diff --git a/cmd/gateway.go b/cmd/gateway.go
index dda07bf1..985a179b 100644
--- a/cmd/gateway.go
+++ b/cmd/gateway.go
@@ -677,6 +677,7 @@ func runGateway() {
 					ChatID:   meta.ChatID,
 					AgentID:  meta.LeadAgent,
 					UserID:   meta.UserID,
+					PeerKind: meta.PeerKind,
 					Content:  leaderContent,
 					Metadata: map[string]string{"run_kind": tools.RunKindNotification},
 				})
@@ -825,6 +826,7 @@ func runGateway() {
 				ChatID:    payload.ChatID,
 				UserID:    payload.UserID,
 				LeadAgent: leadAgentKey,
+				PeerKind:  payload.PeerKind,
 			})
 		})
 		slog.Info("team progress notification subscriber registered")
diff --git a/cmd/gateway_consumer_handlers.go b/cmd/gateway_consumer_handlers.go
index 3b28e09d..a0124b94 100644
--- a/cmd/gateway_consumer_handlers.go
+++ b/cmd/gateway_consumer_handlers.go
@@ -309,11 +309,12 @@ func handleTeammateMessage(
 			teamID, _ := uuid.Parse(inMeta[tools.MetaTeamID])
 			if teamTaskID != uuid.Nil {
 				meta := teammateTaskMeta{
-					TaskID:  teamTaskID,
-					TeamID:  teamID,
-					ToAgent: inMeta[tools.MetaToAgent],
-					Channel: inMeta[tools.MetaOriginChannel],
-					ChatID:  inMeta[tools.MetaOriginChatID],
+					TaskID:   teamTaskID,
+					TeamID:   teamID,
+					ToAgent:  inMeta[tools.MetaToAgent],
+					Channel:  inMeta[tools.MetaOriginChannel],
+					ChatID:   inMeta[tools.MetaOriginChatID],
+					PeerKind: inMeta[tools.MetaOriginPeerKind],
 				}
 				cachedTeam = resolveTeamTaskOutcome(ctx, deps, outcome, taskActionFlags, meta)
 			}
diff --git a/cmd/gateway_consumer_post_turn.go b/cmd/gateway_consumer_post_turn.go
index 1ef590f9..8239e9c2 100644
--- a/cmd/gateway_consumer_post_turn.go
+++ b/cmd/gateway_consumer_post_turn.go
@@ -51,6 +51,7 @@ type teammateTaskMeta struct {
 	ToAgent    string
 	Channel    string
 	ChatID     string
+	PeerKind   string // "group" or "direct" — for correct notification routing (#266)
 	Subject    string
 	TaskNumber int
 }
@@ -96,6 +97,7 @@ func resolveTeamTaskOutcome(
 	taskNumber := meta.TaskNumber
 	taskChannel := meta.Channel
 	taskChatID := meta.ChatID
+	taskPeerKind := meta.PeerKind
 
 	// Enrich with live task data if available.
 	if currentTask != nil {
@@ -111,6 +113,11 @@ func resolveTeamTaskOutcome(
 		if currentTask.ChatID != "" {
 			taskChatID = currentTask.ChatID
 		}
+		if taskPeerKind == "" && currentTask.Metadata != nil {
+			if pk, ok := currentTask.Metadata[tools.TaskMetaPeerKind].(string); ok && pk != "" {
+				taskPeerKind = pk
+			}
+		}
 	}
 
