RustPython
diff --git a/‎crates/stdlib/src/ssl.rs‎
Lines changed: 8 additions & 0 deletions b/‎crates/stdlib/src/ssl.rs‎
Lines changed: 8 additions & 0 deletions
@@ -3567,6 +3567,10 @@ mod _ssl {
                         writer
                             .write_all(chunk)
                             .map_err(|e| vm.new_os_error(format!("Write failed: {e}")))?;
+                        // Flush to ensure data is converted to TLS records
+                        writer
+                            .flush()
+                            .map_err(|e| vm.new_os_error(format!("Flush failed: {e}")))?;
                     }
 
                     written = chunk_end;
@@ -3909,6 +3913,10 @@ mod _ssl {
 
             // Step 1: Send our close_notify if not already sent
             if current_state == ShutdownState::NotStarted {
+                // First, flush any pending TLS data BEFORE sending close_notify
+                // This ensures all application data is sent before the shutdown alert
+                self.flush_pending_tls_output(vm)?;
+
                 conn.send_close_notify();
 
                 // Write close_notify to outgoing buffer/BIO