diff --git a/internal/cmd/account.go b/internal/cmd/account.go
index 17d594f8..07882b4d 100644
--- a/internal/cmd/account.go
+++ b/internal/cmd/account.go
@@ -21,8 +21,9 @@ var (
 )
 
 var accountCmd = &cobra.Command{
-	Use:   "account",
-	Short: "Manage Claude Code accounts",
+	Use:     "account",
+	GroupID: GroupConfig,
+	Short:   "Manage Claude Code accounts",
 	Long: `Manage multiple Claude Code accounts for Gas Town.
 
 This enables switching between accounts (e.g., personal vs work) with
diff --git a/internal/cmd/agents.go b/internal/cmd/agents.go
index c4757b4e..370f89a0 100644
--- a/internal/cmd/agents.go
+++ b/internal/cmd/agents.go
@@ -59,6 +59,7 @@ var AgentTypeIcons = map[AgentType]string{
 var agentsCmd = &cobra.Command{
 	Use:     "agents",
 	Aliases: []string{"ag"},
+	GroupID: GroupAgents,
 	Short:   "Switch between Gas Town agent sessions",
 	Long: `Display a popup menu of core Gas Town agent sessions.
 
diff --git a/internal/cmd/broadcast.go b/internal/cmd/broadcast.go
index 056e8e69..bfa22aeb 100644
--- a/internal/cmd/broadcast.go
+++ b/internal/cmd/broadcast.go
@@ -23,8 +23,9 @@ func init() {
 }
 
 var broadcastCmd = &cobra.Command{
-	Use:   "broadcast <message>",
-	Short: "Send a nudge message to all workers",
+	Use:     "broadcast <message>",
+	GroupID: GroupComm,
+	Short:   "Send a nudge message to all workers",
 	Long: `Broadcasts a message to all active workers (polecats and crew).
 
 By default, only workers (polecats and crew) receive the message.
diff --git a/internal/cmd/crew.go b/internal/cmd/crew.go
index 17fdfb20..687c936c 100644
--- a/internal/cmd/crew.go
+++ b/internal/cmd/crew.go
@@ -17,8 +17,9 @@ var (
 )
 
 var crewCmd = &cobra.Command{
-	Use:   "crew",
-	Short: "Manage crew workspaces (user-managed persistent workspaces)",
+	Use:     "crew",
+	GroupID: GroupWorkspace,
+	Short:   "Manage crew workspaces (user-managed persistent workspaces)",
 	Long: `Crew workers are user-managed persistent workspaces within a rig.
 
 Unlike polecats which are witness-managed and transient, crew workers are:
diff --git a/internal/cmd/daemon.go b/internal/cmd/daemon.go
index 1bc71ac9..7cdcedb3 100644
--- a/internal/cmd/daemon.go
+++ b/internal/cmd/daemon.go
@@ -14,8 +14,9 @@ import (
 )
 
 var daemonCmd = &cobra.Command{
-	Use:   "daemon",
-	Short: "Manage the Gas Town daemon",
+	Use:     "daemon",
+	GroupID: GroupServices,
+	Short:   "Manage the Gas Town daemon",
 	Long: `Manage the Gas Town background daemon.
 
 The daemon is a simple Go process that:
diff --git a/internal/cmd/deacon.go b/internal/cmd/deacon.go
index febf8fc8..8bba459f 100644
--- a/internal/cmd/deacon.go
+++ b/internal/cmd/deacon.go
@@ -21,6 +21,7 @@ const DeaconSessionName = "gt-deacon"
 var deaconCmd = &cobra.Command{
 	Use:     "deacon",
 	Aliases: []string{"dea"},
+	GroupID: GroupAgents,
 	Short:   "Manage the Deacon session",
 	Long: `Manage the Deacon tmux session.
 