 	// Smart post-turn decision based on action flags.
@@ -129,6 +136,7 @@ func resolveTeamTaskOutcome(
 				tools.WithReason(outcome.Err.Error()),
 				tools.WithChannel(taskChannel),
 				tools.WithChatID(taskChatID),
+				tools.WithPeerKind(taskPeerKind),
 				tools.WithTimestamp(now),
 			))
 		}
@@ -162,6 +170,7 @@ func resolveTeamTaskOutcome(
 				tools.WithReason("loop_detector_kill"),
 				tools.WithChannel(taskChannel),
 				tools.WithChatID(taskChatID),
+				tools.WithPeerKind(taskPeerKind),
 				tools.WithTimestamp(now),
 			))
 		}
@@ -195,6 +204,7 @@ func resolveTeamTaskOutcome(
 				tools.WithOwnerAgentKey(toAgent),
 				tools.WithChannel(taskChannel),
 				tools.WithChatID(taskChatID),
+				tools.WithPeerKind(taskPeerKind),
 				tools.WithTimestamp(now),
 			))
 		}
diff --git a/internal/agent/loop_team_reminders.go b/internal/agent/loop_team_reminders.go
index 3138882c..159e5f34 100644
--- a/internal/agent/loop_team_reminders.go
+++ b/internal/agent/loop_team_reminders.go
@@ -64,14 +64,14 @@ func (l *Loop) injectTeamTaskReminders(ctx context.Context, req *RunRequest, mes
 				}
 				if len(parts) > 0 {
 					reminder := "[System] " + strings.Join(parts, "\n\n")
-					// Pop user message, inject reminder, push user message back
+					// Merge reminder into the user message as a prefix tag.
+					// Previous approach injected [user]+[assistant]+[user] which caused
+					// LLMs to treat the assistant ack as "turn complete" → NO_REPLY (#266).
 					userMsg := messages[len(messages)-1]
-					messages = messages[:len(messages)-1]
-					messages = append(messages,
-						providers.Message{Role: "user", Content: reminder},
-						providers.Message{Role: "assistant", Content: "I see the task status. Let me handle accordingly."},
-						userMsg,
-					)
+					messages[len(messages)-1] = providers.Message{
+						Role:    "user",
+						Content: "[Active team tasks]\n" + reminder + "\n[/Active team tasks]\n\n" + userMsg.Content,
+					}
 				}
 			}
 		}
@@ -90,14 +90,12 @@ func (l *Loop) injectTeamTaskReminders(ctx context.Context, req *RunRequest, mes
 						"Stay focused on this task. Your final response becomes the task result — make it clear and complete. "+
 						"For long tasks, report progress: team_tasks(action=\"progress\", percent=50, text=\"status\").",
 					task.TaskNumber, task.Subject)
-				// Pop user message, inject reminder, push user message back
+				// Merge reminder into user message as prefix tag (#266).
 				userMsg := messages[len(messages)-1]
-				messages = messages[:len(messages)-1]
-				messages = append(messages,
-					providers.Message{Role: "user", Content: reminder},
-					providers.Message{Role: "assistant", Content: "Understood. I'll focus on this task and report progress."},
-					userMsg,
-				)
+				messages[len(messages)-1] = providers.Message{
+					Role:    "user",
+					Content: "[Task context]\n" + reminder + "\n[/Task context]\n\n" + userMsg.Content,
+				}
 			}
 		}
 	}
diff --git a/internal/tasks/task_ticker.go b/internal/tasks/task_ticker.go
index 1c086ddb..13ccf9a3 100644
--- a/internal/tasks/task_ticker.go
+++ b/internal/tasks/task_ticker.go
@@ -235,12 +235,21 @@ func (t *TaskTicker) notifyLeaders(ctx context.Context, tasks []store.RecoveredT
 			chatID = scope.TeamID.String()
 		}
 
+		// Resolve PeerKind from first task's metadata for correct session routing (#266).
+		var peerKind string
+		if fullTask, err := t.teams.GetTask(ctx, scopeTasks[0].ID); err == nil && fullTask != nil && fullTask.Metadata != nil {
+			if pk, ok := fullTask.Metadata["peer_kind"].(string); ok {
+				peerKind = pk
+			}
+		}
+
 		if !t.msgBus.TryPublishInbound(bus.InboundMessage{
 			Channel:  channel,
 			SenderID: "ticker:system",
 			ChatID:   chatID,
 			AgentID:  lead.AgentKey,
 			UserID:   team.CreatedBy,
+			PeerKind: peerKind,
 			TenantID: scope.TenantID,
 			Content:  content,
 		}) {
diff --git a/internal/tools/team_event_helpers.go b/internal/tools/team_event_helpers.go
index b277da29..a7a66fae 100644
--- a/internal/tools/team_event_helpers.go
+++ b/internal/tools/team_event_helpers.go
@@ -90,6 +90,11 @@ func WithChatID(id string) TaskEventOption {
 	return func(p *protocol.TeamTaskEventPayload) { p.ChatID = id }
 }
 
