diff --git a/app/src/main/java/eu/faircode/email/Core.java b/app/src/main/java/eu/faircode/email/Core.java
index b3dd2a8065..244bc5f82e 100644
--- a/app/src/main/java/eu/faircode/email/Core.java
+++ b/app/src/main/java/eu/faircode/email/Core.java
@@ -584,7 +584,9 @@ class Core {
                                 EntityOperation.HEADERS.equals(op.name) ||
                                 EntityOperation.RAW.equals(op.name) ||
                                 EntityOperation.ATTACHMENT.equals(op.name) ||
-                                (EntityOperation.ADD.equals(op.name) &&
+                                ((op.tries >= LOCAL_RETRY_MAX ||
+                                        db.attachment().countAttachments(op.message) > 0) &&
+                                        EntityOperation.ADD.equals(op.name) &&
                                         EntityFolder.DRAFTS.equals(folder.type)) ||
                                 (op.tries >= LOCAL_RETRY_MAX &&
                                         EntityOperation.SYNC.equals(op.name) &&
diff --git a/app/src/main/java/eu/faircode/email/DaoAttachment.java b/app/src/main/java/eu/faircode/email/DaoAttachment.java
index 925f38b8d9..2d1b7d4d65 100644
--- a/app/src/main/java/eu/faircode/email/DaoAttachment.java
+++ b/app/src/main/java/eu/faircode/email/DaoAttachment.java
@@ -43,6 +43,10 @@ public interface DaoAttachment {
             " ORDER BY sequence, subsequence")
     List<EntityAttachment> getAttachments(long message);
 
+    @Query("SELECT COUNT(*) FROM attachment" +
+            " WHERE message = :message")
+    int countAttachments(long message);
+
     @Query("SELECT * FROM attachment" +
             " WHERE id = :id")
     EntityAttachment getAttachment(long id);