@@ -156,7 +157,8 @@ func startDeaconSession(t *tmux.Tmux) error {
 	// Launch Claude directly (no shell respawn loop)
 	// Restarts are handled by daemon via ensureDeaconRunning on each heartbeat
 	// The startup hook handles context loading automatically
-	if err := t.SendKeys(DeaconSessionName, "claude --dangerously-skip-permissions"); err != nil {
+	// Export GT_ROLE in the command since tmux SetEnvironment only affects new panes
+	if err := t.SendKeys(DeaconSessionName, "export GT_ROLE=deacon && claude --dangerously-skip-permissions"); err != nil {
 		return fmt.Errorf("sending command: %w", err)
 	}
 
diff --git a/internal/cmd/doctor.go b/internal/cmd/doctor.go
index 3ae03860..a12e1898 100644
--- a/internal/cmd/doctor.go
+++ b/internal/cmd/doctor.go
@@ -16,8 +16,9 @@ var (
 )
 
 var doctorCmd = &cobra.Command{
-	Use:   "doctor",
-	Short: "Run health checks on the workspace",
+	Use:     "doctor",
+	GroupID: GroupDiag,
+	Short:   "Run health checks on the workspace",
 	Long: `Run diagnostic checks on the Gas Town workspace.
 
 Doctor checks for common configuration issues, missing files,
diff --git a/internal/cmd/done.go b/internal/cmd/done.go
index ba6c03ca..6b93b75a 100644
--- a/internal/cmd/done.go
+++ b/internal/cmd/done.go
@@ -16,8 +16,9 @@ import (
 )
 
 var doneCmd = &cobra.Command{
-	Use:   "done",
-	Short: "Signal work ready for merge queue",
+	Use:     "done",
+	GroupID: GroupWork,
+	Short:   "Signal work ready for merge queue",
 	Long: `Signal that your work is complete and ready for the merge queue.
 
 This is a convenience command for polecats that:
diff --git a/internal/cmd/down.go b/internal/cmd/down.go
index 5215ab00..ea1707a0 100644
--- a/internal/cmd/down.go
+++ b/internal/cmd/down.go
@@ -12,8 +12,9 @@ import (
 )
 
 var downCmd = &cobra.Command{
-	Use:   "down",
-	Short: "Stop all Gas Town services",
+	Use:     "down",
+	GroupID: GroupServices,
+	Short:   "Stop all Gas Town services",
 	Long: `Stop all Gas Town long-lived services.
 
 This gracefully shuts down all infrastructure agents:
diff --git a/internal/cmd/gitinit.go b/internal/cmd/gitinit.go
index bfbe7321..12bc6e29 100644
--- a/internal/cmd/gitinit.go
+++ b/internal/cmd/gitinit.go
@@ -18,8 +18,9 @@ var (
 )
 
 var gitInitCmd = &cobra.Command{
-	Use:   "git-init",
-	Short: "Initialize git repository for a Gas Town HQ",
+	Use:     "git-init",
+	GroupID: GroupWorkspace,
+	Short:   "Initialize git repository for a Gas Town HQ",
 	Long: `Initialize or configure git for an existing Gas Town HQ.
 
 This command:
diff --git a/internal/cmd/handoff.go b/internal/cmd/handoff.go
index 690f04aa..7609dc82 100644
--- a/internal/cmd/handoff.go
+++ b/internal/cmd/handoff.go
@@ -14,8 +14,9 @@ import (
 )
 
 var handoffCmd = &cobra.Command{
-	Use:   "handoff [bead-or-role]",
-	Short: "Hand off to a fresh session, work continues from hook",
+	Use:     "handoff [bead-or-role]",
+	GroupID: GroupWork,
+	Short:   "Hand off to a fresh session, work continues from hook",
 	Long: `End watch. Hand off to a fresh agent session.
 
 This is the canonical way to end any agent session. It handles all roles:
diff --git a/internal/cmd/hook.go b/internal/cmd/hook.go
index 6d6624f9..196e0a20 100644
--- a/internal/cmd/hook.go
+++ b/internal/cmd/hook.go
@@ -12,8 +12,9 @@ import (
 )
 
 var hookCmd = &cobra.Command{
-	Use:   "hook <bead-id>",
-	Short: "Attach work to your hook (durable across restarts)",
+	Use:     "hook <bead-id>",
+	GroupID: GroupWork,
+	Short:   "Attach work to your hook (durable across restarts)",
 	Long: `Attach a bead (issue) to your hook for durable work tracking.
 
