maybe SentMail
+    }
+
+
+init : Model
+init =
+    { mails = []
+    , selected = Nothing
+    }
+
+
+initMails : List SentMail -> Model
+initMails mails =
+    { init | mails = mails }
+
+
+isEmpty : Model -> Bool
+isEmpty model =
+    List.isEmpty model.mails
+
+
+type Msg
+    = Show SentMail
+    | Hide
+
+
+update : Msg -> Model -> Model
+update msg model =
+    case msg of
+        Hide ->
+            { model | selected = Nothing }
+
+        Show m ->
+            { model | selected = Just m }
+
+
+view : Model -> Html Msg
+view model =
+    case model.selected of
+        Just mail ->
+            div [ class "ui blue basic segment" ]
+                [ div [ class "ui list" ]
+                    [ div [ class "item" ]
+                        [ text "From"
+                        , div [ class "header" ]
+                            [ text mail.sender
+                            , text " ("
+                            , text mail.connection
+                            , text ")"
+                            ]
+                        ]
+                    , div [ class "item" ]
+                        [ text "Date"
+                        , div [ class "header" ]
+                            [ Util.Time.formatDateTime mail.created |> text
+                            ]
+                        ]
+                    , div [ class "item" ]
+                        [ text "Recipients"
+                        , div [ class "header" ]
+                            [ String.join ", " mail.recipients |> text
+                            ]
+                        ]
+                    , div [ class "item" ]
+                        [ text "Subject"
+                        , div [ class "header" ]
+                            [ text mail.subject
+                            ]
+                        ]
+                    ]
+                , div [ class "ui horizontal divider" ] []
+                , div [ class "mail-body" ]
+                    [ text mail.body
+                    ]
+                , a
+                    [ class "ui right corner label"
+                    , onClick Hide
+                    , href "#"
+                    ]
+                    [ i [ class "close icon" ] []
+                    ]
+                ]
+
+        Nothing ->
+            table [ class "ui selectable pointer very basic table" ]
+                [ thead []
+                    [ th [ class "collapsing" ] [ text "Recipients" ]
+                    , th [] [ text "Subject" ]
+                    , th [ class "collapsible" ] [ text "Sent" ]
+                    , th [ class "collapsible" ] [ text "Sender" ]
+                    ]
+                , tbody [] <|
+                    List.map
+                        renderLine
+                        model.mails
+                ]
+
+
+renderLine : SentMail -> Html Msg
+renderLine mail =
+    tr [ onClick (Show mail) ]
+        [ td [ class "collapsing" ]
+            [ String.join ", " mail.recipients |> text
+            ]
+        , td [] [ text mail.subject ]
+        , td [ class "collapsing" ]
+            [ Util.Time.formatDateTime mail.created |> text
+            ]
+        , td [ class "collapsing" ] [ text mail.sender ]
+        ]
diff --git a/modules/webapp/src/main/elm/Data/SSLType.elm b/modules/webapp/src/main/elm/Data/SSLType.elm
new file mode 100644
index 00000000..35327f56
--- /dev/null
+++ b/modules/webapp/src/main/elm/Data/SSLType.elm
@@ -0,0 +1,60 @@
+module Data.SSLType exposing
+    ( SSLType(..)
+    , all
+    , fromString
+    , label
+    , toString
+    )
+
+
+type SSLType
+    = None
+    | SSL
+    | StartTLS
+
+
+all : List SSLType
+all =
+    [ None, SSL, StartTLS ]
+
+
+toString : SSLType -> String
+toString st =
+    case st of
+        None ->
+            "none"
+
+        SSL ->
+            "ssl"
+
+        StartTLS ->
+            "starttls"
+
+
+fromString : String -> Maybe SSLType
+fromString str =
+    case String.toLower str of
+        "none" ->
+            Just None
+
+        "ssl" ->
+            Just SSL
+
+        "starttls" ->
+            Just StartTLS
+
+        _ ->
+            Nothing
+
+
+label : SSLType -> String
+label st =
+    case st of
+        None ->
+            "None"
+
+        SSL ->
+            "SSL/TLS"
+
+        StartTLS ->
+            "StartTLS"
diff --git a/modules/webapp/src/main/elm/Page/UserSettings/Data.elm b/modules/webapp/src/main/elm/Page/UserSettings/Data.elm
index e56608a7..905c6125 100644
--- a/modules/webapp/src/main/elm/Page/UserSettings/Data.elm
+++ b/modules/webapp/src/main/elm/Page/UserSettings/Data.elm
@@ -6,11 +6,13 @@ module Page.UserSettings.Data exposing
     )
 
