diff --git a/pkg/agent/agent_tool_test.go b/pkg/agent/agent_tool_test.go
index 2164ec5fd..a95447b21 100644
--- a/pkg/agent/agent_tool_test.go
+++ b/pkg/agent/agent_tool_test.go
@@ -375,6 +375,420 @@ func TestAgentTool_Execute(t *testing.T) {
 	)
 }
 
+func TestAgentTool_Execute_NestedApproval(t *testing.T) {
+	t.Parallel()
+
+	t.Run(
+		"nested agent approval surfaces as InterruptedError",
+		func(t *testing.T) {
+			t.Parallel()
+
+			deleteTool := agent.FunctionTool[struct{}](
+				"delete_file",
+				"Delete a file",
+				func(_ context.Context, _ struct{}) (agent.ToolResult, error) {
+					return agent.ToolResult{Content: "file deleted"}, nil
+				},
+			)
+
+			innerProvider := &mockProvider{
+				responses: []*llm.ChatCompletionResponse{
+					toolCallResponse(llm.ToolCall{
+						ID:       "inner_tc1",
+						Function: llm.FunctionCall{Name: "delete_file", Arguments: `{}`},
+					}),
+				},
+			}
+
+			innerAgent := agent.New(
+				"file_manager",
+				newTestClient(innerProvider),
+				agent.WithModel("test-model"),
+				agent.WithTools(deleteTool),
+				agent.WithApproval(agent.ApprovalConfig{
+					ToolNames: []string{"delete_file"},
+				}),
+			)
+
+			outerProvider := &mockProvider{
+				responses: []*llm.ChatCompletionResponse{
+					toolCallResponse(llm.ToolCall{
+						ID:       "outer_tc1",
+						Function: llm.FunctionCall{Name: "file_expert", Arguments: `{"input":"delete the file"}`},
+					}),
+				},
+			}
+
+			outerAgent := agent.New(
+				"assistant",
+				newTestClient(outerProvider),
+				agent.WithModel("test-model"),
+				agent.WithTools(innerAgent.AsTool("file_expert", "Manage files")),
+			)
+
+			_, err := outerAgent.Run(
+				context.Background(),
+				[]llm.Message{userMessage("Delete the file")},
+			)
+
+			require.Error(t, err)
+			var interrupted *agent.InterruptedError
+			require.ErrorAs(t, err, &interrupted)
+			assert.Len(t, interrupted.PendingApprovals, 1)
+			assert.Equal(t, "delete_file", interrupted.PendingApprovals[0].Function.Name)
+			assert.Equal(t, "file_manager", interrupted.Agent.Name())
+		},
+	)
+
+	t.Run(
+		"nested agent approval can be resumed with approve",
+		func(t *testing.T) {
+			t.Parallel()
+
+			var toolExecuted bool
+
+			deleteTool := agent.FunctionTool[struct{}](
+				"delete_file",
+				"Delete a file",
+				func(_ context.Context, _ struct{}) (agent.ToolResult, error) {
+					toolExecuted = true
+					return agent.ToolResult{Content: "file deleted"}, nil
+				},
+			)
+
+			innerProvider := &mockProvider{
+				responses: []*llm.ChatCompletionResponse{
+					toolCallResponse(llm.ToolCall{
+						ID:       "inner_tc1",
+						Function: llm.FunctionCall{Name: "delete_file", Arguments: `{}`},
+					}),
+					stopResponse("File has been deleted."),
+				},
+			}
+
+			innerAgent := agent.New(
+				"file_manager",
+				newTestClient(innerProvider),
+				agent.WithModel("test-model"),
+				agent.WithTools(deleteTool),
+				agent.WithApproval(agent.ApprovalConfig{
+					ToolNames: []string{"delete_file"},
+				}),
+			)
+
+			outerProvider := &mockProvider{
+				responses: []*llm.ChatCompletionResponse{
+					toolCallResponse(llm.ToolCall{
+						ID:       "outer_tc1",
+						Function: llm.FunctionCall{Name: "file_expert", Arguments: `{"input":"delete the file"}`},
+					}),
+					stopResponse("Done, the file has been deleted."),
+				},
+			}
+
+			outerAgent := agent.New(
+				"assistant",
+				newTestClient(outerProvider),
+				agent.WithModel("test-model"),
+				agent.WithTools(innerAgent.AsTool("file_expert", "Manage files")),
+			)
+
+			_, err := outerAgent.Run(
+				context.Background(),
+				[]llm.Message{userMessage("Delete the file")},
+			)
+
+			var interrupted *agent.InterruptedError
+			require.ErrorAs(t, err, &interrupted)
+			assert.False(t, toolExecuted)
+
+			result, err := agent.Resume(