 The hook is the "durability primitive" - work on your hook survives session
diff --git a/internal/cmd/hooks.go b/internal/cmd/hooks.go
index 53b44e5b..7c063ab4 100644
--- a/internal/cmd/hooks.go
+++ b/internal/cmd/hooks.go
@@ -18,8 +18,9 @@ var (
 )
 
 var hooksCmd = &cobra.Command{
-	Use:   "hooks",
-	Short: "List all Claude Code hooks in the workspace",
+	Use:     "hooks",
+	GroupID: GroupConfig,
+	Short:   "List all Claude Code hooks in the workspace",
 	Long: `List all Claude Code hooks configured in the workspace.
 
 Scans for .claude/settings.json files and displays hooks by type.
diff --git a/internal/cmd/init.go b/internal/cmd/init.go
index 02d48970..11b7961d 100644
--- a/internal/cmd/init.go
+++ b/internal/cmd/init.go
@@ -15,8 +15,9 @@ import (
 var initForce bool
 
 var initCmd = &cobra.Command{
-	Use:   "init",
-	Short: "Initialize current directory as a Gas Town rig",
+	Use:     "init",
+	GroupID: GroupWorkspace,
+	Short:   "Initialize current directory as a Gas Town rig",
 	Long: `Initialize the current directory for use as a Gas Town rig.
 
 This creates the standard agent directories (polecats/, witness/, refinery/,
diff --git a/internal/cmd/install.go b/internal/cmd/install.go
index 1af96ee7..6922f23e 100644
--- a/internal/cmd/install.go
+++ b/internal/cmd/install.go
@@ -26,8 +26,9 @@ var (
 )
 
 var installCmd = &cobra.Command{
-	Use:   "install [path]",
-	Short: "Create a new Gas Town HQ (workspace)",
+	Use:     "install [path]",
+	GroupID: GroupWorkspace,
+	Short:   "Create a new Gas Town HQ (workspace)",
 	Long: `Create a new Gas Town HQ at the specified path.
 
 The HQ (headquarters) is the top-level directory where Gas Town is installed -
diff --git a/internal/cmd/issue.go b/internal/cmd/issue.go
index e346fdc1..cfbbd39d 100644
--- a/internal/cmd/issue.go
+++ b/internal/cmd/issue.go
@@ -9,8 +9,9 @@ import (
 )
 
 var issueCmd = &cobra.Command{
-	Use:   "issue",
-	Short: "Manage current issue for status line display",
+	Use:     "issue",
+	GroupID: GroupConfig,
+	Short:   "Manage current issue for status line display",
 }
 
 var issueSetCmd = &cobra.Command{
diff --git a/internal/cmd/mail.go b/internal/cmd/mail.go
index 7936ef8d..2d0e8040 100644
--- a/internal/cmd/mail.go
+++ b/internal/cmd/mail.go
@@ -41,8 +41,9 @@ var (
 )
 
 var mailCmd = &cobra.Command{
-	Use:   "mail",
-	Short: "Agent messaging system",
+	Use:     "mail",
+	GroupID: GroupComm,
+	Short:   "Agent messaging system",
 	Long: `Send and receive messages between agents.
 
 The mail system allows Mayor, polecats, and the Refinery to communicate.
diff --git a/internal/cmd/mayor.go b/internal/cmd/mayor.go
index c0cd9ed4..5b45c863 100644
--- a/internal/cmd/mayor.go
+++ b/internal/cmd/mayor.go
@@ -17,6 +17,7 @@ const MayorSessionName = "gt-mayor"
 var mayorCmd = &cobra.Command{
 	Use:     "mayor",
 	Aliases: []string{"may"},
+	GroupID: GroupAgents,
 	Short:   "Manage the Mayor session",
 	Long: `Manage the Mayor tmux session.
 
