diff --git a/CHANGELOG.md b/CHANGELOG.md
index d9c47ceb8..654d160dc 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -22,6 +22,7 @@
 - Make the bots automatically accept group chat contact requests. #4377
 - Fetch at most 100 existing messages even if EXISTS was not received. #4383
 - jsonrpc: typescript client: fix types of events in event emitter
+- Recreate `smtp` table with AUTOINCREMENT `id`. #4390
 - delete `smtp` rows when message sending is cancelled #4391
 
 
diff --git a/src/sql/migrations.rs b/src/sql/migrations.rs
index 9493164ea..7a6e1f2a3 100644
--- a/src/sql/migrations.rs
+++ b/src/sql/migrations.rs
@@ -711,6 +711,24 @@ CREATE INDEX smtp_messageid ON imap(rfc724_mid);
         )
         .await?;
     }
+    if dbversion < 101 {
+        // Recreate `smtp` table with autoincrement.
+        // rfc724_mid index is not recreated, because it is not used.
+        sql.execute_migration(
+            "DROP TABLE smtp;
+             CREATE TABLE smtp (
+             id INTEGER PRIMARY KEY AUTOINCREMENT,
+             rfc724_mid TEXT NOT NULL,          -- Message-ID
+             mime TEXT NOT NULL,                -- SMTP payload
+             msg_id INTEGER NOT NULL,           -- ID of the message in `msgs` table
+             recipients TEXT NOT NULL,          -- List of recipients separated by space
+             retries INTEGER NOT NULL DEFAULT 0 -- Number of failed attempts to send the message
+            );
+            ",
+            101,
+        )
+        .await?;
+    }
 
     let new_version = sql
         .get_raw_config_int(VERSION_CFG)