diff --git a/modules/backend/src/main/scala/docspell/backend/BackendApp.scala b/modules/backend/src/main/scala/docspell/backend/BackendApp.scala
index da8958cc..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[_]] {
 
@@ -28,10 +29,11 @@ trait BackendApp[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)
@@ -46,7 +48,7 @@ object BackendApp {
       nodeImpl   <- ONode(store)
       jobImpl    <- OJob(store, httpClientEc)
       itemImpl   <- OItem(store)
-      mailImpl   <- OMail(store)
+      mailImpl   <- OMail(store, JavaMailEmil(blocker))
     } yield new BackendApp[F] {
       val login: Login[F]            = loginImpl
       val signup: OSignup[F]         = signupImpl
@@ -70,6 +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
index 6fd9ab32..80875f92 100644
--- a/modules/backend/src/main/scala/docspell/backend/ops/OMail.scala
+++ b/modules/backend/src/main/scala/docspell/backend/ops/OMail.scala
@@ -1,14 +1,22 @@
 package docspell.backend.ops
 
+import fs2.Stream
 import cats.effect._
 import cats.implicits._
 import cats.data.OptionT
-import emil.{MailAddress, SSLType}
+import emil._
+import emil.javamail.syntax._
 
 import docspell.common._
 import docspell.store._
 import docspell.store.records.RUserEmail
 import OMail.{ItemMail, SmtpSettings}
+import docspell.store.records.RAttachment
+import bitpeace.FileMeta
+import bitpeace.RangeDef
+import docspell.store.records.RItem
+import docspell.store.records.RSentMail
+import docspell.store.records.RSentMailItem
 
 trait OMail[F[_]] {
 
@@ -35,10 +43,19 @@ object OMail {
       attach: AttachSelection
   )
 
-  sealed trait AttachSelection
+  sealed trait AttachSelection {
+    def filter(v: Vector[(RAttachment, FileMeta)]): Vector[(RAttachment, FileMeta)]
+  }
   object AttachSelection {
-    case object All                       extends AttachSelection
-    case class Selected(ids: List[Ident]) extends 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(
@@ -68,7 +85,7 @@ object OMail {
       )
   }
 
-  def apply[F[_]: Effect](store: Store[F]): Resource[F, OMail[F]] =
+  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))
@@ -97,7 +114,71 @@ object OMail {
       def deleteSettings(accId: AccountId, name: Ident): F[Int] =
         store.transact(RUserEmail.delete(accId, name))
 
-      def sendMail(accId: AccountId, name: Ident, m: ItemMail): F[SendResult] =
-        Effect[F].pure(SendResult.Failure(new Exception("not implemented")))
+      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,
+              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)
+      }
+
     })
 }
diff --git a/modules/backend/src/main/scala/docspell/backend/ops/SendResult.scala b/modules/backend/src/main/scala/docspell/backend/ops/SendResult.scala
index b3ac6450..f64f48f6 100644
--- a/modules/backend/src/main/scala/docspell/backend/ops/SendResult.scala
+++ b/modules/backend/src/main/scala/docspell/backend/ops/SendResult.scala
@@ -6,7 +6,21 @@ sealed trait SendResult
 
 object SendResult {
 
+  /** Mail was successfully sent and stored to db.
+    */
   case class Success(id: Ident) extends SendResult
 
-  case class Failure(ex: Throwable) 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/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/routes/MailSendRoutes.scala b/modules/restserver/src/main/scala/docspell/restserver/routes/MailSendRoutes.scala
index 8c10c33e..3d7a08e3 100644
--- a/modules/restserver/src/main/scala/docspell/restserver/routes/MailSendRoutes.scala
+++ b/modules/restserver/src/main/scala/docspell/restserver/routes/MailSendRoutes.scala
@@ -46,7 +46,11 @@ object MailSendRoutes {
     res match {
       case SendResult.Success(_) =>
         BasicResult(true, "Mail sent.")
-      case SendResult.Failure(ex) =>
+      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/store/src/main/scala/docspell/store/impl/DoobieMeta.scala b/modules/store/src/main/scala/docspell/store/impl/DoobieMeta.scala
index 84762e0b..62f058cd 100644
--- a/modules/store/src/main/scala/docspell/store/impl/DoobieMeta.scala
+++ b/modules/store/src/main/scala/docspell/store/impl/DoobieMeta.scala
@@ -95,7 +95,9 @@ trait DoobieMeta {
     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 {
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
index 9bde3fcc..8eb1b43d 100644
--- a/modules/store/src/main/scala/docspell/store/records/RSentMail.scala
+++ b/modules/store/src/main/scala/docspell/store/records/RSentMail.scala
@@ -1,12 +1,15 @@
 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,
@@ -21,17 +24,46 @@ case class RSentMail(
 
