diff --git a/internal/client/client.go b/internal/client/client.go
index 2dfc153..541b2d5 100644
--- a/internal/client/client.go
+++ b/internal/client/client.go
@@ -388,15 +388,15 @@ func (c *Client) handleReconnect(ctx context.Context, cfg Config, cancel context
 	if oldControlStop != nil {
 		oldControlStop()
 	}
-	if oldControl != nil {
-		_ = oldControl.Close()
-	}
 	if oldSess != nil {
 		_ = oldSess.Close()
 	}
 	if oldConn != nil {
 		_ = oldConn.Close()
 	}
+	if oldControl != nil {
+		_ = oldControl.Close()
+	}
 
 	// Server-side may still be tearing down its own session when our callback
 	// fires — carriers don't guarantee reconnect callbacks are delivered to both
@@ -587,6 +587,9 @@ func (c *Client) shutdown() {
 	if controlStop != nil {
 		controlStop()
 	}
+	if sess != nil {
+		_ = sess.Close()
+	}
 	if conn != nil {
 		_ = conn.Close()
 	}
@@ -596,9 +599,6 @@ func (c *Client) shutdown() {
 	if control != nil {
 		_ = control.Close()
 	}
-	if sess != nil {
-		_ = sess.Close()
-	}
 }
 
 func setupCipher(keyHex string) (*crypto.Cipher, error) {
diff --git a/internal/server/server.go b/internal/server/server.go
index 2c28805..743c40b 100644
--- a/internal/server/server.go
+++ b/internal/server/server.go
@@ -415,12 +415,12 @@ func (s *Server) closeSession() {
 	if controlStop != nil {
 		controlStop()
 	}
-	if conn != nil {
-		_ = conn.Close()
-	}
 	if sess != nil {
 		_ = sess.Close()
 	}
+	if conn != nil {
+		_ = conn.Close()
+	}
 	if oldSID != "" {
 		s.onClose(oldSID, "closed")
 	}
diff --git a/internal/supervisor/supervisor.go b/internal/supervisor/supervisor.go
index 30b8a1f..9406952 100644
--- a/internal/supervisor/supervisor.go
+++ b/internal/supervisor/supervisor.go
@@ -98,6 +98,9 @@ func Run(ctx context.Context, cfg Config, run Runner) error {
 		if err := runCycle(ctx, cfg, run, state, cycle, &lastErr); err != nil {
 			return err
 		}
+		if ctx.Err() != nil {
+			return nil //nolint:nilerr // context cancellation is normal supervisor shutdown
+		}
 	}
 }