 import Comp.ChangePasswordForm
+import Comp.EmailSettingsManage
 
 
 type alias Model =
     { currentTab : Maybe Tab
     , changePassModel : Comp.ChangePasswordForm.Model
+    , emailSettingsModel : Comp.EmailSettingsManage.Model
     }
 
 
@@ -18,13 +20,16 @@ emptyModel : Model
 emptyModel =
     { currentTab = Nothing
     , changePassModel = Comp.ChangePasswordForm.emptyModel
+    , emailSettingsModel = Comp.EmailSettingsManage.emptyModel
     }
 
 
 type Tab
     = ChangePassTab
+    | EmailSettingsTab
 
 
 type Msg
     = SetTab Tab
     | ChangePassMsg Comp.ChangePasswordForm.Msg
+    | EmailSettingsMsg Comp.EmailSettingsManage.Msg
diff --git a/modules/webapp/src/main/elm/Page/UserSettings/Update.elm b/modules/webapp/src/main/elm/Page/UserSettings/Update.elm
index 40e34e18..8241f44c 100644
--- a/modules/webapp/src/main/elm/Page/UserSettings/Update.elm
+++ b/modules/webapp/src/main/elm/Page/UserSettings/Update.elm
@@ -1,6 +1,7 @@
 module Page.UserSettings.Update exposing (update)
 
 import Comp.ChangePasswordForm
+import Comp.EmailSettingsManage
 import Data.Flags exposing (Flags)
 import Page.UserSettings.Data exposing (..)
 
@@ -12,8 +13,20 @@ update flags msg model =
             let
                 m =
                     { model | currentTab = Just t }
+
+                ( m2, cmd ) =
+                    case t of
+                        EmailSettingsTab ->
+                            let
+                                ( em, c ) =
+                                    Comp.EmailSettingsManage.init flags
+                            in
+                            ( { m | emailSettingsModel = em }, Cmd.map EmailSettingsMsg c )
+
+                        ChangePassTab ->
+                            ( m, Cmd.none )
             in
-            ( m, Cmd.none )
+            ( m2, cmd )
 
         ChangePassMsg m ->
             let
@@ -21,3 +34,10 @@ update flags msg model =
                     Comp.ChangePasswordForm.update flags m model.changePassModel
             in
             ( { model | changePassModel = m2 }, Cmd.map ChangePassMsg c2 )
+
+        EmailSettingsMsg m ->
+            let
+                ( m2, c2 ) =
+                    Comp.EmailSettingsManage.update flags m model.emailSettingsModel
+            in
+            ( { model | emailSettingsModel = m2 }, Cmd.map EmailSettingsMsg c2 )
diff --git a/modules/webapp/src/main/elm/Page/UserSettings/View.elm b/modules/webapp/src/main/elm/Page/UserSettings/View.elm
index 6e1aee04..d89d1daa 100644
--- a/modules/webapp/src/main/elm/Page/UserSettings/View.elm
+++ b/modules/webapp/src/main/elm/Page/UserSettings/View.elm
@@ -1,6 +1,7 @@
 module Page.UserSettings.View exposing (view)
 
 import Comp.ChangePasswordForm
+import Comp.EmailSettingsManage
 import Html exposing (..)
 import Html.Attributes exposing (..)
 import Html.Events exposing (onClick)
@@ -17,13 +18,22 @@ view model =
                 ]
             , div [ class "ui attached fluid segment" ]
                 [ div [ class "ui fluid vertical secondary menu" ]
-                    [ div
+                    [ a
                         [ classActive (model.currentTab == Just ChangePassTab) "link icon item"
                         , onClick (SetTab ChangePassTab)
+                        , href "#"
                         ]
                         [ i [ class "user secret icon" ] []
                         , text "Change Password"
                         ]
+                    , a
+                        [ classActive (model.currentTab == Just EmailSettingsTab) "link icon item"
+                        , onClick (SetTab EmailSettingsTab)
+                        , href "#"
+                        ]
+                        [ i [ class "mail icon" ] []
+                        , text "E-Mail Settings"
+                        ]
                     ]
                 ]
             ]
@@ -33,6 +43,9 @@ view model =
                     Just ChangePassTab ->
                         viewChangePassword model
 
