diff --git a/src/mimefactory.rs b/src/mimefactory.rs
index bef589a25..1fb575ef4 100644
--- a/src/mimefactory.rs
+++ b/src/mimefactory.rs
@@ -852,7 +852,13 @@ impl MimeFactory {
 
         let rfc724_mid = match &self.loaded {
             Loaded::Message { msg, .. } => match &self.pre_message_mode {
-                PreMessageMode::Pre { .. } => create_outgoing_rfc724_mid(),
+                PreMessageMode::Pre { .. } => {
+                    if msg.pre_rfc724_mid.is_empty() {
+                        create_outgoing_rfc724_mid()
+                    } else {
+                        msg.pre_rfc724_mid.clone()
+                    }
+                }
                 _ => msg.rfc724_mid.clone(),
             },
             Loaded::Mdn { .. } => create_outgoing_rfc724_mid(),
diff --git a/src/test_utils.rs b/src/test_utils.rs
index f687bd3ca..8491dda86 100644
--- a/src/test_utils.rs
+++ b/src/test_utils.rs
@@ -715,7 +715,8 @@ impl TestContext {
     }
 
     pub async fn get_smtp_rows_for_msg<'a>(&'a self, msg_id: MsgId) -> Vec<SentMessage<'a>> {
-        self.ctx
+        let sent_msgs = self
+            .ctx
             .sql
             .query_map_vec(
                 "SELECT id, msg_id, mime, recipients FROM smtp WHERE msg_id=?",
@@ -737,7 +738,23 @@ impl TestContext {
                 sender_context: &self.ctx,
                 recipients,
             })
-            .collect()
+            .collect();
+        self.ctx
+            .sql
+            .execute("DELETE FROM smtp WHERE msg_id=?", (msg_id,))
+            .await
+            .expect("Delete smtp jobs");
+        update_msg_state(&self.ctx, msg_id, MessageState::OutDelivered)
+            .await
+            .expect("Update message state");
+        self.sql
+            .execute(
+                "UPDATE msgs SET timestamp_sent=? WHERE id=?",
+                (time(), msg_id),
+            )
+            .await
+            .expect("Update timestamp_sent");
+        sent_msgs
     }
 
     /// Parses a message.
diff --git a/src/tests/pre_messages/sending.rs b/src/tests/pre_messages/sending.rs
index 1d04a4a4d..063711230 100644
--- a/src/tests/pre_messages/sending.rs
+++ b/src/tests/pre_messages/sending.rs
@@ -56,23 +56,27 @@ async fn test_sending_pre_message() -> Result<()> {
             .is_some()
     );
 
+    let post_rfc724_mid = post_message_parsed
+        .headers
+        .get_header_value(HeaderDef::MessageId);
     assert_eq!(
-        post_message_parsed
-            .headers
-            .get_header_value(HeaderDef::MessageId),
+        post_rfc724_mid,
         Some(format!("<{}>", msg.rfc724_mid)),
         "Post-Message should have the rfc message id of the database message"
     );
 
+    let pre_rfc724_mid = pre_message_parsed
+        .headers
+        .get_header_value(HeaderDef::MessageId);
     assert_ne!(
-        pre_message_parsed
-            .headers
-            .get_header_value(HeaderDef::MessageId),
-        post_message_parsed
-            .headers
-            .get_header_value(HeaderDef::MessageId),
+        pre_rfc724_mid, post_rfc724_mid,
         "message ids of Pre-Message and Post-Message should be different"
     );
+    assert_eq!(
+        pre_rfc724_mid,
+        Some(format!("<{}>", msg.pre_rfc724_mid)),
+        "Unexpected pre-message RFC 724 ID"
+    );
 
     let decrypted_post_message = bob.parse_msg(post_message).await;
     assert_eq!(decrypted_post_message.decrypting_failed, false);
@@ -86,9 +90,7 @@ async fn test_sending_pre_message() -> Result<()> {
         decrypted_pre_message
             .get_header(HeaderDef::ChatPostMessageId)
             .map(String::from),
-        post_message_parsed
-            .headers
-            .get_header_value(HeaderDef::MessageId)
+        post_rfc724_mid,
     );
     assert!(
         pre_message_parsed
@@ -98,6 +100,25 @@ async fn test_sending_pre_message() -> Result<()> {
         "no Chat-Post-Message-ID header in unprotected headers of Pre-Message"
     );
 
+    chat::resend_msgs(alice, &[msg_id]).await?;
+    let smtp_rows = alice.get_smtp_rows_for_msg(msg_id).await;
+    assert_eq!(smtp_rows.len(), 2);
+
+    let pre_message_parsed = mailparse::parse_mail(smtp_rows[0].payload.as_bytes())?;
+    assert_eq!(
+        pre_message_parsed
+            .headers
+            .get_header_value(HeaderDef::MessageId),
+        pre_rfc724_mid
+    );
+    let post_message_parsed = mailparse::parse_mail(smtp_rows[1].payload.as_bytes())?;
+    assert_eq!(
+        post_message_parsed
+            .headers
+            .get_header_value(HeaderDef::MessageId),
+        post_rfc724_mid
+    );
+
     Ok(())
 }