diff --git a/pkg/agent/loop_test.go b/pkg/agent/loop_test.go
index a2d4ea7aa..62ad381f6 100644
--- a/pkg/agent/loop_test.go
+++ b/pkg/agent/loop_test.go
@@ -1183,6 +1183,72 @@ func TestRunAgentLoop_ResponseHandledToolPublishesForUserWhenSendResponseDisable
 	}
 }
 
+func TestRunAgentLoop_ErrorToolPublishesForUserWhenSendResponseDisabled(t *testing.T) {
+	tmpDir := t.TempDir()
+	cfg := config.DefaultConfig()
+	cfg.Agents.Defaults.Workspace = tmpDir
+	cfg.Agents.Defaults.ModelName = "test-model"
+	cfg.Agents.Defaults.MaxTokens = 4096
+	cfg.Agents.Defaults.MaxToolIterations = 10
+
+	msgBus := bus.NewMessageBus()
+	provider := &errorToolProvider{}
+	al := NewAgentLoop(cfg, msgBus, provider)
+
+	store := media.NewFileMediaStore()
+	al.SetMediaStore(store)
+	telegramChannel := &fakeMediaChannel{fakeChannel: fakeChannel{id: "rid-telegram"}}
+	al.SetChannelManager(newStartedTestChannelManager(t, msgBus, store, "telegram", telegramChannel))
+	al.RegisterTool(&errorTool{})
+
+	defaultAgent := al.registry.GetDefaultAgent()
+	if defaultAgent == nil {
+		t.Fatal("expected default agent")
+	}
+
+	response, err := al.runAgentLoop(context.Background(), defaultAgent, processOptions{
+		Dispatch: DispatchRequest{
+			SessionKey:  "session-error-tool",
+			UserMessage: "please run failing tool",
+			SessionScope: &session.SessionScope{
+				Version:    session.ScopeVersionV1,
+				AgentID:    defaultAgent.ID,
+				Channel:    "telegram",
+				Dimensions: []string{"chat"},
+				Values: map[string]string{
+					"chat": "direct:chat1",
+				},
+			},
+			InboundContext: &bus.InboundContext{
+				Channel:  "telegram",
+				ChatID:   "chat1",
+				ChatType: "direct",
+				SenderID: "user1",
+			},
+		},
+		DefaultResponse: defaultResponse,
+		EnableSummary:   false,
+		SendResponse:    false,
+	})
+	if err != nil {
+		t.Fatalf("runAgentLoop() error = %v", err)
+	}
+	if response != defaultResponse {
+		t.Fatalf("expected default final response, got %q", response)
+	}
+
+	deadline := time.Now().Add(2 * time.Second)
+	for len(telegramChannel.sentMessages) == 0 && time.Now().Before(deadline) {
+		time.Sleep(10 * time.Millisecond)
+	}
+	if len(telegramChannel.sentMessages) != 1 {
+		t.Fatalf("expected exactly 1 sent text message, got %d", len(telegramChannel.sentMessages))
+	}
+	if telegramChannel.sentMessages[0].Content != "simulated tool failure" {
+		t.Fatalf("unexpected sent text message: %+v", telegramChannel.sentMessages[0])
+	}
+}
+
 func TestAppendEventContextFields_IncludesInboundRouteAndScope(t *testing.T) {
 	fields := map[string]any{}
 
@@ -1609,6 +1675,10 @@ type handledUserProvider struct {
 	calls int
 }
 
+type errorToolProvider struct {
+	calls int
+}
+
 func (m *handledUserProvider) Chat(
 	ctx context.Context,
 	messages []providers.Message,
@@ -1635,6 +1705,32 @@ func (m *handledUserProvider) GetDefaultModel() string {
 	return "handled-user-model"
 }
 
+func (m *errorToolProvider) Chat(
+	ctx context.Context,
+	messages []providers.Message,
+	tools []providers.ToolDefinition,
+	model string,
+	opts map[string]any,
+) (*providers.LLMResponse, error) {
+	m.calls++
+	if m.calls == 1 {
+		return &providers.LLMResponse{
+			Content: "Running the requested tool.",
+			ToolCalls: []providers.ToolCall{{
+				ID:        "call_error_tool",
+				Type:      "function",
+				Name:      "error_tool",
+				Arguments: map[string]any{},
+			}},
+		}, nil
+	}
+	return &providers.LLMResponse{}, nil
+}
+
+func (m *errorToolProvider) GetDefaultModel() string {
+	return "error-tool-model"
+}
+
 type messageToolProvider struct {
 	calls int
 }
@@ -2021,6 +2117,8 @@ func (m *handledMediaTool) Execute(ctx context.Context, args map[string]any) *to
 
 type handledUserTool struct{}
 
+type errorTool struct{}
+
 func (m *handledUserTool) Name() string { return "handled_user_tool" }
 func (m *handledUserTool) Description() string {
 	return "Returns a user-visible result and marks delivery as handled"
@@ -2037,6 +2135,22 @@ func (m *handledUserTool) Execute(ctx context.Context, args map[string]any) *too
 	return tools.UserResult("Handled user output from tool.").WithResponseHandled()
 }
 
+func (m *errorTool) Name() string { return "error_tool" }
+func (m *errorTool) Description() string {
+	return "Returns a tool error for testing delivery behavior"
+}
+
+func (m *errorTool) Parameters() map[string]any {
+	return map[string]any{
+		"type":       "object",
+		"properties": map[string]any{},
+	}
+}
+
+func (m *errorTool) Execute(ctx context.Context, args map[string]any) *tools.ToolResult {
+	return tools.ErrorResult("simulated tool failure")
+}
+
 type handledMediaWithSteeringProvider struct {
 	calls int
 }
diff --git a/pkg/agent/loop_turn.go b/pkg/agent/loop_turn.go
index 406120e46..bdf6119aa 100644
--- a/pkg/agent/loop_turn.go
+++ b/pkg/agent/loop_turn.go
@@ -1263,15 +1263,20 @@ turnLoop:
 				allResponsesHandled = false
 			}
 
+			forUserContent := toolResult.ForUser
+			if toolResult.IsError && forUserContent == "" {
+				forUserContent = toolResult.ContentForLLM()
+			}
+
 			shouldSendForUser := !toolResult.Silent &&
-				toolResult.ForUser != "" &&
-				(ts.opts.SendResponse || toolResult.ResponseHandled)
+				forUserContent != "" &&
+				(ts.opts.SendResponse || toolResult.ResponseHandled || toolResult.IsError)
 			if shouldSendForUser {
-				al.bus.PublishOutbound(ctx, outboundMessageForTurn(ts, toolResult.ForUser))
+				al.bus.PublishOutbound(ctx, outboundMessageForTurn(ts, forUserContent))
 				logger.DebugCF("agent", "Sent tool result to user",
 					map[string]any{
 						"tool":        toolName,
-						"content_len": len(toolResult.ForUser),
+						"content_len": len(forUserContent),
 					})
 			}
 			contentForLLM := toolResult.ContentForLLM()