diff --git a/pkg/agent/loop.go b/pkg/agent/loop.go
index eeb1c48fd..080012ee3 100644
--- a/pkg/agent/loop.go
+++ b/pkg/agent/loop.go
@@ -410,16 +410,16 @@ func (al *AgentLoop) bindAdvancedMessageManagers(cm *channels.Manager) {
 		if advancedManager, ok := t.(tools.AdvancedMessageManager); ok {
 			advancedManager.SetCallbacks(
 				// sendPlaceholder
-				func(channelName, chatID, content string) (string, error) {
-					return cm.SendMessageWithID(context.Background(), bus.OutboundMessage{
+				func(ctx context.Context, channelName, chatID, content string) (string, error) {
+					return cm.SendMessageWithID(ctx, bus.OutboundMessage{
 						Channel: channelName,
 						ChatID:  chatID,
 						Content: content,
 					})
 				},
 				// editMessage
-				func(channelName, chatID, messageID, content string) error {
-					return cm.EditMessage(context.Background(), channelName, chatID, messageID, content)
+				func(ctx context.Context, channelName, chatID, messageID, content string) error {
+					return cm.EditMessage(ctx, channelName, chatID, messageID, content)
 				},
 			)
 		}
diff --git a/pkg/channels/feishu/feishu_64.go b/pkg/channels/feishu/feishu_64.go
index 00f73064d..620322cb4 100644
--- a/pkg/channels/feishu/feishu_64.go
+++ b/pkg/channels/feishu/feishu_64.go
@@ -22,6 +22,7 @@ import (
 	"github.com/sipeed/picoclaw/pkg/bus"
 	"github.com/sipeed/picoclaw/pkg/channels"
 	"github.com/sipeed/picoclaw/pkg/config"
+	"github.com/sipeed/picoclaw/pkg/fileutil"
 	"github.com/sipeed/picoclaw/pkg/identity"
 	"github.com/sipeed/picoclaw/pkg/logger"
 	"github.com/sipeed/picoclaw/pkg/media"
@@ -612,7 +613,7 @@ func (c *FeishuChannel) downloadResource(
 		return ""
 	}
 	ext := filepath.Ext(filename)
-	localPath := filepath.Join(mediaDir, utils.SanitizeFilename(messageID+"-"+fileKey+ext))
+	localPath := filepath.Join(mediaDir, fileutil.SanitizeFilename(messageID+"-"+fileKey+ext))
 
 	out, err := os.Create(localPath)
 	if err != nil {
diff --git a/pkg/channels/manager.go b/pkg/channels/manager.go
index 655ff49fa..65c05b46f 100644
--- a/pkg/channels/manager.go
+++ b/pkg/channels/manager.go
@@ -849,9 +849,13 @@ func (m *Manager) SendMessageWithID(ctx context.Context, msg bus.OutboundMessage
 			return msgID, nil
 		}
 		logger.ErrorCF("manager", "SendMessageWithID failed", map[string]any{"error": err, "msgID": msgID})
-		logger.WarnCF("manager", "channel does not implement SyncSender", map[string]any{"channel": msg.Channel})
+		if err == nil {
+			err = fmt.Errorf("sync sender returned empty message ID")
+		}
+		return "", err
 	}
 
+	logger.WarnCF("manager", "channel does not implement SyncSender", map[string]any{"channel": msg.Channel})
 	logger.WarnCF("manager", "falling back to bus publish", nil)
 	m.bus.PublishOutbound(ctx, msg)
 
diff --git a/pkg/config/config.go b/pkg/config/config.go
index 134673754..e8bb60274 100644
--- a/pkg/config/config.go
+++ b/pkg/config/config.go
@@ -675,7 +675,7 @@ type TaskToolConfig struct {
 }
 