@@ -126,7 +127,8 @@ func startMayorSession(t *tmux.Tmux) error {
 
 	// Launch Claude - the startup hook handles 'gt prime' automatically
 	// Use SendKeysDelayed to allow shell initialization after NewSession
-	claudeCmd := `claude --dangerously-skip-permissions`
+	// Export GT_ROLE in the command since tmux SetEnvironment only affects new panes
+	claudeCmd := `export GT_ROLE=mayor && claude --dangerously-skip-permissions`
 	if err := t.SendKeysDelayed(MayorSessionName, claudeCmd, 200); err != nil {
 		return fmt.Errorf("sending command: %w", err)
 	}
diff --git a/internal/cmd/molecule.go b/internal/cmd/molecule.go
index fcf9dc7d..8ebaa06a 100644
--- a/internal/cmd/molecule.go
+++ b/internal/cmd/molecule.go
@@ -21,8 +21,9 @@ var (
 )
 
 var moleculeCmd = &cobra.Command{
-	Use:     "molecule",
-	Aliases: []string{"mol"},
+	Use:     "mol",
+	Aliases: []string{"molecule"},
+	GroupID: GroupWork,
 	Short:   "Molecule workflow commands",
 	Long: `Manage molecule workflow templates.
 
diff --git a/internal/cmd/mq.go b/internal/cmd/mq.go
index cbf71bf3..f53d47ac 100644
--- a/internal/cmd/mq.go
+++ b/internal/cmd/mq.go
@@ -50,8 +50,9 @@ var (
 )
 
 var mqCmd = &cobra.Command{
-	Use:   "mq",
-	Short: "Merge queue operations",
+	Use:     "mq",
+	GroupID: GroupWork,
+	Short:   "Merge queue operations",
 	Long: `Manage the merge queue for a rig.
 
 The merge queue tracks work branches from polecats waiting to be merged.
diff --git a/internal/cmd/namepool.go b/internal/cmd/namepool.go
index 091af0c8..36017cc8 100644
--- a/internal/cmd/namepool.go
+++ b/internal/cmd/namepool.go
@@ -18,8 +18,9 @@ var (
 )
 
 var namepoolCmd = &cobra.Command{
-	Use:   "namepool",
-	Short: "Manage polecat name pools",
+	Use:     "namepool",
+	GroupID: GroupWorkspace,
+	Short:   "Manage polecat name pools",
 	Long: `Manage themed name pools for polecats in Gas Town.
 
 By default, polecats get themed names from the Mad Max universe
diff --git a/internal/cmd/nudge.go b/internal/cmd/nudge.go
index 8dce9098..49142ecf 100644
--- a/internal/cmd/nudge.go
+++ b/internal/cmd/nudge.go
@@ -14,8 +14,9 @@ func init() {
 }
 
 var nudgeCmd = &cobra.Command{
-	Use:   "nudge <rig/polecat> <message>",
-	Short: "Send a message to a polecat session reliably",
+	Use:     "nudge <rig/polecat> <message>",
+	GroupID: GroupComm,
+	Short:   "Send a message to a polecat session reliably",
 	Long: `Sends a message to a polecat's Claude Code session.
 
 Uses a reliable delivery pattern:
diff --git a/internal/cmd/orphans.go b/internal/cmd/orphans.go
index 6f77d3c6..f4041658 100644
--- a/internal/cmd/orphans.go
+++ b/internal/cmd/orphans.go
@@ -15,8 +15,9 @@ import (
 )
 
 var orphansCmd = &cobra.Command{
-	Use:   "orphans",
-	Short: "Find lost polecat work",
+	Use:     "orphans",
+	GroupID: GroupWork,
+	Short:   "Find lost polecat work",
 	Long: `Find orphaned commits that were never merged to main.
 
 Polecat work can get lost when:
diff --git a/internal/cmd/peek.go b/internal/cmd/peek.go
index 5140f496..cd15fc42 100644
--- a/internal/cmd/peek.go
+++ b/internal/cmd/peek.go
@@ -16,8 +16,9 @@ func init() {
 }
 
 var peekCmd = &cobra.Command{
-	Use:   "peek <rig/polecat> [count]",
-	Short: "View recent output from a polecat session",
+	Use:     "peek <rig/polecat> [count]",
+	GroupID: GroupComm,
+	Short:   "View recent output from a polecat session",
 	Long: `Capture and display recent terminal output from a polecat session.
 