+				context.Background(),
+				interrupted,
+				agent.ResumeInput{
+					Approvals: map[string]agent.ApprovalResult{
+						"inner_tc1": {Approved: true},
+					},
+				},
+			)
+
+			require.NoError(t, err)
+			assert.True(t, toolExecuted)
+			assert.Equal(t, "Done, the file has been deleted.", result.FinalMessage().Text())
+			assert.Equal(t, "assistant", result.LastAgent.Name())
+		},
+	)
+
+	t.Run(
+		"nested agent rejection resumes outer agent",
+		func(t *testing.T) {
+			t.Parallel()
+
+			deleteTool := agent.FunctionTool[struct{}](
+				"delete_file",
+				"Delete a file",
+				func(_ context.Context, _ struct{}) (agent.ToolResult, error) {
+					t.Fatal("tool should not be called")
+					return agent.ToolResult{}, nil
+				},
+			)
+
+			innerProvider := &mockProvider{
+				responses: []*llm.ChatCompletionResponse{
+					toolCallResponse(llm.ToolCall{
+						ID:       "inner_tc1",
+						Function: llm.FunctionCall{Name: "delete_file", Arguments: `{}`},
+					}),
+					stopResponse("OK, I won't delete the file."),
+				},
+			}
+
+			innerAgent := agent.New(
+				"file_manager",
+				newTestClient(innerProvider),
+				agent.WithModel("test-model"),
+				agent.WithTools(deleteTool),
+				agent.WithApproval(agent.ApprovalConfig{
+					ToolNames: []string{"delete_file"},
+				}),
+			)
+
+			outerProvider := &mockProvider{
+				responses: []*llm.ChatCompletionResponse{
+					toolCallResponse(llm.ToolCall{
+						ID:       "outer_tc1",
+						Function: llm.FunctionCall{Name: "file_expert", Arguments: `{"input":"delete the file"}`},
+					}),
+					stopResponse("The file manager declined."),
+				},
+			}
+
+			outerAgent := agent.New(
+				"assistant",
+				newTestClient(outerProvider),
+				agent.WithModel("test-model"),
+				agent.WithTools(innerAgent.AsTool("file_expert", "Manage files")),
+			)
+
+			_, err := outerAgent.Run(
+				context.Background(),
+				[]llm.Message{userMessage("Delete the file")},
+			)
+
+			var interrupted *agent.InterruptedError
+			require.ErrorAs(t, err, &interrupted)
+
+			result, err := agent.Resume(
+				context.Background(),
+				interrupted,
+				agent.ResumeInput{
+					Approvals: map[string]agent.ApprovalResult{
+						"inner_tc1": {Approved: false, Message: "User denied deletion."},
+					},
+				},
+			)
+
+			require.NoError(t, err)
+			assert.Equal(t, "The file manager declined.", result.FinalMessage().Text())
+			assert.Equal(t, "assistant", result.LastAgent.Name())
+		},
+	)
+
+	t.Run(
+		"nested agent approval with parallel sibling tools",
+		func(t *testing.T) {
+			t.Parallel()
+
+			var siblingCalled bool
+
+			type Params struct{}
+			siblingTool := agent.FunctionTool[Params](
+				"list_files",
+				"List files",
+				func(_ context.Context, _ Params) (agent.ToolResult, error) {
+					siblingCalled = true
+					return agent.ToolResult{Content: "file1.txt, file2.txt"}, nil
+				},
+			)
+
+			deleteTool := agent.FunctionTool[struct{}](
+				"delete_file",
+				"Delete a file",
+				func(_ context.Context, _ struct{}) (agent.ToolResult, error) {
+					return agent.ToolResult{Content: "file deleted"}, nil
+				},
+			)
+
+			innerProvider := &mockProvider{
+				responses: []*llm.ChatCompletionResponse{
+					toolCallResponse(llm.ToolCall{
+						ID:       "inner_tc1",
+						Function: llm.FunctionCall{Name: "delete_file", Arguments: `{}`},
+					}),
+					stopResponse("File has been deleted."),
+				},
+			}
+
+			innerAgent := agent.New(
+				"file_manager",
+				newTestClient(innerProvider),
+				agent.WithModel("test-model"),
+				agent.WithTools(deleteTool),
+				agent.WithApproval(agent.ApprovalConfig{
+					ToolNames: []string{"delete_file"},
+				}),
+			)
+
+			outerProvider := &mockProvider{
+				responses: []*llm.ChatCompletionResponse{
+					toolCallResponse(
+						llm.ToolCall{
+							ID:       "outer_tc1",