 type TaskToolIconsConfig struct {
-	Pending    string `json:"pending"     env:"PICOCLAW_TOOLS_TASK_TOOL_ICONS_PENDING"    default:"⚪"`
+	Pending    string `json:"pending"     env:"PICOCLAW_TOOLS_TASK_TOOL_ICONS_PENDING"    default:"🔘"`
 	InProgress string `json:"in_progress" env:"PICOCLAW_TOOLS_TASK_TOOL_ICONS_IN_PROGRESS" default:"🟡"`
 	Completed  string `json:"completed"   env:"PICOCLAW_TOOLS_TASK_TOOL_ICONS_COMPLETED"  default:"🟢"`
 	Failed     string `json:"failed"      env:"PICOCLAW_TOOLS_TASK_TOOL_ICONS_FAILED"     default:"🔴"`
diff --git a/pkg/fileutil/file.go b/pkg/fileutil/file.go
index 7ca872374..13d37068f 100644
--- a/pkg/fileutil/file.go
+++ b/pkg/fileutil/file.go
@@ -11,9 +11,27 @@ import (
 	"fmt"
 	"os"
 	"path/filepath"
+	"strings"
 	"time"
 )
 
+// SanitizeFilename removes potentially dangerous characters from a filename
+// and returns a safe version for local filesystem storage.
+func SanitizeFilename(filename string) string {
+	// First, replace common directory separators and colons with underscores
+	safe := strings.ReplaceAll(filename, "/", "_")
+	safe = strings.ReplaceAll(safe, "\\", "_")
+	safe = strings.ReplaceAll(safe, ":", "_")
+
+	// Then get the base filename to ensure no path components remain
+	base := filepath.Base(safe)
+
+	// Finally, remove any exact ".." sequences that might have slipped through
+	base = strings.ReplaceAll(base, "..", "")
+
+	return base
+}
+
 // WriteFileAtomic atomically writes data to a file using a temp file + rename pattern.
 //
 // This guarantees that the target file is either:
diff --git a/pkg/session/manager.go b/pkg/session/manager.go
index 08f0b0ad2..f39a92d1e 100644
--- a/pkg/session/manager.go
+++ b/pkg/session/manager.go
@@ -8,6 +8,7 @@ import (
 	"sync"
 	"time"
 
+	"github.com/sipeed/picoclaw/pkg/fileutil"
 	"github.com/sipeed/picoclaw/pkg/providers"
 )
 
@@ -145,21 +146,12 @@ func (sm *SessionManager) TruncateHistory(key string, keepLast int) {
 	session.Updated = time.Now()
 }
 
-// sanitizeFilename converts a session key into a cross-platform safe filename.
-// Session keys use "channel:chatID" (e.g. "telegram:123456") but ':' is the
-// volume separator on Windows, so filepath.Base would misinterpret the key.
-// We replace it with '_'. The original key is preserved inside the JSON file,
-// so loadSessions still maps back to the right in-memory key.
-func sanitizeFilename(key string) string {
-	return strings.ReplaceAll(key, ":", "_")
-}
-
 func (sm *SessionManager) Save(key string) error {
 	if sm.storage == "" {
 		return nil
 	}
 
-	filename := sanitizeFilename(key)
+	filename := fileutil.SanitizeFilename(key)
 
 	// filepath.IsLocal rejects empty names, "..", absolute paths, and
 	// OS-reserved device names (NUL, COM1 … on Windows).
diff --git a/pkg/session/manager_test.go b/pkg/session/manager_test.go
index 5ef5f4349..a1a427485 100644
--- a/pkg/session/manager_test.go
+++ b/pkg/session/manager_test.go
@@ -4,6 +4,8 @@ import (
 	"os"
 	"path/filepath"
 	"testing"
+
+	"github.com/sipeed/picoclaw/pkg/fileutil"
 )
 
 func TestSanitizeFilename(t *testing.T) {
@@ -21,9 +23,9 @@ func TestSanitizeFilename(t *testing.T) {
 
 	for _, tt := range tests {
 		t.Run(tt.input, func(t *testing.T) {
-			got := sanitizeFilename(tt.input)
+			got := fileutil.SanitizeFilename(tt.input)
 			if got != tt.expected {
-				t.Errorf("sanitizeFilename(%q) = %q, want %q", tt.input, got, tt.expected)
+				t.Errorf("SanitizeFilename(%q) = %q, want %q", tt.input, got, tt.expected)
 			}
 		})
 	}
diff --git a/pkg/session/tasks.go b/pkg/session/tasks.go
index 7402dd3f2..48f0c2aeb 100644
--- a/pkg/session/tasks.go
+++ b/pkg/session/tasks.go
@@ -10,6 +10,7 @@ import (
 	"time"
 
