diff --git a/src/e2ee.rs b/src/e2ee.rs
index e6332329e..e1c8f7c23 100644
--- a/src/e2ee.rs
+++ b/src/e2ee.rs
@@ -321,6 +321,11 @@ pub async fn ensure_secret_key_exists(context: &Context) -> Result<String> {
 mod tests {
     use super::*;
 
+    use crate::chat;
+    use crate::constants::Viewtype;
+    use crate::contact::{Contact, Origin};
+    use crate::message::Message;
+    use crate::param::Param;
     use crate::test_utils::*;
 
     mod ensure_secret_key_exists {
@@ -381,4 +386,106 @@ Sent with my Delta Chat Messenger: https://delta.chat";
         let data = b"blas";
         assert_eq!(has_decrypted_pgp_armor(data), false);
     }
+
+    #[async_std::test]
+    async fn test_encrypted_no_autocrypt() -> crate::error::Result<()> {
+        let alice = TestContext::new_alice().await;
+        let bob = TestContext::new_bob().await;
+
+        let (contact_alice_id, _modified) = Contact::add_or_lookup(
+            &bob.ctx,
+            "Alice",
+            "alice@example.com",
+            Origin::ManuallyCreated,
+        )
+        .await?;
+        let (contact_bob_id, _modified) = Contact::add_or_lookup(
+            &alice.ctx,
+            "Bob",
+            "bob@example.net",
+            Origin::ManuallyCreated,
+        )
+        .await?;
+
+        let chat_alice = chat::create_by_contact_id(&alice.ctx, contact_bob_id).await?;
+        let chat_bob = chat::create_by_contact_id(&bob.ctx, contact_alice_id).await?;
+
+        // Alice sends unencrypted message to Bob
+        let mut msg = Message::new(Viewtype::Text);
+        chat::prepare_msg(&alice.ctx, chat_alice, &mut msg).await?;
+        chat::send_msg(&alice.ctx, chat_alice, &mut msg).await?;
+        let sent = alice.pop_sent_msg().await;
+
+        // Bob receives unencrypted message from Alice
+        let msg = bob.parse_msg(&sent).await;
+        assert!(!msg.was_encrypted());
+
+        // Parsing a message is enough to update peerstate
+        let peerstate_alice = Peerstate::from_addr(&bob.ctx, "alice@example.com")
+            .await?
+            .expect("no peerstate found in the database");
+        assert_eq!(peerstate_alice.prefer_encrypt, EncryptPreference::Mutual);
+
+        // Bob sends encrypted message to Alice
+        let mut msg = Message::new(Viewtype::Text);
+        chat::prepare_msg(&bob.ctx, chat_bob, &mut msg).await?;
+        chat::send_msg(&bob.ctx, chat_bob, &mut msg).await?;
+        let sent = bob.pop_sent_msg().await;
+
+        // Alice receives encrypted message from Bob
+        let msg = alice.parse_msg(&sent).await;
+        assert!(msg.was_encrypted());
+
+        let peerstate_bob = Peerstate::from_addr(&alice.ctx, "bob@example.net")
+            .await?
+            .expect("no peerstate found in the database");
+        assert_eq!(peerstate_bob.prefer_encrypt, EncryptPreference::Mutual);
+
+        // Now Alice and Bob have established keys.
+
+        // Alice sends encrypted message without Autocrypt header.
+        let mut msg = Message::new(Viewtype::Text);
+        msg.param.set_int(Param::SkipAutocrypt, 1);
+        chat::prepare_msg(&alice.ctx, chat_alice, &mut msg).await?;
+        chat::send_msg(&alice.ctx, chat_alice, &mut msg).await?;
+        let sent = alice.pop_sent_msg().await;
+
+        let msg = bob.parse_msg(&sent).await;
+        assert!(msg.was_encrypted());
+        let peerstate_alice = Peerstate::from_addr(&bob.ctx, "alice@example.com")
+            .await?
+            .expect("no peerstate found in the database");
+        assert_eq!(peerstate_alice.prefer_encrypt, EncryptPreference::Mutual);
+
+        // Alice sends plaintext message with Autocrypt header.
+        let mut msg = Message::new(Viewtype::Text);
+        msg.param.set_int(Param::ForcePlaintext, 1);
+        chat::prepare_msg(&alice.ctx, chat_alice, &mut msg).await?;
+        chat::send_msg(&alice.ctx, chat_alice, &mut msg).await?;
+        let sent = alice.pop_sent_msg().await;
+
+        let msg = bob.parse_msg(&sent).await;
+        assert!(!msg.was_encrypted());
+        let peerstate_alice = Peerstate::from_addr(&bob.ctx, "alice@example.com")
+            .await?
+            .expect("no peerstate found in the database");
+        assert_eq!(peerstate_alice.prefer_encrypt, EncryptPreference::Mutual);
+
+        // Alice sends plaintext message without Autocrypt header.
+        let mut msg = Message::new(Viewtype::Text);
+        msg.param.set_int(Param::ForcePlaintext, 1);
+        msg.param.set_int(Param::SkipAutocrypt, 1);
+        chat::prepare_msg(&alice.ctx, chat_alice, &mut msg).await?;
+        chat::send_msg(&alice.ctx, chat_alice, &mut msg).await?;
+        let sent = alice.pop_sent_msg().await;
+
+        let msg = bob.parse_msg(&sent).await;
+        assert!(!msg.was_encrypted());
+        let peerstate_alice = Peerstate::from_addr(&bob.ctx, "alice@example.com")
+            .await?
+            .expect("no peerstate found in the database");
+        assert_eq!(peerstate_alice.prefer_encrypt, EncryptPreference::Reset);
+
+        Ok(())
+    }
 }