+							Function: llm.FunctionCall{Name: "list_files", Arguments: `{}`},
+						},
+						llm.ToolCall{
+							ID:       "outer_tc2",
+							Function: llm.FunctionCall{Name: "file_expert", Arguments: `{"input":"delete the file"}`},
+						},
+					),
+					stopResponse("Files listed and deleted."),
+				},
+			}
+
+			outerAgent := agent.New(
+				"assistant",
+				newTestClient(outerProvider),
+				agent.WithModel("test-model"),
+				agent.WithTools(
+					siblingTool,
+					innerAgent.AsTool("file_expert", "Manage files"),
+				),
+			)
+
+			_, err := outerAgent.Run(
+				context.Background(),
+				[]llm.Message{userMessage("List and delete files")},
+			)
+
+			var interrupted *agent.InterruptedError
+			require.ErrorAs(t, err, &interrupted)
+			assert.True(t, siblingCalled)
+
+			result, err := agent.Resume(
+				context.Background(),
+				interrupted,
+				agent.ResumeInput{
+					Approvals: map[string]agent.ApprovalResult{
+						"inner_tc1": {Approved: true},
+					},
+				},
+			)
+
+			require.NoError(t, err)
+			assert.Equal(t, "Files listed and deleted.", result.FinalMessage().Text())
+		},
+	)
+
+	t.Run(
+		"three-level nesting A to B to C preserves full chain",
+		func(t *testing.T) {
+			t.Parallel()
+
+			var toolExecuted bool
+
+			dangerTool := agent.FunctionTool[struct{}](
+				"danger",
+				"Dangerous operation",
+				func(_ context.Context, _ struct{}) (agent.ToolResult, error) {
+					toolExecuted = true
+					return agent.ToolResult{Content: "danger executed"}, nil
+				},
+			)
+
+			cProvider := &mockProvider{
+				responses: []*llm.ChatCompletionResponse{
+					toolCallResponse(llm.ToolCall{
+						ID:       "c_tc1",
+						Function: llm.FunctionCall{Name: "danger", Arguments: `{}`},
+					}),
+					stopResponse("C done."),
+				},
+			}
+
+			agentC := agent.New(
+				"agent_c",
+				newTestClient(cProvider),
+				agent.WithModel("test-model"),
+				agent.WithTools(dangerTool),
+				agent.WithApproval(agent.ApprovalConfig{
+					ToolNames: []string{"danger"},
+				}),
+			)
+
+			bProvider := &mockProvider{
+				responses: []*llm.ChatCompletionResponse{
+					toolCallResponse(llm.ToolCall{
+						ID:       "b_tc1",
+						Function: llm.FunctionCall{Name: "call_c", Arguments: `{"input":"do danger"}`},
+					}),
+					stopResponse("B done."),
+				},
+			}
+
+			agentB := agent.New(
+				"agent_b",
+				newTestClient(bProvider),
+				agent.WithModel("test-model"),
+				agent.WithTools(agentC.AsTool("call_c", "Call agent C")),
+			)
+
+			aProvider := &mockProvider{
+				responses: []*llm.ChatCompletionResponse{
+					toolCallResponse(llm.ToolCall{
+						ID:       "a_tc1",
+						Function: llm.FunctionCall{Name: "call_b", Arguments: `{"input":"delegate to C"}`},
+					}),
+					stopResponse("A done."),
+				},
+			}
+
+			agentA := agent.New(
+				"agent_a",
+				newTestClient(aProvider),
+				agent.WithModel("test-model"),
+				agent.WithTools(agentB.AsTool("call_b", "Call agent B")),
+			)
+
+			_, err := agentA.Run(
+				context.Background(),
+				[]llm.Message{userMessage("start")},
+			)
+
+			require.Error(t, err)
+			var interrupted *agent.InterruptedError
+			require.ErrorAs(t, err, &interrupted)
+			assert.Equal(t, "agent_c", interrupted.Agent.Name())
+			assert.Equal(t, "danger", interrupted.PendingApprovals[0].Function.Name)
+			assert.False(t, toolExecuted)
+
+			result, err := agent.Resume(
+				context.Background(),
+				interrupted,
+				agent.ResumeInput{
+					Approvals: map[string]agent.ApprovalResult{
+						"c_tc1": {Approved: true},
+					},
+				},
+			)
+
+			require.NoError(t, err)
+			assert.True(t, toolExecuted)
+			assert.Equal(t, "A done.", result.FinalMessage().Text())
+			assert.Equal(t, "agent_a", result.LastAgent.Name())
+		},
+	)
+}
+
 func TestAgentTool_InterfaceSatisfaction(t *testing.T) {
 	t.Parallel()
 
