diff --git a/cmd/clawgo/main.go b/cmd/clawgo/main.go
index 5026c0d..0a16b9f 100644
--- a/cmd/clawgo/main.go
+++ b/cmd/clawgo/main.go
@@ -714,6 +714,7 @@ func gatewayCmd() {
 		fmt.Printf("Error initializing gateway runtime: %v\n", err)
 		os.Exit(1)
 	}
+	sentinelService.SetManager(channelManager)
 
 	pidFile := filepath.Join(filepath.Dir(getConfigPath()), "gateway.pid")
 	if err := os.WriteFile(pidFile, []byte(fmt.Sprintf("%d\n", os.Getpid())), 0644); err != nil {
@@ -797,6 +798,7 @@ func gatewayCmd() {
 					},
 				)
 				if newCfg.Sentinel.Enabled {
+					sentinelService.SetManager(channelManager)
 					sentinelService.Start()
 				}
 				cfg = newCfg
@@ -835,6 +837,7 @@ func gatewayCmd() {
 			if newCfg.Sentinel.Enabled {
 				sentinelService.Start()
 			}
+			sentinelService.SetManager(channelManager)
 
 			if err := channelManager.StartAll(ctx); err != nil {
 				fmt.Printf("✗ Reload failed (start channels): %v\n", err)
diff --git a/pkg/agent/loop.go b/pkg/agent/loop.go
index 58f1363..15ce279 100644
--- a/pkg/agent/loop.go
+++ b/pkg/agent/loop.go
@@ -82,8 +82,9 @@ func NewAgentLoop(cfg *config.Config, msgBus *bus.MessageBus, provider providers
 
 	// Register message tool
 	messageTool := tools.NewMessageTool()
-	messageTool.SetSendCallback(func(channel, chatID, content string) error {
+	messageTool.SetSendCallback(func(channel, chatID, content string, buttons [][]bus.Button) error {
 		msgBus.PublishOutbound(bus.OutboundMessage{
+			Buttons: buttons,
 			Channel: channel,
 			ChatID:  chatID,
 			Content: content,
@@ -210,6 +211,7 @@ func (al *AgentLoop) enqueueMessage(ctx context.Context, msg bus.InboundMessage)
 	case <-ctx.Done():
 	case <-time.After(2 * time.Second):
 		al.bus.PublishOutbound(bus.OutboundMessage{
+			Buttons: buttons,
 			Channel: msg.Channel,
 			ChatID:  msg.ChatID,
 			Content: "Message queue is busy. Please try again shortly.",
@@ -275,6 +277,7 @@ func (al *AgentLoop) runSessionWorker(ctx context.Context, sessionKey string, wo
 
 				if response != "" {
 					al.bus.PublishOutbound(bus.OutboundMessage{
+			Buttons: buttons,
 						Channel: msg.Channel,
 						ChatID:  msg.ChatID,
 						Content: response,
diff --git a/pkg/sentinel/service.go b/pkg/sentinel/service.go
index e438e04..ec342bf 100644
--- a/pkg/sentinel/service.go
+++ b/pkg/sentinel/service.go
@@ -25,7 +25,8 @@ type Service struct {
 	runner     *lifecycle.LoopRunner
 	mu         sync.RWMutex
 	lastAlerts map[string]time.Time
-	mgr        *channels.Manager
+	mgr             *channels.Manager
+	healingChannels map[string]bool
 }
 
 func NewService(cfgPath, workspace string, intervalSec int, autoHeal bool, onAlert AlertFunc) *Service {
@@ -40,6 +41,7 @@ func NewService(cfgPath, workspace string, intervalSec int, autoHeal bool, onAle
 		onAlert:    onAlert,
 		runner:     lifecycle.NewLoopRunner(),
 		lastAlerts: map[string]time.Time{},
+		healingChannels: map[string]bool{},
 	}
 }
 
@@ -108,8 +110,22 @@ func (s *Service) checkChannels() []string {
 			msg := fmt.Sprintf("sentinel: channel %s health check failed: %v", name, err)
 			issues = append(issues, msg)
 			if s.autoHeal {
+				s.mu.Lock()
+				if s.healingChannels[name] {
+					s.mu.Unlock()
+					continue
+				}
+				s.healingChannels[name] = true
+				s.mu.Unlock()
+
 				go func(n string) {
+					defer func() {
+						s.mu.Lock()
+						delete(s.healingChannels, n)
+						s.mu.Unlock()
+					}()
 					logger.InfoCF("sentinel", "Attempting auto-heal for channel", map[string]interface{}{"channel": n})
+					// Use a fresh context for restart to avoid being canceled by sentinel loop
 					if rErr := s.mgr.RestartChannel(context.Background(), n); rErr != nil {
 						logger.ErrorCF("sentinel", "Auto-heal restart failed", map[string]interface{}{"channel": n, "error": rErr.Error()})
 					} else {
diff --git a/pkg/tools/message.go b/pkg/tools/message.go
index e090234..6fdaffd 100644
--- a/pkg/tools/message.go
+++ b/pkg/tools/message.go
@@ -3,9 +3,10 @@ package tools
 import (
 	"context"
 	"fmt"
+	"clawgo/pkg/bus"
 )
 
-type SendCallback func(channel, chatID, content string) error
+type SendCallback func(channel, chatID, content string, buttons [][]bus.Button) error
 
 type MessageTool struct {
 	sendCallback   SendCallback
@@ -41,6 +42,21 @@ func (t *MessageTool) Parameters() map[string]interface{} {
 				"type":        "string",
 				"description": "Optional: target chat/user ID",
 			},
+			"buttons": map[string]interface{}{
+				"type":        "array",
+				"description": "Optional: buttons to include in the message (2D array: rows of buttons)",
+				"items": map[string]interface{}{
+					"type": "array",
+					"items": map[string]interface{}{
+						"type": "object",
+						"properties": map[string]interface{}{
+							"text": map[string]interface{}{"type": "string", "description": "Button text"},
+							"data": map[string]interface{}{"type": "string", "description": "Callback data"},
+						},
+						"required": []string{"text", "data"},
+					},
+				},
+			},
 		},
 		"required": []string{"content"},
 	}
@@ -79,7 +95,28 @@ func (t *MessageTool) Execute(ctx context.Context, args map[string]interface{})
 		return "Error: Message sending not configured", nil
 	}
 
-	if err := t.sendCallback(channel, chatID, content); err != nil {
+	var buttons [][]bus.Button
+	if btns, ok := args["buttons"].([]interface{}); ok {
+		for _, row := range btns {
+			if rowArr, ok := row.([]interface{}); ok {
+				var buttonRow []bus.Button
+				for _, b := range rowArr {
+					if bMap, ok := b.(map[string]interface{}); ok {
+						text, _ := bMap["text"].(string)
+						data, _ := bMap["data"].(string)
+						if text != "" && data != "" {
+							buttonRow = append(buttonRow, bus.Button{Text: text, Data: data})
+						}
+					}
+				}
+				if len(buttonRow) > 0 {
+					buttons = append(buttons, buttonRow)
+				}
+			}
+		}
+	}
+
+	if err := t.sendCallback(channel, chatID, content, buttons); err != nil {
 		return fmt.Sprintf("Error sending message: %v", err), nil
 	}