 This is the ergonomic alias for 'gt session capture'. Use it to check
diff --git a/internal/cmd/polecat.go b/internal/cmd/polecat.go
index 7812eade..43a9a7a7 100644
--- a/internal/cmd/polecat.go
+++ b/internal/cmd/polecat.go
@@ -30,6 +30,7 @@ var (
 var polecatCmd = &cobra.Command{
 	Use:     "polecat",
 	Aliases: []string{"cat", "polecats"},
+	GroupID: GroupAgents,
 	Short:   "Manage polecats in rigs",
 	Long: `Manage polecat lifecycle in rigs.
 
diff --git a/internal/cmd/prime.go b/internal/cmd/prime.go
index f931e8ad..f9cd1f5f 100644
--- a/internal/cmd/prime.go
+++ b/internal/cmd/prime.go
@@ -33,8 +33,9 @@ const (
 )
 
 var primeCmd = &cobra.Command{
-	Use:   "prime",
-	Short: "Output role context for current directory",
+	Use:     "prime",
+	GroupID: GroupDiag,
+	Short:   "Output role context for current directory",
 	Long: `Detect the agent role from the current directory and output context.
 
 Role detection:
diff --git a/internal/cmd/refinery.go b/internal/cmd/refinery.go
index 4659b234..5ce3dcb1 100644
--- a/internal/cmd/refinery.go
+++ b/internal/cmd/refinery.go
@@ -23,6 +23,7 @@ var (
 var refineryCmd = &cobra.Command{
 	Use:     "refinery",
 	Aliases: []string{"ref"},
+	GroupID: GroupAgents,
 	Short:   "Manage the merge queue processor",
 	Long: `Manage the Refinery merge queue processor for a rig.
 
diff --git a/internal/cmd/release.go b/internal/cmd/release.go
index 30bfe06d..9fe7e12d 100644
--- a/internal/cmd/release.go
+++ b/internal/cmd/release.go
@@ -12,8 +12,9 @@ import (
 var releaseReason string
 
 var releaseCmd = &cobra.Command{
-	Use:   "release <issue-id>...",
-	Short: "Release stuck in_progress issues back to pending",
+	Use:     "release <issue-id>...",
+	GroupID: GroupWork,
+	Short:   "Release stuck in_progress issues back to pending",
 	Long: `Release one or more in_progress issues back to open/pending status.
 
 This is used to recover stuck steps when a worker dies mid-task.
diff --git a/internal/cmd/rig.go b/internal/cmd/rig.go
index 5e7c785d..701b6d71 100644
--- a/internal/cmd/rig.go
+++ b/internal/cmd/rig.go
@@ -23,8 +23,9 @@ import (
 )
 
 var rigCmd = &cobra.Command{
-	Use:   "rig",
-	Short: "Manage rigs in the workspace",
+	Use:     "rig",
+	GroupID: GroupWorkspace,
+	Short:   "Manage rigs in the workspace",
 	Long: `Manage rigs (project containers) in the Gas Town workspace.
 
 A rig is a container for managing a project and its agents:
diff --git a/internal/cmd/role.go b/internal/cmd/role.go
index 8cecc27f..a879661a 100644
--- a/internal/cmd/role.go
+++ b/internal/cmd/role.go
@@ -34,8 +34,9 @@ type RoleInfo struct {
 }
 
 var roleCmd = &cobra.Command{
-	Use:   "role",
-	Short: "Show or manage agent role",
+	Use:     "role",
+	GroupID: GroupAgents,
+	Short:   "Show or manage agent role",
 	Long: `Display the current agent role and its detection source.
 