 	"github.com/sipeed/picoclaw/pkg/fileutil"
+	"github.com/sipeed/picoclaw/pkg/logger"
 )
 
 type TaskStatus string
@@ -48,12 +49,25 @@ func NewTaskManager(storage string) *TaskManager {
 	}
 	if storage != "" {
 		if err := tm.loadAll(); err != nil {
-			// just log
+			logger.ErrorCF("tasks", "Failed to load session tasks on startup", map[string]any{
+				"error": err.Error(),
+			})
 		}
 	}
 	return tm
 }
 
+func (tm *TaskManager) Get(sessionKey string) *SessionTasks {
+	tm.mu.RLock()
+	defer tm.mu.RUnlock()
+
+	tasks, ok := tm.tasks[sessionKey]
+	if ok {
+		return tasks
+	}
+	return nil
+}
+
 func (tm *TaskManager) GetOrCreate(sessionKey string) *SessionTasks {
 	tm.mu.Lock()
 	defer tm.mu.Unlock()
@@ -137,7 +151,10 @@ func (tm *TaskManager) Save(key string) error {
 		return nil
 	}
 
-	filename := sanitizeFilenameTasks(key) + "_tasks.json"
+	if err := os.MkdirAll(tm.storage, 0o755); err != nil {
+		return err
+	}
+	filename := fileutil.SanitizeFilename(key) + "_tasks.json"
 
 	if filename == "." || !filepath.IsLocal(filename) || strings.ContainsAny(filename, "/\\") {
 		return os.ErrInvalid
@@ -198,9 +215,3 @@ func (tm *TaskManager) loadAll() error {
 	}
 	return nil
 }
-
-// Ensure sanitizeFilename is accessible by importing from another file or duplicating.
-// For now, copying it since it's an unexported utility in manager.go.
-func sanitizeFilenameTasks(key string) string {
-	return strings.ReplaceAll(key, ":", "_")
-}
diff --git a/pkg/tools/base.go b/pkg/tools/base.go
index 426536b0b..ea0fb792a 100644
--- a/pkg/tools/base.go
+++ b/pkg/tools/base.go
@@ -97,7 +97,7 @@ func ToolToSchema(tool Tool) map[string]any {
 type AdvancedMessageManager interface {
 	Tool
 	SetCallbacks(
-		sendPlaceholder func(channel, chatID, content string) (string, error),
-		editMessage func(channel, chatID, messageID, content string) error,
+		sendPlaceholder func(ctx context.Context, channel, chatID, content string) (string, error),
+		editMessage func(ctx context.Context, channel, chatID, messageID, content string) error,
 	)
 }
diff --git a/pkg/tools/tasktool.go b/pkg/tools/tasktool.go
index 734e408cc..ece838073 100644
--- a/pkg/tools/tasktool.go
+++ b/pkg/tools/tasktool.go
@@ -7,29 +7,18 @@ import (
 	"strings"
 
 	"github.com/sipeed/picoclaw/pkg/config"
+	"github.com/sipeed/picoclaw/pkg/logger"
 	"github.com/sipeed/picoclaw/pkg/session"
 )
 
 type TaskTool struct {
 	taskManager     *session.TaskManager
-	sendPlaceholder func(channel, chatID, content string) (string, error)
-	editMessage     func(channel, chatID, messageID, content string) error
+	sendPlaceholder func(ctx context.Context, channel, chatID, content string) (string, error)
+	editMessage     func(ctx context.Context, channel, chatID, messageID, content string) error
 	icons           config.TaskToolIconsConfig
 }
 
 func NewTaskTool(taskManager *session.TaskManager, icons config.TaskToolIconsConfig) *TaskTool {
-	if icons.Pending == "" {
-		icons.Pending = "🔘"
-	}
-	if icons.InProgress == "" {
-		icons.InProgress = "🟡"
-	}
-	if icons.Completed == "" {
-		icons.Completed = "🟢"
-	}
-	if icons.Failed == "" {
-		icons.Failed = "🔴"
-	}
 
 	return &TaskTool{
 		taskManager: taskManager,
@@ -95,8 +84,8 @@ func (t *TaskTool) Parameters() map[string]any {
 }
 