diff --git a/pkg/agent/errors.go b/pkg/agent/errors.go
index df59c79b3..595597f3f 100644
--- a/pkg/agent/errors.go
+++ b/pkg/agent/errors.go
@@ -42,12 +42,37 @@ type (
 		Messages         []llm.Message
 		Usage            llm.Usage
 		Turns            int
+
+		outerState *outerLoopState
 	}
 
 	needsApprovalError struct {
 		allToolCalls     []llm.ToolCall
 		pendingApprovals []llm.ToolCall
 	}
+
+	nestedInterruptionError struct {
+		inner          *InterruptedError
+		toolCallID     string
+		allToolCalls   []llm.ToolCall
+		completedCalls []completedCall
+	}
+
+	outerLoopState struct {
+		agent          *Agent
+		messages       []llm.Message
+		usage          llm.Usage
+		turns          int
+		allToolCalls   []llm.ToolCall
+		toolCallID     string
+		completedCalls []completedCall
+		innerInterrupt *InterruptedError
+	}
+
+	completedCall struct {
+		toolCallID string
+		result     ToolResult
+	}
 )
 
 func (e *MaxTurnsExceededError) Error() string {
@@ -69,3 +94,7 @@ func (e *InterruptedError) Error() string {
 func (e *needsApprovalError) Error() string {
 	return fmt.Sprintf("%d tool call(s) require approval", len(e.pendingApprovals))
 }
+
+func (e *nestedInterruptionError) Error() string {
+	return fmt.Sprintf("nested agent interrupted: %s", e.inner.Error())
+}
diff --git a/pkg/agent/run.go b/pkg/agent/run.go
index a0df7cbe9..17d6c7f47 100644
--- a/pkg/agent/run.go
+++ b/pkg/agent/run.go
@@ -396,6 +396,42 @@ func coreLoop(ctx context.Context, startAgent *Agent, inputMessages []llm.Messag
 						},
 					)
 				}
+
+				if nie, ok := errors.AsType[*nestedInterruptionError](err); ok {
+					s.logger.InfoCtx(
+						ctx,
+						"nested agent interrupted, approval required",
+						log.Int("pending_count", len(nie.inner.PendingApprovals)),
+						log.String("nested_agent", nie.inner.Agent.name),
+					)
+
+					msgsCopy := make([]llm.Message, len(s.messages))
+					copy(msgsCopy, s.messages)
+
+					return s.finishRun(
+						ctx,
+						nil,
+						&InterruptedError{
+							ToolCalls:        nie.inner.ToolCalls,
+							PendingApprovals: nie.inner.PendingApprovals,
+							Agent:            nie.inner.Agent,
+							Messages:         nie.inner.Messages,
+							Usage:            nie.inner.Usage,
+							Turns:            nie.inner.Turns,
+							outerState: &outerLoopState{
+								agent:          s.agent,
+								messages:       msgsCopy,
+								usage:          s.totalUsage,
+								turns:          s.turns,
+								allToolCalls:   nie.allToolCalls,
+								toolCallID:     nie.toolCallID,
+								completedCalls: nie.completedCalls,
+								innerInterrupt: nie.inner,
+							},
+						},
+					)
+				}
+
 				return s.finishRun(ctx, nil, err)
 			}
 
@@ -553,6 +589,24 @@ func executeWithHandoff(
 
 		tr, err := executeSingleTool(ctx, tracer, agent, toolCalls[i], descriptors[i].(Tool), onEvent, logger)
 		if err != nil {
+			if ie, ok := errors.AsType[*InterruptedError](err); ok {
+				var completed []completedCall
+				for j := range results {
+					completed = append(
+						completed,
+						completedCall{
+							toolCallID: toolCalls[j].ID,
+							result:     results[j].Result,
+						},
+					)
+				}
+				return nil, nil, msgs, &nestedInterruptionError{
+					inner:          ie,
+					toolCallID:     toolCalls[i].ID,
+					allToolCalls:   toolCalls,
+					completedCalls: completed,
+				}
+			}
 			return nil, nil, msgs, err
 		}
 
@@ -622,6 +676,44 @@ func executeParallel(
 
 	wg.Wait()
 