 Role is determined by:
diff --git a/internal/cmd/root.go b/internal/cmd/root.go
index b45a47f0..52cc630f 100644
--- a/internal/cmd/root.go
+++ b/internal/cmd/root.go
@@ -32,10 +32,36 @@ func Execute() {
 	}
 }
 
+// Command group IDs - used by subcommands to organize help output
+const (
+	GroupWork      = "work"
+	GroupAgents    = "agents"
+	GroupComm      = "comm"
+	GroupServices  = "services"
+	GroupWorkspace = "workspace"
+	GroupConfig    = "config"
+	GroupDiag      = "diag"
+)
+
 func init() {
 	// Enable prefix matching for subcommands (e.g., "gt ref at" -> "gt refinery attach")
 	cobra.EnablePrefixMatching = true
 
+	// Define command groups (order determines help output order)
+	rootCmd.AddGroup(
+		&cobra.Group{ID: GroupWork, Title: "Work Management:"},
+		&cobra.Group{ID: GroupAgents, Title: "Agent Management:"},
+		&cobra.Group{ID: GroupComm, Title: "Communication:"},
+		&cobra.Group{ID: GroupServices, Title: "Services:"},
+		&cobra.Group{ID: GroupWorkspace, Title: "Workspace:"},
+		&cobra.Group{ID: GroupConfig, Title: "Configuration:"},
+		&cobra.Group{ID: GroupDiag, Title: "Diagnostics:"},
+	)
+
+	// Put help and completion in a sensible group
+	rootCmd.SetHelpCommandGroupID(GroupDiag)
+	rootCmd.SetCompletionCommandGroupID(GroupConfig)
+
 	// Global flags can be added here
 	// rootCmd.PersistentFlags().StringVar(&cfgFile, "config", "", "config file")
 }
diff --git a/internal/cmd/session.go b/internal/cmd/session.go
index 37d85870..f8f229d6 100644
--- a/internal/cmd/session.go
+++ b/internal/cmd/session.go
@@ -34,6 +34,7 @@ var (
 var sessionCmd = &cobra.Command{
 	Use:     "session",
 	Aliases: []string{"sess"},
+	GroupID: GroupAgents,
 	Short:   "Manage polecat sessions",
 	Long: `Manage tmux sessions for polecats.
 
diff --git a/internal/cmd/sling.go b/internal/cmd/sling.go
index b13f3151..7ade5c93 100644
--- a/internal/cmd/sling.go
+++ b/internal/cmd/sling.go
@@ -13,8 +13,9 @@ import (
 )
 
 var slingCmd = &cobra.Command{
-	Use:   "sling <bead-id> [target]",
-	Short: "Hook work and start immediately (no restart)",
+	Use:     "sling <bead-id> [target]",
+	GroupID: GroupWork,
+	Short:   "Hook work and start immediately (no restart)",
 	Long: `Sling work onto an agent's hook and start working immediately.
 
 Unlike 'gt handoff', sling does NOT restart the session. It:
diff --git a/internal/cmd/spawn.go b/internal/cmd/spawn.go
index a4c5420e..5c3f6bdf 100644
--- a/internal/cmd/spawn.go
+++ b/internal/cmd/spawn.go
@@ -40,6 +40,7 @@ var (
 var spawnCmd = &cobra.Command{
 	Use:     "spawn [rig/polecat | rig]",
 	Aliases: []string{"sp"},
+	GroupID: GroupWork,
 	Short:   "Spawn a polecat with work assignment",
 	Long: `Spawn a polecat with a work assignment.
 
diff --git a/internal/cmd/start.go b/internal/cmd/start.go
index ac3faded..e0c4c6f3 100644
--- a/internal/cmd/start.go
+++ b/internal/cmd/start.go
@@ -31,8 +31,9 @@ var (
 )
 
 var startCmd = &cobra.Command{
-	Use:   "start",
-	Short: "Start Gas Town",
+	Use:     "start",
+	GroupID: GroupServices,
+	Short:   "Start Gas Town",
 	Long: `Start Gas Town by launching the Deacon and Mayor.
 
 The Deacon is the health-check orchestrator that monitors Mayor and Witnesses.
@@ -46,8 +47,9 @@ To stop Gas Town, use 'gt shutdown'.`,
 }
 
 var shutdownCmd = &cobra.Command{
-	Use:   "shutdown",
-	Short: "Shutdown Gas Town",
+	Use:     "shutdown",
+	GroupID: GroupServices,
+	Short:   "Shutdown Gas Town",
 	Long: `Shutdown Gas Town by stopping agents and cleaning up polecats.
 