 func (t *TaskTool) SetCallbacks(
-	sendPlaceholder func(channel, chatID, content string) (string, error),
-	editMessage func(channel, chatID, messageID, content string) error,
+	sendPlaceholder func(ctx context.Context, channel, chatID, content string) (string, error),
+	editMessage func(ctx context.Context, channel, chatID, messageID, content string) error,
 ) {
 	t.sendPlaceholder = sendPlaceholder
 	t.editMessage = editMessage
@@ -122,19 +111,19 @@ func (t *TaskTool) Execute(ctx context.Context, args map[string]any) *ToolResult
 
 	switch action {
 	case "create_plan":
-		return t.handleCreatePlan(sessionKey, channel, chatID, args)
+		return t.handleCreatePlan(ctx, sessionKey, channel, chatID, args)
 	case "update_task":
-		return t.handleUpdateTask(sessionKey, channel, chatID, args)
+		return t.handleUpdateTask(ctx, sessionKey, channel, chatID, args)
 	case "list_plan":
 		return t.handleListPlan(sessionKey)
 	case "resend_plan":
-		return t.handleResendPlan(sessionKey, channel, chatID)
+		return t.handleResendPlan(ctx, sessionKey, channel, chatID)
 	default:
 		return &ToolResult{ForLLM: fmt.Sprintf("tasktool: unknown action '%s'", action), IsError: true}
 	}
 }
 
-func (t *TaskTool) handleCreatePlan(sessionKey, channel, chatID string, args map[string]any) *ToolResult {
+func (t *TaskTool) handleCreatePlan(ctx context.Context, sessionKey, channel, chatID string, args map[string]any) *ToolResult {
 	tasksRaw, ok := args["tasks"].([]interface{})
 	if !ok || len(tasksRaw) == 0 {
 		return &ToolResult{ForLLM: "tasktool: tasks array is required and cannot be empty for 'create_plan'", IsError: true}
@@ -170,7 +159,7 @@ func (t *TaskTool) handleCreatePlan(sessionKey, channel, chatID string, args map
 
 	// Send message through callback if available
 	if t.sendPlaceholder != nil {
-		msgID, err := t.sendPlaceholder(channel, chatID, content)
+		msgID, err := t.sendPlaceholder(ctx, channel, chatID, content)
 		if err == nil && msgID != "" {
 			t.taskManager.SetMessageID(sessionKey, msgID)
 		}
@@ -184,8 +173,8 @@ func (t *TaskTool) handleCreatePlan(sessionKey, channel, chatID string, args map
 }
 
 func (t *TaskTool) handleListPlan(sessionKey string) *ToolResult {
-	st := t.taskManager.GetOrCreate(sessionKey)
-	if len(st.Tasks) == 0 {
+	st := t.taskManager.Get(sessionKey)
+	if st == nil || len(st.Tasks) == 0 {
 		return &ToolResult{
 			ForLLM: "No active plan found for this session.",
 			Silent: true,
@@ -201,7 +190,7 @@ func (t *TaskTool) handleListPlan(sessionKey string) *ToolResult {
 	}
 }
 
-func (t *TaskTool) handleResendPlan(sessionKey, channel, chatID string) *ToolResult {
+func (t *TaskTool) handleResendPlan(ctx context.Context, sessionKey, channel, chatID string) *ToolResult {
 	st := t.taskManager.GetOrCreate(sessionKey)
 	if len(st.Tasks) == 0 {
 		return &ToolResult{
@@ -213,9 +202,13 @@ func (t *TaskTool) handleResendPlan(sessionKey, channel, chatID string) *ToolRes
 	content := t.formatPlanMessage(st.Tasks)
 
 	if t.sendPlaceholder != nil {
-		msgID, err := t.sendPlaceholder(channel, chatID, content)
-		if err == nil && msgID != "" {
-			t.taskManager.SetMessageID(sessionKey, msgID)
+		msgID, err := t.sendPlaceholder(ctx, channel, chatID, content)
+		if err == nil {
+			if msgID != "" {
+				t.taskManager.SetMessageID(sessionKey, msgID)
+			}
+			// If err == nil but msgID == "", the channel delivered the message
+			// (or is async) but doesn't support returning IDs. We consider this a success.
 		} else {
 			return &ToolResult{ForLLM: fmt.Sprintf("Failed to resend message: %v", err), IsError: true}
 		}
@@ -230,7 +223,7 @@ func (t *TaskTool) handleResendPlan(sessionKey, channel, chatID string) *ToolRes
 	}
 }
 
