diff --git a/Changelog.md b/Changelog.md
index 7d53dd30..7f6376d5 100644
--- a/Changelog.md
+++ b/Changelog.md
@@ -4,6 +4,7 @@
 
 *Unknown*
 
+- Allow to delete attachments of an item.
 - Allow to be notified via e-mail for items with a due date. This uses
   the periodic-task framework introduced in the last release.
 - Fix issues when converting HTML with unkown links. This especially
diff --git a/modules/backend/src/main/scala/docspell/backend/ops/OItem.scala b/modules/backend/src/main/scala/docspell/backend/ops/OItem.scala
index b34e19d8..5361fb5f 100644
--- a/modules/backend/src/main/scala/docspell/backend/ops/OItem.scala
+++ b/modules/backend/src/main/scala/docspell/backend/ops/OItem.scala
@@ -66,7 +66,7 @@ trait OItem[F[_]] {
 
   def getProposals(item: Ident, collective: Ident): F[MetaProposalList]
 
-  def delete(itemId: Ident, collective: Ident): F[Int]
+  def deleteItem(itemId: Ident, collective: Ident): F[Int]
 
   def findAttachmentMeta(id: Ident, collective: Ident): F[Option[RAttachmentMeta]]
 
@@ -74,6 +74,7 @@ trait OItem[F[_]] {
 
   def findByFileSource(checksum: String, sourceId: Ident): F[Vector[RItem]]
 
+  def deleteAttachment(id: Ident, collective: Ident): F[Int]
 }
 
 object OItem {
@@ -292,7 +293,7 @@ object OItem {
           .attempt
           .map(AddResult.fromUpdate)
 
-      def delete(itemId: Ident, collective: Ident): F[Int] =
+      def deleteItem(itemId: Ident, collective: Ident): F[Int] =
         QItem.delete(store)(itemId, collective)
 
       def getProposals(item: Ident, collective: Ident): F[MetaProposalList] =
@@ -310,5 +311,7 @@ object OItem {
           items <- OptionT.liftF(QItem.findByChecksum(checksum, coll))
         } yield items).getOrElse(Vector.empty))
 
+      def deleteAttachment(id: Ident, collective: Ident): F[Int] =
+        QAttachment.deleteSingleAttachment(store)(id, collective)
     })
 }
diff --git a/modules/restapi/src/main/resources/docspell-openapi.yml b/modules/restapi/src/main/resources/docspell-openapi.yml
index 2b8e167a..13e55f73 100644
--- a/modules/restapi/src/main/resources/docspell-openapi.yml
+++ b/modules/restapi/src/main/resources/docspell-openapi.yml
@@ -1168,6 +1168,28 @@ paths:
                 $ref: "#/components/schemas/ItemProposals"
 
   /sec/attachment/{id}:
+    delete:
+      tags: [ Attachment ]
+      summary: Delete an attachment.
+      description: |
+        Deletes a single attachment with all its related data like
+        file, the original file, extracted text, results from analysis
+        etc.
+
+        If the attachment is part of an archive, the archive is only
+        deleted, if it is the last entry left. Archives are otherwise
+        not deleted, if there are remaining attachments available.
+      security:
+        - authTokenHeader: []
+      parameters:
+        - $ref: "#/components/parameters/id"
+      responses:
+        200:
+          description: Ok
+          content:
+            application/json:
+              schema:
+                $ref: "#/components/schemas/BasicResult"
     head:
       tags: [ Attachment ]
       summary: Get an attachment file.
diff --git a/modules/restserver/src/main/scala/docspell/restserver/routes/AttachmentRoutes.scala b/modules/restserver/src/main/scala/docspell/restserver/routes/AttachmentRoutes.scala
index 27fe803d..d02375a9 100644
--- a/modules/restserver/src/main/scala/docspell/restserver/routes/AttachmentRoutes.scala
+++ b/modules/restserver/src/main/scala/docspell/restserver/routes/AttachmentRoutes.scala
@@ -119,6 +119,14 @@ object AttachmentRoutes {
           md = rm.map(Conversions.mkAttachmentMeta)
           resp <- md.map(Ok(_)).getOrElse(NotFound(BasicResult(false, "Not found.")))
         } yield resp
+
+      case DELETE -> Root / Ident(id) =>
+        for {
+          n <- backend.item.deleteAttachment(id, user.account.collective)
+          res = if (n == 0) BasicResult(false, "Attachment not found")
+          else BasicResult(true, "Attachment deleted.")
+          resp <- Ok(res)
+        } yield resp
     }
   }
 