 By default, preserves crew sessions (your persistent workspaces).
@@ -240,7 +242,8 @@ func ensureRefinerySession(rigName string, r *rig.Rig) (bool, error) {
 	_ = t.ConfigureGasTownSession(sessionName, theme, rigName, "refinery", "refinery")
 
 	// Launch Claude in a respawn loop
-	loopCmd := `while true; do echo "🛢️ Starting Refinery for ` + rigName + `..."; claude --dangerously-skip-permissions; echo ""; echo "Refinery exited. Restarting in 2s... (Ctrl-C to stop)"; sleep 2; done`
+	// Export GT_ROLE in the command since tmux SetEnvironment only affects new panes
+	loopCmd := `export GT_ROLE=refinery && while true; do echo "🛢️ Starting Refinery for ` + rigName + `..."; claude --dangerously-skip-permissions; echo ""; echo "Refinery exited. Restarting in 2s... (Ctrl-C to stop)"; sleep 2; done`
 	if err := t.SendKeysDelayed(sessionName, loopCmd, 200); err != nil {
 		return false, fmt.Errorf("sending command: %w", err)
 	}
diff --git a/internal/cmd/status.go b/internal/cmd/status.go
index a5726164..bf4dce45 100644
--- a/internal/cmd/status.go
+++ b/internal/cmd/status.go
@@ -22,6 +22,7 @@ var statusJSON bool
 var statusCmd = &cobra.Command{
 	Use:     "status",
 	Aliases: []string{"stat"},
+	GroupID: GroupDiag,
 	Short:   "Show overall town status",
 	Long: `Display the current status of the Gas Town workspace.
 
diff --git a/internal/cmd/stop.go b/internal/cmd/stop.go
index e541d04f..95c5969a 100644
--- a/internal/cmd/stop.go
+++ b/internal/cmd/stop.go
@@ -21,8 +21,9 @@ var (
 )
 
 var stopCmd = &cobra.Command{
-	Use:   "stop",
-	Short: "Emergency stop for sessions",
+	Use:     "stop",
+	GroupID: GroupServices,
+	Short:   "Emergency stop for sessions",
 	Long: `Emergency stop command for Gas Town sessions.
 
 Stops all running polecat sessions across rigs. Use for emergency shutdown
diff --git a/internal/cmd/swarm.go b/internal/cmd/swarm.go
index 2331ba56..1d1c9325 100644
--- a/internal/cmd/swarm.go
+++ b/internal/cmd/swarm.go
@@ -34,8 +34,9 @@ var (
 )
 
 var swarmCmd = &cobra.Command{
-	Use:   "swarm",
-	Short: "Manage multi-agent swarms",
+	Use:     "swarm",
+	GroupID: GroupWork,
+	Short:   "Manage multi-agent swarms",
 	Long: `Manage coordinated multi-agent work units (swarms).
 
 A swarm coordinates multiple polecats working on related tasks from a shared
diff --git a/internal/cmd/theme.go b/internal/cmd/theme.go
index 4519aeac..998ac348 100644
--- a/internal/cmd/theme.go
+++ b/internal/cmd/theme.go
@@ -19,8 +19,9 @@ var (
 )
 
 var themeCmd = &cobra.Command{
-	Use:   "theme [name]",
-	Short: "View or set tmux theme for the current rig",
+	Use:     "theme [name]",
+	GroupID: GroupConfig,
+	Short:   "View or set tmux theme for the current rig",
 	Long: `Manage tmux status bar themes for Gas Town sessions.
 
 Without arguments, shows the current theme assignment.
diff --git a/internal/cmd/up.go b/internal/cmd/up.go
index 43c9a22f..c6700faf 100644
--- a/internal/cmd/up.go
+++ b/internal/cmd/up.go
@@ -17,8 +17,9 @@ import (
 )
 
 var upCmd = &cobra.Command{
-	Use:   "up",
-	Short: "Bring up all Gas Town services",
+	Use:     "up",
+	GroupID: GroupServices,
+	Short:   "Bring up all Gas Town services",
 	Long: `Start all Gas Town long-lived services.
 
