diff --git a/src/chat.rs b/src/chat.rs
index ab9810205..9d04f57b4 100644
--- a/src/chat.rs
+++ b/src/chat.rs
@@ -2895,11 +2895,26 @@ pub(crate) async fn create_send_msg_jobs(context: &Context, msg: &mut Message) -
     }
 
     if needs_encryption && !rendered_msg.is_encrypted {
-        /* unrecoverable */
-        message::set_msg_failed(
+        let addr = context.get_config(Config::ConfiguredAddr).await?;
+        let text = stock_str::unencrypted_email(
             context,
-            msg,
-            "End-to-end-encryption unavailable unexpectedly.",
+            addr.unwrap_or_default()
+                .split('@')
+                .nth(1)
+                .unwrap_or_default(),
+        )
+        .await;
+        message::set_msg_failed(context, msg, &text).await?;
+        add_info_msg_with_cmd(
+            context,
+            msg.chat_id,
+            &text,
+            SystemMessage::InvalidUnencryptedMail,
+            Some(msg.timestamp_sort),
+            msg.timestamp_sort,
+            None,
+            None,
+            None,
         )
         .await?;
         bail!(
diff --git a/src/e2ee.rs b/src/e2ee.rs
index e49804906..0779da3b8 100644
--- a/src/e2ee.rs
+++ b/src/e2ee.rs
@@ -113,6 +113,7 @@ mod tests {
     use crate::chat::send_text_msg;
     use crate::config::Config;
     use crate::message::Message;
+    use crate::mimeparser::SystemMessage;
     use crate::receive_imf::receive_imf;
     use crate::test_utils::{TestContext, TestContextManager};
 
@@ -165,6 +166,15 @@ Sent with my Delta Chat Messenger: https://delta.chat";
 
         let mut msg = Message::new_text("Hello!".to_string());
         assert!(chat::send_msg(alice, chat.id, &mut msg).await.is_err());
+        assert_eq!(
+            msg.error().unwrap(),
+            "\u{26a0}\u{fe0f} Your email provider example.org requires end-to-end encryption which is not setup yet."
+        );
+        let info_msg = alice.get_last_msg().await;
+        assert_eq!(
+            info_msg.get_info_type(),
+            SystemMessage::InvalidUnencryptedMail
+        );
 
         Ok(())
     }