+// WithPeerKind sets PeerKind on the payload for correct session routing (#266).
+func WithPeerKind(pk string) TaskEventOption {
+	return func(p *protocol.TeamTaskEventPayload) { p.PeerKind = pk }
+}
+
 // WithCommentText sets CommentText on the payload.
 func WithCommentText(t string) TaskEventOption {
 	return func(p *protocol.TeamTaskEventPayload) { p.CommentText = t }
@@ -103,13 +108,14 @@ func WithProgress(percent int, step string) TaskEventOption {
 	}
 }
 
-// WithContextInfo extracts UserID, Channel, and ChatID from the context
+// WithContextInfo extracts UserID, Channel, ChatID, and PeerKind from the context
 // using standard tool context accessors.
 func WithContextInfo(ctx context.Context) TaskEventOption {
 	return func(p *protocol.TeamTaskEventPayload) {
 		p.UserID = store.UserIDFromContext(ctx)
 		p.Channel = ToolChannelFromCtx(ctx)
 		p.ChatID = ToolChatIDFromCtx(ctx)
+		p.PeerKind = ToolPeerKindFromCtx(ctx)
 	}
 }
 
diff --git a/internal/tools/team_notify_queue.go b/internal/tools/team_notify_queue.go
index 3575bf03..fc720639 100644
--- a/internal/tools/team_notify_queue.go
+++ b/internal/tools/team_notify_queue.go
@@ -13,6 +13,7 @@ type NotifyRoutingMeta struct {
 	ChatID    string
 	UserID    string
 	LeadAgent string // agent key (only used in leader mode)
+	PeerKind  string // "group" or "direct" — routes to correct session (#266)
 }
 
 // TeamNotifyQueue batches team task notifications per chat with debounce,
diff --git a/internal/tools/team_tasks_blocker.go b/internal/tools/team_tasks_blocker.go
index 2b11b2bb..a994fd77 100644
--- a/internal/tools/team_tasks_blocker.go
+++ b/internal/tools/team_tasks_blocker.go
@@ -45,6 +45,10 @@ func (t *TeamTasksTool) handleBlockerComment(
 	// 2. Notify subscriber → "❌ Task failed" → chat channel (direct outbound)
 	// 3. WS broadcast → web UI dashboard real-time update
 	memberKey := t.manager.AgentKeyFromID(ctx, agentID)
+	blockerPeerKind := ""
+	if pk, ok := task.Metadata[TaskMetaPeerKind].(string); ok {
+		blockerPeerKind = pk
+	}
 	t.manager.BroadcastTeamEvent(ctx, protocol.EventTeamTaskFailed, BuildTaskEventPayload(
 		team.ID.String(), taskID.String(),
 		store.TeamTaskStatusFailed,
@@ -55,6 +59,7 @@ func (t *TeamTasksTool) handleBlockerComment(
 		WithUserID(store.UserIDFromContext(ctx)),
 		WithChannel(task.Channel),
 		WithChatID(task.ChatID),
+		WithPeerKind(blockerPeerKind),
 	))
 