 This is the idempotent "boot" command for Gas Town. It ensures all
@@ -213,12 +214,13 @@ func ensureSession(t *tmux.Tmux, sessionName, workDir, role string) error {
 	}
 
 	// Launch Claude
+	// Export GT_ROLE in the command since tmux SetEnvironment only affects new panes
 	var claudeCmd string
 	if role == "deacon" {
 		// Deacon uses respawn loop
-		claudeCmd = `while true; do echo "⛪ Starting Deacon session..."; claude --dangerously-skip-permissions; echo ""; echo "Deacon exited. Restarting in 2s... (Ctrl-C to stop)"; sleep 2; done`
+		claudeCmd = `export GT_ROLE=deacon && while true; do echo "⛪ Starting Deacon session..."; claude --dangerously-skip-permissions; echo ""; echo "Deacon exited. Restarting in 2s... (Ctrl-C to stop)"; sleep 2; done`
 	} else {
-		claudeCmd = `claude --dangerously-skip-permissions`
+		claudeCmd = fmt.Sprintf(`export GT_ROLE=%s && claude --dangerously-skip-permissions`, role)
 	}
 
 	if err := t.SendKeysDelayed(sessionName, claudeCmd, 200); err != nil {
@@ -252,7 +254,8 @@ func ensureWitness(t *tmux.Tmux, sessionName, rigPath, rigName string) error {
 	_ = t.ConfigureGasTownSession(sessionName, theme, "", "Witness", rigName)
 
 	// Launch Claude
-	claudeCmd := `claude --dangerously-skip-permissions`
+	// Export GT_ROLE in the command since tmux SetEnvironment only affects new panes
+	claudeCmd := `export GT_ROLE=witness && claude --dangerously-skip-permissions`
 	if err := t.SendKeysDelayed(sessionName, claudeCmd, 200); err != nil {
 		return err
 	}
diff --git a/internal/cmd/version.go b/internal/cmd/version.go
index cc745438..6635aae1 100644
--- a/internal/cmd/version.go
+++ b/internal/cmd/version.go
@@ -15,8 +15,9 @@ var (
 )
 
 var versionCmd = &cobra.Command{
-	Use:   "version",
-	Short: "Print version information",
+	Use:     "version",
+	GroupID: GroupDiag,
+	Short:   "Print version information",
 	Run: func(cmd *cobra.Command, args []string) {
 		fmt.Println(style.Bold.Render("gt") + " - Gas Town CLI")
 		fmt.Printf("Version:  %s\n", Version)
diff --git a/internal/cmd/witness.go b/internal/cmd/witness.go
index 7fd46ffe..2018d221 100644
--- a/internal/cmd/witness.go
+++ b/internal/cmd/witness.go
@@ -22,8 +22,9 @@ var (
 )
 
 var witnessCmd = &cobra.Command{
-	Use:   "witness",
-	Short: "Manage the polecat monitoring agent",
+	Use:     "witness",
+	GroupID: GroupAgents,
+	Short:   "Manage the polecat monitoring agent",
 	Long: `Manage the Witness monitoring agent for a rig.
 
 The Witness monitors polecats for stuck/idle state, nudges polecats
@@ -330,7 +331,8 @@ func ensureWitnessSession(rigName string, r *rig.Rig) (bool, error) {
 	// Launch Claude directly (no shell respawn loop)
 	// Restarts are handled by daemon via LIFECYCLE mail or deacon health-scan
 	// NOTE: No gt prime injection needed - SessionStart hook handles it automatically
-	if err := t.SendKeys(sessionName, "claude --dangerously-skip-permissions"); err != nil {
+	// Export GT_ROLE in the command since tmux SetEnvironment only affects new panes
+	if err := t.SendKeys(sessionName, "export GT_ROLE=witness && claude --dangerously-skip-permissions"); err != nil {
 		return false, fmt.Errorf("sending command: %w", err)
 	}