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 0bf3f5dc..881b5129 100644
--- a/modules/restserver/src/main/scala/docspell/restserver/routes/ItemRoutes.scala
+++ b/modules/restserver/src/main/scala/docspell/restserver/routes/ItemRoutes.scala
@@ -138,7 +138,7 @@ object ItemRoutes {
 
       case DELETE -> Root / Ident(id) =>
         for {
-          n <- backend.item.delete(id, user.account.collective)
+          n <- backend.item.deleteItem(id, user.account.collective)
           res = BasicResult(n > 0, if (n > 0) "Item deleted" else "Item deletion failed.")
           resp <- Ok(res)
         } yield resp
diff --git a/modules/store/src/main/scala/docspell/store/impl/Column.scala b/modules/store/src/main/scala/docspell/store/impl/Column.scala
index a42a09a3..5f47a4db 100644
--- a/modules/store/src/main/scala/docspell/store/impl/Column.scala
+++ b/modules/store/src/main/scala/docspell/store/impl/Column.scala
@@ -30,6 +30,9 @@ case class Column(name: String, ns: String = "", alias: String = "") {
   def is(c: Column): Fragment =
     f ++ fr"=" ++ c.f
 
+  def isSubquery(sq: Fragment): Fragment =
+    f ++ fr"=" ++ fr"(" ++ sq ++ fr")"
+
   def isNot[A: Put](value: A): Fragment =
     f ++ fr"<> $value"
 
diff --git a/modules/store/src/main/scala/docspell/store/queries/QAttachment.scala b/modules/store/src/main/scala/docspell/store/queries/QAttachment.scala
index e95a2acf..9f4a78b3 100644
--- a/modules/store/src/main/scala/docspell/store/queries/QAttachment.scala
+++ b/modules/store/src/main/scala/docspell/store/queries/QAttachment.scala
@@ -15,28 +15,39 @@ import docspell.common.syntax.all._
 object QAttachment {
   private[this] val logger = org.log4s.getLogger
 
-  def deleteById[F[_]: Sync](store: Store[F])(attachId: Ident, coll: Ident): F[Int] =
+  /** Deletes an attachment, its related source and meta data records.
+    * It will only delete an related archive file, if this is the last
+    * attachment in that archive.
+    */
+  def deleteSingleAttachment[F[_]: Sync](
+      store: Store[F]
+  )(attachId: Ident, coll: Ident): F[Int] = {
+    val loadFiles = for {
+      ra <- RAttachment.findByIdAndCollective(attachId, coll).map(_.map(_.fileId))
+      rs <- RAttachmentSource.findByIdAndCollective(attachId, coll).map(_.map(_.fileId))
+      ne <- RAttachmentArchive.countEntries(attachId)
+    } yield (ra, rs, ne)
+
     for {
-      raFile <- store
-        .transact(RAttachment.findByIdAndCollective(attachId, coll))
-        .map(_.map(_.fileId))
-      rsFile <- store
-        .transact(RAttachmentSource.findByIdAndCollective(attachId, coll))
-        .map(_.map(_.fileId))
-      aaFile <- store
-        .transact(RAttachmentArchive.findByIdAndCollective(attachId, coll))
-        .map(_.map(_.fileId))
+      files <- store.transact(loadFiles)
+      k <- if (files._3 == 1) deleteArchive(store)(attachId)
+      else store.transact(RAttachmentArchive.delete(attachId))
       n <- store.transact(RAttachment.delete(attachId))
       f <- Stream
-        .emits(raFile.toSeq ++ rsFile.toSeq ++ aaFile.toSeq)
+        .emits(files._1.toSeq ++ files._2.toSeq)
         .map(_.id)
         .flatMap(store.bitpeace.delete)
         .map(flag => if (flag) 1 else 0)
         .compile
         .foldMonoid
-    } yield n + f
+    } yield n + k + f
+  }
 
-  def deleteAttachment[F[_]: Sync](store: Store[F])(ra: RAttachment): F[Int] =
+  /** This deletes the attachment and *all* its related files. This used
+    * when deleting an item and should not be used to delete a
+    * *single* attachment where the item should stay.
+    */
+  private def deleteAttachment[F[_]: Sync](store: Store[F])(ra: RAttachment): F[Int] =
     for {
       _ <- logger.fdebug[F](s"Deleting attachment: ${ra.id.id}")
       s <- store.transact(RAttachmentSource.findById(ra.id))
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 8272e1d6..d79fa439 100644
--- a/modules/store/src/main/scala/docspell/store/records/RAttachment.scala
+++ b/modules/store/src/main/scala/docspell/store/records/RAttachment.scala
@@ -124,6 +124,8 @@ object RAttachment {
     q.query[(RAttachment, FileMeta)].to[Vector]
   }
 