+                    Just EmailSettingsTab ->
+                        viewEmailSettings model
+
                     Nothing ->
                         []
                 )
@@ -40,6 +53,18 @@ view model =
         ]
 
 
+viewEmailSettings : Model -> List (Html Msg)
+viewEmailSettings model =
+    [ h2 [ class "ui header" ]
+        [ i [ class "mail icon" ] []
+        , div [ class "content" ]
+            [ text "E-Mail Settings"
+            ]
+        ]
+    , Html.map EmailSettingsMsg (Comp.EmailSettingsManage.view model.emailSettingsModel)
+    ]
+
+
 viewChangePassword : Model -> List (Html Msg)
 viewChangePassword model =
     [ h2 [ class "ui header" ]
diff --git a/modules/webapp/src/main/elm/Util/Maybe.elm b/modules/webapp/src/main/elm/Util/Maybe.elm
index 00de8c40..8515fdf7 100644
--- a/modules/webapp/src/main/elm/Util/Maybe.elm
+++ b/modules/webapp/src/main/elm/Util/Maybe.elm
@@ -1,5 +1,6 @@
 module Util.Maybe exposing
-    ( isEmpty
+    ( fromString
+    , isEmpty
     , nonEmpty
     , or
     , withDefault
@@ -38,3 +39,16 @@ or listma =
 
                 Nothing ->
                     or els
+
+
+fromString : String -> Maybe String
+fromString str =
+    let
+        s =
+            String.trim str
+    in
+    if s == "" then
+        Nothing
+
+    else
+        Just str
diff --git a/modules/webapp/src/main/webjar/docspell.css b/modules/webapp/src/main/webjar/docspell.css
index 24205b67..39decf23 100644
--- a/modules/webapp/src/main/webjar/docspell.css
+++ b/modules/webapp/src/main/webjar/docspell.css
@@ -65,6 +65,12 @@
     padding-right: 1em;
 }
 
+label span.muted {
+    font-size: smaller;
+    color: rgba(0,0,0,0.6);
+    margin-left: 0.5em;
+}
+
 .ui.search.dropdown.open {
     z-index: 20;
 }
@@ -88,6 +94,10 @@
     background-color: #d8dfe5;
 }
 
+.ui.selectable.pointer.table tr {
+    cursor: pointer;
+}
+
 span.small-info {
     font-size: smaller;
     color: rgba(0,0,0,0.6);
@@ -97,6 +107,10 @@ span.small-info {
     color: rgba(0,0,0,0.4);
 }
 
+.mail-body {
+    white-space: pre;
+}
+
 .login-layout, .register-layout, .newinvite-layout {
     background: #708090;
     height: 101vh;
diff --git a/project/Dependencies.scala b/project/Dependencies.scala
index 197cb751..2433e8a0 100644
--- a/project/Dependencies.scala
+++ b/project/Dependencies.scala
@@ -9,6 +9,7 @@ object Dependencies {
   val BitpeaceVersion = "0.4.2"
   val CirceVersion = "0.12.3"
   val DoobieVersion = "0.8.8"
+  val EmilVersion = "0.2.0"
   val FastparseVersion = "2.1.3"
   val FlywayVersion = "6.1.4"
   val Fs2Version = "2.1.0"
@@ -26,6 +27,11 @@ object Dependencies {
   val TikaVersion = "1.23"
   val YamuscaVersion = "0.6.1"
 
+  val emil = Seq(
+    "com.github.eikek" %% "emil-common" % EmilVersion,
+    "com.github.eikek" %% "emil-javamail" % EmilVersion    
+  )
+
   val stanfordNlpCore = Seq(
     "edu.stanford.nlp" % "stanford-corenlp" % StanfordNlpVersion excludeAll(
       ExclusionRule("com.io7m.xom", "xom"),