 	// Escalate to leader if enabled in team settings.
@@ -74,6 +79,7 @@ func (t *TeamTasksTool) handleBlockerComment(
 				ChatID:   task.ChatID,
 				Content:  escalationMsg,
 				UserID:   store.UserIDFromContext(ctx),
+				PeerKind: blockerPeerKind,
 				TenantID: store.TenantIDFromContext(ctx),
 				AgentID:  leadAg.AgentKey,
 			}) {
diff --git a/internal/tools/team_tasks_create.go b/internal/tools/team_tasks_create.go
index 00b8bbe3..405c7b6c 100644
--- a/internal/tools/team_tasks_create.go
+++ b/internal/tools/team_tasks_create.go
@@ -290,6 +290,7 @@ func (t *TeamTasksTool) executeCreate(ctx context.Context, args map[string]any)
 					WithOwnerAgentKey(t.manager.AgentKeyFromID(ctx, assigneeID)),
 					WithChannel(task.Channel),
 					WithChatID(task.ChatID),
+					WithPeerKind(ToolPeerKindFromCtx(ctx)),
 				))
 				t.manager.DispatchTaskToAgent(ctx, task, team, assigneeID)
 			}
diff --git a/internal/tools/team_tool_dispatch.go b/internal/tools/team_tool_dispatch.go
index 894ca50c..51e6f0be 100644
--- a/internal/tools/team_tool_dispatch.go
+++ b/internal/tools/team_tool_dispatch.go
@@ -359,6 +359,10 @@ func (m *TeamToolManager) DispatchUnblockedTasks(ctx context.Context, teamID uui
 			continue
 		}
 		dispatched[ownerID] = true
+		taskPeerKind := ""
+		if pk, ok := task.Metadata[TaskMetaPeerKind].(string); ok {
+			taskPeerKind = pk
+		}
 		m.broadcastTeamEvent(ctx, protocol.EventTeamTaskDispatched, BuildTaskEventPayload(
 			teamID.String(), task.ID.String(),
 			store.TeamTaskStatusInProgress,
@@ -367,6 +371,7 @@ func (m *TeamToolManager) DispatchUnblockedTasks(ctx context.Context, teamID uui
 			WithOwnerAgentKey(m.agentKeyFromID(ctx, ownerID)),
 			WithChannel(task.Channel),
 			WithChatID(task.ChatID),
+			WithPeerKind(taskPeerKind),
 		))
 
 		// Append completed blocker results so the member agent has context.
diff --git a/internal/tools/team_tool_validation.go b/internal/tools/team_tool_validation.go
index f0c459bc..81f0dc57 100644
--- a/internal/tools/team_tool_validation.go
+++ b/internal/tools/team_tool_validation.go
@@ -98,6 +98,10 @@ func (m *TeamToolManager) ProcessPendingTasks(ctx context.Context, teamID uuid.U
 			slog.Warn("post_turn: assign failed", "task_id", task.ID, "error", err)
 			continue
 		}
+		taskPeerKind := ""
+		if pk, ok := task.Metadata[TaskMetaPeerKind].(string); ok {
+			taskPeerKind = pk
+		}
 		m.broadcastTeamEvent(ctx, protocol.EventTeamTaskDispatched, BuildTaskEventPayload(
 			teamID.String(), task.ID.String(),
 			store.TeamTaskStatusInProgress,
@@ -106,6 +110,7 @@ func (m *TeamToolManager) ProcessPendingTasks(ctx context.Context, teamID uuid.U
 			WithOwnerAgentKey(m.agentKeyFromID(ctx, *task.OwnerAgentID)),
 			WithChannel(task.Channel),
 			WithChatID(task.ChatID),
+			WithPeerKind(taskPeerKind),
 		))
 		// Restore leader's trace context from task metadata (ctx here is the
 		// consumer goroutine context which has no trace after the turn ends).
@@ -177,6 +182,7 @@ func (m *TeamToolManager) notifyLeaderCycleError(ctx context.Context, teamID uui
 		ChatID:   chatID,
 		AgentID:  leadAgent.AgentKey,
 		UserID:   team.CreatedBy,
+		PeerKind: ToolPeerKindFromCtx(ctx),
 		TenantID: store.TenantIDFromContext(ctx),
 		Content:  content,
 	})
diff --git a/pkg/protocol/team_events.go b/pkg/protocol/team_events.go
index 1a359388..5af4fcf0 100644
--- a/pkg/protocol/team_events.go
+++ b/pkg/protocol/team_events.go
@@ -100,6 +100,7 @@ type TeamTaskEventPayload struct {
 	UserID           string `json:"user_id"`
 	Channel          string `json:"channel"`
 	ChatID           string `json:"chat_id"`
+	PeerKind         string `json:"peer_kind,omitempty"` // "group" or "direct" — for correct session routing (#266)
 	Timestamp        string `json:"timestamp"`
 
 	// Comment text preview (for team.task.commented events, truncated).