+  /** Deletes the attachment and its related source and meta records.
+    */
   def delete(attachId: Ident): ConnectionIO[Int] =
     for {
       n0 <- RAttachmentMeta.delete(attachId)
diff --git a/modules/store/src/main/scala/docspell/store/records/RAttachmentArchive.scala b/modules/store/src/main/scala/docspell/store/records/RAttachmentArchive.scala
index b09881d7..2d1b34e0 100644
--- a/modules/store/src/main/scala/docspell/store/records/RAttachmentArchive.scala
+++ b/modules/store/src/main/scala/docspell/store/records/RAttachmentArchive.scala
@@ -91,4 +91,13 @@ object RAttachmentArchive {
       .to[Vector]
   }
 
+  /** If the given attachment id has an associated archive, this returns
+    * the number of all associated attachments. Returns 0 if there is
+    * no archive for the given attachment.
+    */
+  def countEntries(attachId: Ident): ConnectionIO[Int] = {
+    val qFileId = selectSimple(Seq(fileId), table, id.is(attachId))
+    val q       = selectCount(id, table, fileId.isSubquery(qFileId))
+    q.query[Int].unique
+  }
 }
diff --git a/modules/webapp/src/main/elm/Api.elm b/modules/webapp/src/main/elm/Api.elm
index 747944e4..ec4581ab 100644
--- a/modules/webapp/src/main/elm/Api.elm
+++ b/modules/webapp/src/main/elm/Api.elm
@@ -3,6 +3,7 @@ module Api exposing
     , changePassword
     , checkCalEvent
     , createMailSettings
+    , deleteAttachment
     , deleteEquip
     , deleteItem
     , deleteMailSettings
@@ -183,6 +184,23 @@ checkCalEvent flags input receive =
 
 
 
+--- Delete Attachment
+
+
+deleteAttachment :
+    Flags
+    -> String
+    -> (Result Http.Error BasicResult -> msg)
+    -> Cmd msg
+deleteAttachment flags attachId receive =
+    Http2.authDelete
+        { url = flags.config.baseUrl ++ "/api/v1/sec/attachment/" ++ attachId
+        , account = getAccount flags
+        , expect = Http.expectJson receive Api.Model.BasicResult.decoder
+        }
+
+
+
 --- Attachment Metadata
 
 
diff --git a/modules/webapp/src/main/elm/Comp/ItemDetail.elm b/modules/webapp/src/main/elm/Comp/ItemDetail.elm
index 8df1a9cd..57ff0a61 100644
--- a/modules/webapp/src/main/elm/Comp/ItemDetail.elm
+++ b/modules/webapp/src/main/elm/Comp/ItemDetail.elm
@@ -60,7 +60,7 @@ type alias Model =
     , nameModel : String
     , notesModel : Maybe String
     , notesField : NotesField
-    , deleteConfirm : Comp.YesNoDimmer.Model
+    , deleteItemConfirm : Comp.YesNoDimmer.Model
     , itemDatePicker : DatePicker
     , itemDate : Maybe Int
     , itemProposals : ItemProposals
@@ -75,6 +75,7 @@ type alias Model =
     , attachMeta : Dict String Comp.AttachmentMeta.Model
     , attachMetaOpen : Bool
     , pdfNativeView : Bool
+    , deleteAttachConfirm : Comp.YesNoDimmer.Model
     }
 
 
@@ -147,7 +148,7 @@ emptyModel =
     , nameModel = ""
     , notesModel = Nothing
     , notesField = ViewNotes
-    , deleteConfirm = Comp.YesNoDimmer.emptyModel
+    , deleteItemConfirm = Comp.YesNoDimmer.emptyModel
     , itemDatePicker = Comp.DatePicker.emptyModel
     , itemDate = Nothing
     , itemProposals = Api.Model.ItemProposals.empty
@@ -162,6 +163,7 @@ emptyModel =
     , attachMeta = Dict.empty
     , attachMetaOpen = False
     , pdfNativeView = False
+    , deleteAttachConfirm = Comp.YesNoDimmer.emptyModel
     }
 
