diff --git a/src/e2ee.rs b/src/e2ee.rs
index 63a5a7030..85d665eb4 100644
--- a/src/e2ee.rs
+++ b/src/e2ee.rs
@@ -95,6 +95,7 @@ impl EncryptHelper {
         verified: bool,
         mail_to_encrypt: lettre_email::PartBuilder,
         peerstates: Vec<(Option<Peerstate>, String)>,
+        compress: bool,
     ) -> Result<String> {
         let mut keyring: Vec<SignedPublicKey> = Vec::new();
 
@@ -135,7 +136,7 @@ impl EncryptHelper {
 
         let raw_message = mail_to_encrypt.build().as_string().into_bytes();
 
-        let ctext = pgp::pk_encrypt(&raw_message, keyring, Some(sign_key)).await?;
+        let ctext = pgp::pk_encrypt(&raw_message, keyring, Some(sign_key), compress).await?;
 
         Ok(ctext)
     }
diff --git a/src/mimefactory.rs b/src/mimefactory.rs
index 32a64b6a8..69ae0388d 100644
--- a/src/mimefactory.rs
+++ b/src/mimefactory.rs
@@ -734,8 +734,12 @@ impl<'a> MimeFactory<'a> {
                 );
             }
 
+            // Disable compression for SecureJoin to ensure
+            // there are no compression side channels
+            // leaking information about the tokens.
+            let compress = self.msg.param.get_cmd() != SystemMessage::SecurejoinMessage;
             let encrypted = encrypt_helper
-                .encrypt(context, verified, message, peerstates)
+                .encrypt(context, verified, message, peerstates, compress)
                 .await?;
 
             outer_message
diff --git a/src/pgp.rs b/src/pgp.rs
index 52ad88eab..b5791a340 100644
--- a/src/pgp.rs
+++ b/src/pgp.rs
@@ -236,6 +236,7 @@ pub async fn pk_encrypt(
     plain: &[u8],
     public_keys_for_encryption: Vec<SignedPublicKey>,
     private_key_for_signing: Option<SignedSecretKey>,
+    compress: bool,
 ) -> Result<String> {
     let lit_msg = Message::new_literal_bytes("", plain);
 
@@ -249,20 +250,19 @@ pub async fn pk_encrypt(
 
             let mut rng = thread_rng();
 
-            // TODO: measure time
             let encrypted_msg = if let Some(ref skey) = private_key_for_signing {
-                lit_msg
-                    .sign(skey, || "".into(), HASH_ALGORITHM)
-                    .and_then(|msg| msg.compress(CompressionAlgorithm::ZLIB))
-                    .and_then(|msg| {
-                        msg.encrypt_to_keys(&mut rng, SYMMETRIC_KEY_ALGORITHM, &pkeys_refs)
-                    })
+                let signed_msg = lit_msg.sign(skey, || "".into(), HASH_ALGORITHM)?;
+                let compressed_msg = if compress {
+                    signed_msg.compress(CompressionAlgorithm::ZLIB)?
+                } else {
+                    signed_msg
+                };
+                compressed_msg.encrypt_to_keys(&mut rng, SYMMETRIC_KEY_ALGORITHM, &pkeys_refs)?
             } else {
-                lit_msg.encrypt_to_keys(&mut rng, SYMMETRIC_KEY_ALGORITHM, &pkeys_refs)
+                lit_msg.encrypt_to_keys(&mut rng, SYMMETRIC_KEY_ALGORITHM, &pkeys_refs)?
             };
 
-            let msg = encrypted_msg?;
-            let encoded_msg = msg.to_armored_string(None)?;
+            let encoded_msg = encrypted_msg.to_armored_string(None)?;
 
             Ok(encoded_msg)
         })
@@ -484,10 +484,16 @@ mod tests {
         CTEXT_SIGNED
             .get_or_init(|| async {
                 let keyring = vec![KEYS.alice_public.clone(), KEYS.bob_public.clone()];
+                let compress = true;
 
-                pk_encrypt(CLEARTEXT, keyring, Some(KEYS.alice_secret.clone()))
-                    .await
-                    .unwrap()
+                pk_encrypt(
+                    CLEARTEXT,
+                    keyring,
+                    Some(KEYS.alice_secret.clone()),
+                    compress,
+                )
+                .await
+                .unwrap()
             })
             .await
     }
@@ -497,7 +503,11 @@ mod tests {
         CTEXT_UNSIGNED
             .get_or_init(|| async {
                 let keyring = vec![KEYS.alice_public.clone(), KEYS.bob_public.clone()];
-                pk_encrypt(CLEARTEXT, keyring, None).await.unwrap()
+                let compress = true;
+
+                pk_encrypt(CLEARTEXT, keyring, None, compress)
+                    .await
+                    .unwrap()
             })
             .await
     }