diff --git a/internal/cmd/handoff.go b/internal/cmd/handoff.go
index e4cecc39..bfcdaa71 100644
--- a/internal/cmd/handoff.go
+++ b/internal/cmd/handoff.go
@@ -33,13 +33,17 @@ Any molecule on the hook will be auto-continued by the new session.`,
 }
 
 var (
-	handoffWatch  bool
-	handoffDryRun bool
+	handoffWatch   bool
+	handoffDryRun  bool
+	handoffSubject string
+	handoffMessage string
 )
 
 func init() {
 	handoffCmd.Flags().BoolVarP(&handoffWatch, "watch", "w", true, "Switch to new session (for remote handoff)")
 	handoffCmd.Flags().BoolVarP(&handoffDryRun, "dry-run", "n", false, "Show what would be done without executing")
+	handoffCmd.Flags().StringVarP(&handoffSubject, "subject", "s", "", "Subject for handoff mail (optional)")
+	handoffCmd.Flags().StringVarP(&handoffMessage, "message", "m", "", "Message body for handoff mail (optional)")
 	rootCmd.AddCommand(handoffCmd)
 }
 
@@ -83,6 +87,16 @@ func runHandoff(cmd *cobra.Command, args []string) error {
 		return handoffRemoteSession(t, targetSession, restartCmd)
 	}
 
+	// If subject/message provided, send handoff mail to self first
+	if handoffSubject != "" || handoffMessage != "" {
+		if err := sendHandoffMail(handoffSubject, handoffMessage); err != nil {
+			fmt.Printf("%s Warning: could not send handoff mail: %v\n", style.Dim.Render("⚠"), err)
+			// Continue anyway - the respawn is more important
+		} else {
+			fmt.Printf("%s Sent handoff mail\n", style.Bold.Render("📬"))
+		}
+	}
+
 	// Handing off ourselves - print feedback then respawn
 	fmt.Printf("%s Handing off %s...\n", style.Bold.Render("🤝"), currentSession)
 
@@ -239,3 +253,24 @@ func getSessionPane(sessionName string) (string, error) {
 	}
 	return lines[0], nil
 }
+
+// sendHandoffMail sends a handoff mail to self using gt mail send.
+func sendHandoffMail(subject, message string) error {
+	// Build subject with handoff prefix if not already present
+	if subject == "" {
+		subject = "🤝 HANDOFF: Session cycling"
+	} else if !strings.Contains(subject, "HANDOFF") {
+		subject = "🤝 HANDOFF: " + subject
+	}
+
+	// Default message if not provided
+	if message == "" {
+		message = "Context cycling. Check bd ready for pending work."
+	}
+
+	// Use gt mail send to self (--self flag sends to current agent identity)
+	cmd := exec.Command("gt", "mail", "send", "--self", "-s", subject, "-m", message)
+	cmd.Stdout = os.Stdout
+	cmd.Stderr = os.Stderr
+	return cmd.Run()
+}
diff --git a/internal/cmd/mail.go b/internal/cmd/mail.go
index b7e3dbfa..6249605d 100644
--- a/internal/cmd/mail.go
+++ b/internal/cmd/mail.go
@@ -25,6 +25,7 @@ var (
 	mailType          string
 	mailReplyTo       string
 	mailNotify        bool
+	mailSendSelf      bool
 	mailInboxJSON     bool
 	mailReadJSON      bool
 	mailInboxUnread   bool
@@ -109,8 +110,9 @@ Examples:
   gt mail send gastown/ -s "All hands" -m "Swarm starting" --notify
   gt mail send gastown/Toast -s "Task" -m "Fix bug" --type task --priority 1
   gt mail send gastown/Toast -s "Urgent" -m "Help!" --urgent
-  gt mail send mayor/ -s "Re: Status" -m "Done" --reply-to msg-abc123`,
-	Args: cobra.ExactArgs(1),
+  gt mail send mayor/ -s "Re: Status" -m "Done" --reply-to msg-abc123
+  gt mail send --self -s "Handoff" -m "Context for next session"`,
+	Args: cobra.MaximumNArgs(1),
 	RunE: runMailSend,
 }
 
@@ -233,6 +235,7 @@ func init() {
 	mailSendCmd.Flags().StringVar(&mailReplyTo, "reply-to", "", "Message ID this is replying to")
 	mailSendCmd.Flags().BoolVarP(&mailNotify, "notify", "n", false, "Send tmux notification to recipient")
 	mailSendCmd.Flags().BoolVar(&mailPinned, "pinned", false, "Pin message (for handoff context that persists)")
+	mailSendCmd.Flags().BoolVar(&mailSendSelf, "self", false, "Send to self (auto-detect from cwd)")
 	_ = mailSendCmd.MarkFlagRequired("subject")
 
 	// Inbox flags
@@ -273,7 +276,28 @@ func init() {
 }
 
 func runMailSend(cmd *cobra.Command, args []string) error {
-	to := args[0]
+	var to string
+
+	if mailSendSelf {
+		// Auto-detect identity from cwd
+		cwd, err := os.Getwd()
+		if err != nil {
+			return fmt.Errorf("getting current directory: %w", err)
+		}
+		townRoot, err := workspace.FindFromCwd()
+		if err != nil || townRoot == "" {
+			return fmt.Errorf("not in a Gas Town workspace")
+		}
+		ctx := detectRole(cwd, townRoot)
+		to = buildAgentIdentity(ctx)
+		if to == "" {
+			return fmt.Errorf("cannot determine identity from current directory (role: %s)", ctx.Role)
+		}
+	} else if len(args) > 0 {
+		to = args[0]
+	} else {
+		return fmt.Errorf("address required (or use --self)")
+	}
 
 	// All mail uses town beads (two-level architecture)
 	workDir, err := findMailWorkDir()