+	for i, entry := range entries {
+		var ie *InterruptedError
+		if entry.err != nil && errors.As(entry.err, &ie) {
+			var completed []completedCall
+			for j, other := range entries {
+				if j == i {
+					continue
+				}
+				if other.err != nil {
+					completed = append(
+						completed,
+						completedCall{
+							toolCallID: toolCalls[j].ID,
+							result: ToolResult{
+								Content: fmt.Sprintf("Error: %s", other.err.Error()),
+								IsError: true,
+							},
+						},
+					)
+					continue
+				}
+				completed = append(
+					completed,
+					completedCall{
+						toolCallID: toolCalls[j].ID,
+						result:     other.result,
+					},
+				)
+			}
+			return nil, nil, &nestedInterruptionError{
+				inner:          ie,
+				toolCallID:     toolCalls[i].ID,
+				allToolCalls:   toolCalls,
+				completedCalls: completed,
+			}
+		}
+	}
+
 	var (
 		results []ToolCallResult
 		msgs    []llm.Message
@@ -710,6 +802,12 @@ func executeSingleTool(
 
 	result, err := tool.Execute(toolCtx, tc.Function.Arguments)
 	if err != nil {
+		if _, ok := errors.AsType[*InterruptedError](err); ok {
+			toolSpan.SetAttributes(attribute.Bool("tool.interrupted", true))
+			toolSpan.End()
+			return ToolResult{}, err
+		}
+
 		toolSpan.RecordError(err)
 		toolSpan.SetStatus(codes.Error, err.Error())
 		toolSpan.End()
@@ -812,6 +910,10 @@ func runOutputGuardrails(ctx context.Context, agent *Agent, message llm.Message)
 // are not re-evaluated because the messages were already validated in the
 // original Run call.
 func Resume(ctx context.Context, interrupted *InterruptedError, input ResumeInput) (*Result, error) {
+	if interrupted.outerState != nil {
+		return resumeNested(ctx, interrupted, input)
+	}
+
 	tracer := otel.GetTracerProvider().Tracer(tracerName)
 	logger := interrupted.Agent.logger
 
@@ -965,6 +1067,86 @@ func Resume(ctx context.Context, interrupted *InterruptedError, input ResumeInpu
 	)
 }
 
+func resumeNested(ctx context.Context, interrupted *InterruptedError, input ResumeInput) (*Result, error) {
+	outer := interrupted.outerState
+	logger := outer.agent.logger
+
+	logger.InfoCtx(
+		ctx,
+		"resuming nested agent interruption",
+		log.String("outer_agent", outer.agent.name),
+		log.String("inner_agent", interrupted.Agent.name),
+	)
+
+	innerResult, err := Resume(ctx, outer.innerInterrupt, input)
+	if err != nil {
+		var innerIE *InterruptedError
+		if errors.As(err, &innerIE) {
+			return nil, &InterruptedError{
+				ToolCalls:        innerIE.ToolCalls,
+				PendingApprovals: innerIE.PendingApprovals,
+				Agent:            innerIE.Agent,
+				Messages:         innerIE.Messages,
+				Usage:            innerIE.Usage,
+				Turns:            innerIE.Turns,
+				outerState: &outerLoopState{
+					agent:          outer.agent,
+					messages:       outer.messages,
+					usage:          outer.usage,
+					turns:          outer.turns,
+					allToolCalls:   outer.allToolCalls,
+					toolCallID:     outer.toolCallID,
+					completedCalls: outer.completedCalls,
+					innerInterrupt: innerIE,
+				},
+			}
+		}
+		return nil, fmt.Errorf("cannot resume nested agent: %w", err)
+	}
+
+	completedMap := make(map[string]ToolResult, len(outer.completedCalls))
+	for _, cc := range outer.completedCalls {
+		completedMap[cc.toolCallID] = cc.result
+	}
+
+	messages := make([]llm.Message, len(outer.messages))
+	copy(messages, outer.messages)
+
+	for _, tc := range outer.allToolCalls {
+		var content string
+		if tc.ID == outer.toolCallID {
+			content = innerResult.FinalMessage().Text()
+		} else if cr, ok := completedMap[tc.ID]; ok {
+			content = cr.Content
+		} else {
+			content = "Error: tool execution was interrupted"
+		}
+
+		messages = append(
+			messages,
+			llm.Message{
+				Role:       llm.RoleTool,
+				ToolCallID: tc.ID,
+				Parts:      []llm.Part{llm.TextPart{Text: content}},
+			},
+		)
+	}
+
+	return coreLoop(
+		ctx,
+		outer.agent,
+		messages,
+		runOpts{
+			callLLM:             blockingCallLLM,
+			onEvent:             noopEvent,
+			skipInputGuardrails: true,
+			skipSessionLoad:     true,
+			initialUsage:        outer.usage,
+			initialTurns:        outer.turns,
+		},
+	)
+}
+
 func emitHook(agent *Agent, fn func(RunHooks)) {
 	for _, h := range agent.hooks {
 		fn(h)