-func (t *TaskTool) handleUpdateTask(sessionKey, channel, chatID string, args map[string]any) *ToolResult {
+func (t *TaskTool) handleUpdateTask(ctx context.Context, sessionKey, channel, chatID string, args map[string]any) *ToolResult {
 	taskID, _ := args["task_id"].(string)
 	if taskID == "" {
 		return &ToolResult{ForLLM: "tasktool: task_id is required for 'update_task'", IsError: true}
@@ -252,10 +245,17 @@ func (t *TaskTool) handleUpdateTask(sessionKey, channel, chatID string, args map
 
 	// Edit message through callback if available
 	if t.editMessage != nil && st.MessageID != "" {
-		_ = t.editMessage(channel, chatID, st.MessageID, content)
+		if err := t.editMessage(ctx, channel, chatID, st.MessageID, content); err != nil {
+			logger.WarnCF("tasktool", "Failed to edit task message", map[string]any{
+				"channel":    channel,
+				"chat_id":    chatID,
+				"message_id": st.MessageID,
+				"error":      err.Error(),
+			})
+		}
 	} else if t.sendPlaceholder != nil && st.MessageID == "" {
 		// Fallback: send new progress message if we didn't have one
-		msgID, err := t.sendPlaceholder(channel, chatID, content)
+		msgID, err := t.sendPlaceholder(ctx, channel, chatID, content)
 		if err == nil && msgID != "" {
 			t.taskManager.SetMessageID(sessionKey, msgID)
 		}
@@ -289,11 +289,11 @@ func (t *TaskTool) formatPlanMessage(tasks []session.Task) string {
 
 		// Primitive markdown-to-html regex parser across multiple lines.
 		// For the description and result, we replace lone underscores to prevent similar italic bugs.
-		safeDesc := strings.ReplaceAll(task.Description, "_", " ")
+		safeDesc := strings.ReplaceAll(task.Description, "_", "\\_")
 
 		sb.WriteString(fmt.Sprintf("%s %s\n", icon, safeDesc))
 		if task.Result != "" {
-			safeResult := strings.ReplaceAll(task.Result, "_", " ")
+			safeResult := strings.ReplaceAll(task.Result, "_", "\\_")
 			sb.WriteString(fmt.Sprintf("    **Result**: %s\n", safeResult))
 		}
 	}
diff --git a/pkg/utils/media.go b/pkg/utils/media.go
index 3e1c5d88e..e6dbb5154 100644
--- a/pkg/utils/media.go
+++ b/pkg/utils/media.go
@@ -11,6 +11,7 @@ import (
 
 	"github.com/google/uuid"
 
+	"github.com/sipeed/picoclaw/pkg/fileutil"
 	"github.com/sipeed/picoclaw/pkg/logger"
 )
 
@@ -34,20 +35,6 @@ func IsAudioFile(filename, contentType string) bool {
 	return false
 }
 
-// SanitizeFilename removes potentially dangerous characters from a filename
-// and returns a safe version for local filesystem storage.
-func SanitizeFilename(filename string) string {
-	// Get the base filename without path
-	base := filepath.Base(filename)
-
-	// Remove any directory traversal attempts
-	base = strings.ReplaceAll(base, "..", "")
-	base = strings.ReplaceAll(base, "/", "_")
-	base = strings.ReplaceAll(base, "\\", "_")
-
-	return base
-}
-
 // DownloadOptions holds optional parameters for downloading files
 type DownloadOptions struct {
 	Timeout      time.Duration
@@ -76,7 +63,7 @@ func DownloadFile(urlStr, filename string, opts DownloadOptions) string {
 	}
 
 	// Generate unique filename with UUID prefix to prevent conflicts
-	safeName := SanitizeFilename(filename)
+	safeName := fileutil.SanitizeFilename(filename)
 	localPath := filepath.Join(mediaDir, uuid.New().String()[:8]+"_"+safeName)
 
 	// Create HTTP request