 object RSentMail {
 
+  def apply[F[_]: Sync](
+      uid: Ident,
+      messageId: String,
+      sender: MailAddress,
+      subject: String,
+      recipients: List[MailAddress],
+      body: String
+  ): F[RSentMail] =
+    for {
+      id  <- Ident.randomId[F]
+      now <- Timestamp.current[F]
+    } yield RSentMail(id, uid, messageId, sender, subject, recipients, body, now)
+
+  def forItem(
+      itemId: Ident,
+      accId: AccountId,
+      messageId: String,
+      sender: MailAddress,
+      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, 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 subject      = Column("subject")
-    val recipients      = Column("recipients")
+    val id         = Column("id")
+    val uid        = Column("uid")
+    val messageId  = Column("message_id")
+    val sender     = Column("sender")
+    val subject    = Column("subject")
+    val recipients = Column("recipients")
     val body       = Column("body")
-    val created       = Column("created")
+    val created    = Column("created")
 
     val all = List(
       id,
diff --git a/modules/store/src/main/scala/docspell/store/records/RSentMailItem.scala b/modules/store/src/main/scala/docspell/store/records/RSentMailItem.scala
index 2a729539..b9b12da2 100644
--- a/modules/store/src/main/scala/docspell/store/records/RSentMailItem.scala
+++ b/modules/store/src/main/scala/docspell/store/records/RSentMailItem.scala
@@ -17,13 +17,16 @@ case class RSentMailItem(
 
 object RSentMailItem {
 
-  def create[F[_]: Sync](itemId: Ident, sentmailId: Ident, created: Option[Timestamp] = None): F[RSentMailItem] =
+  def apply[F[_]: Sync](
+      itemId: Ident,
+      sentmailId: Ident,
+      created: Option[Timestamp] = None
+  ): F[RSentMailItem] =
     for {
-      id <- Ident.randomId[F]
+      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 {
diff --git a/modules/store/src/main/scala/docspell/store/records/RUserEmail.scala b/modules/store/src/main/scala/docspell/store/records/RUserEmail.scala
index cc67029b..e8fcc0b7 100644
--- a/modules/store/src/main/scala/docspell/store/records/RUserEmail.scala
+++ b/modules/store/src/main/scala/docspell/store/records/RUserEmail.scala
@@ -8,7 +8,7 @@ import cats.data.OptionT
 import docspell.common._
 import docspell.store.impl.Column
 import docspell.store.impl.Implicits._
-import emil.{MailAddress, SSLType}
+import emil.{MailAddress, MailConfig, SSLType}
 
 case class RUserEmail(
     id: Ident,
@@ -23,7 +23,19 @@ case class RUserEmail(
     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 {
 
diff --git a/project/Dependencies.scala b/project/Dependencies.scala
index 33dcd904..73bb2890 100644
--- a/project/Dependencies.scala
+++ b/project/Dependencies.scala
@@ -9,7 +9,7 @@ object Dependencies {
   val BitpeaceVersion = "0.4.2"
   val CirceVersion = "0.12.3"
   val DoobieVersion = "0.8.8"
-  val EmilVersion = "0.1.1"
+  val EmilVersion = "0.1.2-SNAPSHOT"
   val FastparseVersion = "2.1.3"
   val FlywayVersion = "6.1.3"
   val Fs2Version = "2.1.0"