diff --git a/cmd/olliesrv/internal/session/session.go b/cmd/olliesrv/internal/session/session.go
index a3c9c9a..4f36e41 100644
--- a/cmd/olliesrv/internal/session/session.go
+++ b/cmd/olliesrv/internal/session/session.go
@@ -119,15 +119,23 @@ func (s *Session) ToolsConn() *toolclient.ToolsrvConn {
 // Caller is responsible for closing the returned conn.
 func (s *Session) DialToolServer() *toolclient.ToolsrvConn {
 	s.mu.RLock()
+	if s.paused {
+		s.mu.RUnlock()
+		return nil
+	}
 	k := s.Keeper
 	s.mu.RUnlock()
 	if k == nil {
+		s.log.Debug("DialToolServer: no keeper")
 		return nil
 	}
+	s.log.Debug("DialToolServer: dialing keeper paused=%v", s.IsPaused())
 	conn, err := k.Dial()
 	if err != nil {
+		s.log.Debug("DialToolServer: dial failed: %v", err)
 		return nil
 	}
+	s.log.Debug("DialToolServer: dial succeeded")
 	return conn
 }
 
@@ -351,24 +359,31 @@ func (s *Session) SetSessionID(newID string) error {
 
 // Pause stops the tool server to save resources.
 func (s *Session) Pause() error {
+	s.log.Debug("Pause: begin")
 	s.mu.Lock()
 	defer s.mu.Unlock()
 	if s.paused {
 		return fmt.Errorf("session already paused")
 	}
+	s.paused = true
+	s.log.Debug("Pause: marked paused")
 	if s.Cancel != nil {
 		s.Cancel()
 	}
+	s.log.Debug("Pause: context canceled")
 	if s.Keeper != nil {
+		s.log.Debug("Pause: closing keeper")
 		s.Keeper.Close()
 	} else if s.Proc != nil {
 		s.Proc.Close()
 	}
 	if s.toolsConn != nil {
+		s.log.Debug("Pause: closing tools connection")
 		s.toolsConn.Close()
 		s.toolsConn = nil
 	}
 	s.paused = true
+	s.log.Debug("Pause: complete")
 	go s.saveSession()
 	PublishEvent("session."+s.ID+".pause", "")
 	return nil
@@ -376,26 +391,31 @@ func (s *Session) Pause() error {
 
 // Resume restarts the tool server after a Pause.
 func (s *Session) Resume() error {
+	s.log.Debug("Resume: begin")
 	s.mu.Lock()
-	defer s.mu.Unlock()
 	if !s.paused {
+		s.mu.Unlock()
 		return fmt.Errorf("session not paused")
 	}
 
 	ctx, cancel := context.WithCancel(serverCtx)
 	s.Ctx = ctx
 	s.Cancel = cancel
+	s.log.Debug("Resume: context created")
 
 	// Ensure we always have a Keeper. If the session was restored from disk
 	// without infra, spawn a new tool server now.
 	if s.Keeper == nil {
-		cwd := ""
-		if len(s.agents) > 0 {
-			cwd = s.agents[0].Cwd()
-		}
+		s.log.Info("Resume: no keeper, starting toolsrv")
+		cwd := s.cwd
 		if cwd == "" {
 			cwd, _ = os.Getwd()
 		}
+		if s.Remote != "" {
+			s.log.Info("Resume: spawning remote toolsrv target=%s cwd=%s", s.Remote, cwd)
+		} else {
+			s.log.Info("Resume: spawning local toolsrv cwd=%s", cwd)
+		}
 		infra, err := SetupToolServer(ToolServerConfig{
 			Ctx:          ctx,
 			CWD:          cwd,
@@ -404,8 +424,12 @@ func (s *Session) Resume() error {
 			Yolo:         pkgYolo,
 		})
 		if err != nil {
+			s.log.Error("Resume: toolsrv startup failed: %v", err)
+			cancel()
+			s.mu.Unlock()
 			return fmt.Errorf("resume: %w", err)
 		}
+		s.log.Info("Resume: toolsrv started")
 		s.Proc = infra.Proc
 		s.Keeper = infra.Keeper
 		s.toolsConn = infra.ToolsConn
@@ -415,12 +439,14 @@ func (s *Session) Resume() error {
 		}
 	} else {
 		// Keeper exists — just re-dial.
+		s.log.Debug("Resume: dialing existing keeper")
 		s.Keeper.SetContext(ctx)
 		conn, err := s.Keeper.Dial()
 		if err != nil {
 			return fmt.Errorf("resume failed: %w", err)
 		}
 		s.toolsConn = conn
+		s.log.Debug("Resume: existing keeper dial succeeded")
 		// Update agent connections with fresh dials
 		for _, ag := range s.agents {
 			agConn, err := s.Keeper.Dial()
@@ -436,6 +462,13 @@ func (s *Session) Resume() error {
 	}
 
 	s.paused = false
+	s.mu.Unlock()
+	s.log.Debug("Resume: marked active")
+
+	// Start bypass approval loop for the new session context.
+	if pkgBypassNotify != nil {
+		s.StartBypassLoop(pkgBypassNotify)
+	}
 
 	// Rebuild full runtimes for restored agents (they have stub runtimes from persist).
 	for _, ag := range s.agents {
@@ -450,6 +483,7 @@ func (s *Session) Resume() error {
 	}
 	go s.saveSession()
 	PublishEvent("session."+s.ID+".resume", "")
+	s.log.Debug("Resume: complete")
 	return nil
 }