 
@@ -198,7 +200,7 @@ type Msg
     | SetDueDateSuggestion Int
     | ItemDatePickerMsg Comp.DatePicker.Msg
     | DueDatePickerMsg Comp.DatePicker.Msg
-    | YesNoMsg Comp.YesNoDimmer.Msg
+    | DeleteItemConfirm Comp.YesNoDimmer.Msg
     | RequestDelete
     | SaveResp (Result Http.Error BasicResult)
     | DeleteResp (Result Http.Error BasicResult)
@@ -215,6 +217,9 @@ type Msg
     | AttachMetaClick String
     | AttachMetaMsg String Comp.AttachmentMeta.Msg
     | TogglePdfNativeView
+    | RequestDeleteAttachment String
+    | DeleteAttachConfirm String Comp.YesNoDimmer.Msg
+    | DeleteAttachResp (Result Http.Error BasicResult)
 
 
 
@@ -676,10 +681,10 @@ update key flags next msg model =
         RemoveDueDate ->
             ( { model | dueDate = Nothing }, setDueDate flags model Nothing )
 
-        YesNoMsg m ->
+        DeleteItemConfirm m ->
             let
                 ( cm, confirmed ) =
-                    Comp.YesNoDimmer.update m model.deleteConfirm
+                    Comp.YesNoDimmer.update m model.deleteItemConfirm
 
                 cmd =
                     if confirmed then
@@ -688,10 +693,10 @@ update key flags next msg model =
                     else
                         Cmd.none
             in
-            ( { model | deleteConfirm = cm }, cmd )
+            ( { model | deleteItemConfirm = cm }, cmd )
 
         RequestDelete ->
-            update key flags next (YesNoMsg Comp.YesNoDimmer.activate) model
+            update key flags next (DeleteItemConfirm Comp.YesNoDimmer.activate) model
 
         SetCorrOrgSuggestion idname ->
             ( model, setCorrOrg flags model (Just idname) )
@@ -943,6 +948,37 @@ update key flags next msg model =
             , Cmd.none
             )
 
+        DeleteAttachConfirm attachId lmsg ->
+            let
+                ( cm, confirmed ) =
+                    Comp.YesNoDimmer.update lmsg model.deleteAttachConfirm
+
+                cmd =
+                    if confirmed then
+                        Api.deleteAttachment flags attachId DeleteAttachResp
+
+                    else
+                        Cmd.none
+            in
+            ( { model | deleteAttachConfirm = cm }, cmd )
+
+        DeleteAttachResp (Ok res) ->
+            if res.success then
+                update key flags next ReloadItem model
+
+            else
+                ( model, Cmd.none )
+
+        DeleteAttachResp (Err _) ->
+            ( model, Cmd.none )
+
+        RequestDeleteAttachment id ->
+            update key
+                flags
+                next
+                (DeleteAttachConfirm id Comp.YesNoDimmer.activate)
+                model
+
 
 
 -- view
@@ -1017,7 +1053,7 @@ view inav model =
             ]
         , renderMailForm model
         , div [ class "ui grid" ]
-            [ Html.map YesNoMsg (Comp.YesNoDimmer.view model.deleteConfirm)
+            [ Html.map DeleteItemConfirm (Comp.YesNoDimmer.view model.deleteItemConfirm)
             , div
                 [ classList
                     [ ( "four wide column", True )
@@ -1206,7 +1242,8 @@ renderAttachmentView model pos attach =
             , ( "active", attachmentVisible model pos )
             ]
         ]
-        [ div [ class "ui small secondary menu" ]
+        [ Html.map (DeleteAttachConfirm attach.id) (Comp.YesNoDimmer.view model.deleteAttachConfirm)
+        , div [ class "ui small secondary menu" ]
             [ div [ class "horizontally fitted item" ]
                 [ i [ class "file outline icon" ] []
                 , text attachName
@@ -1227,6 +1264,16 @@ renderAttachmentView model pos attach =
                 ]
             , div [ class "right menu" ]
                 [ a
+                    [ classList
+                        [ ( "item", True )
+                        ]
+                    , title "Delete this file permanently"
+                    , href "#"
+                    , onClick (RequestDeleteAttachment attach.id)
+                    ]
+                    [ i [ class "red trash icon" ] []
+                    ]
+                , a
                     [ classList
                         [ ( "item", True )
                         , ( "invisible", not hasArchive )