diff --git a/internal/cmd/up.go b/internal/cmd/up.go
index 4648bf51..c7912f9f 100644
--- a/internal/cmd/up.go
+++ b/internal/cmd/up.go
@@ -281,6 +281,10 @@ func ensureSession(t *tmux.Tmux, sessionName, workDir, role string) error {
 		if err := t.WaitForCommand(sessionName, constants.SupportedShells, constants.ClaudeStartTimeout); err != nil {
 			// Non-fatal
 		}
+
+		// Accept bypass permissions warning dialog if it appears.
+		_ = t.AcceptBypassPermissionsWarning(sessionName)
+
 		time.Sleep(constants.ShutdownNotifyDelay)
 
 		// Inject startup nudge for predecessor discovery via /resume
@@ -330,6 +334,10 @@ func ensureWitness(t *tmux.Tmux, sessionName, rigPath, rigName string) error {
 	if err := t.WaitForCommand(sessionName, constants.SupportedShells, constants.ClaudeStartTimeout); err != nil {
 		// Non-fatal
 	}
+
+	// Accept bypass permissions warning dialog if it appears.
+	_ = t.AcceptBypassPermissionsWarning(sessionName)
+
 	time.Sleep(constants.ShutdownNotifyDelay)
 
 	// Inject startup nudge for predecessor discovery via /resume
@@ -557,6 +565,10 @@ func ensureCrewSession(t *tmux.Tmux, sessionName, crewPath, rigName, crewName st
 	if err := t.WaitForCommand(sessionName, constants.SupportedShells, constants.ClaudeStartTimeout); err != nil {
 		// Non-fatal
 	}
+
+	// Accept bypass permissions warning dialog if it appears.
+	_ = t.AcceptBypassPermissionsWarning(sessionName)
+
 	time.Sleep(constants.ShutdownNotifyDelay)
 
 	// Inject startup nudge for predecessor discovery via /resume
@@ -661,6 +673,10 @@ func ensurePolecatSession(t *tmux.Tmux, sessionName, polecatPath, rigName, polec
 	if err := t.WaitForCommand(sessionName, constants.SupportedShells, constants.ClaudeStartTimeout); err != nil {
 		// Non-fatal
 	}
+
+	// Accept bypass permissions warning dialog if it appears.
+	_ = t.AcceptBypassPermissionsWarning(sessionName)
+
 	time.Sleep(constants.ShutdownNotifyDelay)
 
 	// Inject startup nudge for predecessor discovery via /resume
diff --git a/internal/daemon/daemon.go b/internal/daemon/daemon.go
index 23c43138..49630163 100644
--- a/internal/daemon/daemon.go
+++ b/internal/daemon/daemon.go
@@ -695,6 +695,13 @@ func (d *Daemon) restartPolecatSession(rigName, polecatName, sessionName string)
 		return fmt.Errorf("sending startup command: %w", err)
 	}
 
+	// Wait for Claude to start, then accept bypass permissions warning if it appears.
+	// This ensures automated restarts aren't blocked by the warning dialog.
+	if err := d.tmux.WaitForCommand(sessionName, constants.SupportedShells, constants.ClaudeStartTimeout); err != nil {
+		// Non-fatal - Claude might still start
+	}
+	_ = d.tmux.AcceptBypassPermissionsWarning(sessionName)
+
 	return nil
 }
 
diff --git a/internal/daemon/lifecycle.go b/internal/daemon/lifecycle.go
index 2f794dd4..7f5e7bc2 100644
--- a/internal/daemon/lifecycle.go
+++ b/internal/daemon/lifecycle.go
@@ -364,6 +364,13 @@ func (d *Daemon) restartSession(sessionName, identity string) error {
 		return fmt.Errorf("sending startup command: %w", err)
 	}
 
+	// Wait for Claude to start, then accept bypass permissions warning if it appears.
+	// This ensures automated role starts aren't blocked by the warning dialog.
+	if err := d.tmux.WaitForCommand(sessionName, constants.SupportedShells, constants.ClaudeStartTimeout); err != nil {
+		// Non-fatal - Claude might still start
+	}
+	_ = d.tmux.AcceptBypassPermissionsWarning(sessionName)
+
 	// Note: gt prime is handled by Claude's SessionStart hook, not injected here.
 	// Injecting it via SendKeysDelayed causes rogue text to appear in the terminal.
 
diff --git a/internal/session/manager.go b/internal/session/manager.go
index 5b85056f..2b153581 100644
--- a/internal/session/manager.go
+++ b/internal/session/manager.go
@@ -193,12 +193,18 @@ func (m *Manager) Start(polecat string, opts StartOptions) error {
 		// Non-fatal warning - Claude might still start
 	}
 
+	// Accept bypass permissions warning dialog if it appears.
+	// When Claude starts with --dangerously-skip-permissions, it shows a warning that
+	// requires pressing Down to select "Yes, I accept" and Enter to confirm.
+	// This is needed for automated polecat startup.
+	_ = m.tmux.AcceptBypassPermissionsWarning(sessionID)
+
 	// Wait for Claude to be fully ready at the prompt (not just started)
 	// PRAGMATIC APPROACH: Use fixed delay rather than detection.
 	// WaitForClaudeReady has false positives (detects > in various contexts).
 	// Claude startup takes ~5-8 seconds on typical machines.
-	// 10 second delay is conservative but reliable.
-	time.Sleep(10 * time.Second)
+	// Reduced from 10s to 8s since AcceptBypassPermissionsWarning already adds ~1.2s.
+	time.Sleep(8 * time.Second)
 
 	// Inject startup nudge for predecessor discovery via /resume
 	// This becomes the session title in Claude Code's session picker
diff --git a/internal/tmux/tmux.go b/internal/tmux/tmux.go
index 5f2a7522..2b1a0071 100644
--- a/internal/tmux/tmux.go
+++ b/internal/tmux/tmux.go
@@ -265,6 +265,46 @@ func (t *Tmux) NudgePane(pane, message string) error {
 	return nil
 }
 
+// AcceptBypassPermissionsWarning dismisses the Claude Code bypass permissions warning dialog.
+// When Claude starts with --dangerously-skip-permissions, it shows a warning dialog that
+// requires pressing Down arrow to select "Yes, I accept" and then Enter to confirm.
+// This function checks if the warning is present before sending keys to avoid interfering
+// with sessions that don't show the warning (e.g., already accepted or different config).
+//
+// Call this after starting Claude and waiting for it to initialize (WaitForCommand),
+// but before sending any prompts.
+func (t *Tmux) AcceptBypassPermissionsWarning(session string) error {
+	// Wait for the dialog to potentially render
+	time.Sleep(1 * time.Second)
+
+	// Check if the bypass permissions warning is present
+	content, err := t.CapturePane(session, 30)
+	if err != nil {
+		return err
+	}
+
+	// Look for the characteristic warning text
+	if !strings.Contains(content, "Bypass Permissions mode") {
+		// Warning not present, nothing to do
+		return nil
+	}
+
+	// Press Down to select "Yes, I accept" (option 2)
+	if _, err := t.run("send-keys", "-t", session, "Down"); err != nil {
+		return err
+	}
+
+	// Small delay to let selection update
+	time.Sleep(200 * time.Millisecond)
+
+	// Press Enter to confirm
+	if _, err := t.run("send-keys", "-t", session, "Enter"); err != nil {
+		return err
+	}
+
+	return nil
+}
+
 // GetPaneCommand returns the current command running in a pane.
 // Returns "bash", "zsh", "claude", "node", etc.
 func (t *Tmux) GetPaneCommand(session string) (string, error) {