diff --git a/server/ask_operator.go b/server/ask_operator.go
new file mode 100644
index 0000000..4780146
--- /dev/null
+++ b/server/ask_operator.go
@@ -0,0 +1,118 @@
+package server
+
+import (
+	"context"
+	"encoding/json"
+	"fmt"
+	"io"
+	"os"
+	"path/filepath"
+	"strings"
+	"time"
+
+	"github.com/Autumn-27/artex/agent"
+	actool "github.com/Autumn-27/norma/tool"
+)
+
+const askOperatorMaxImage = 10 << 20
+
+var askOperatorImageExt = map[string]bool{".png": true, ".jpg": true, ".jpeg": true, ".webp": true, ".gif": true}
+
+// toolAskOperator lets a worker formally request operator input (captcha, OTP,
+// 2FA, a decision): the question and an optional screenshot land in the intent's
+// transcript as a user-role turn with an attachment card, and the intent pauses.
+// The operator replies through the existing message-to-worker flow; the reply
+// resumes the run with the answer as the next input (#41).
+func (s *Server) toolAskOperator() actool.CoreTool {
+	return wrTool("ask_operator",
+		"Ask the human operator for input you cannot obtain yourself (a captcha solution, an email/SMS OTP code, a 2FA answer, a decision). The question appears in this intent's chat for the operator, optionally with a screenshot, and this intent then pauses; the operator's reply resumes this run with the answer as your next input. Ask precisely, and only when you are genuinely blocked.",
+		map[string]any{
+			"type": "object",
+			"properties": map[string]any{
+				"question": map[string]any{
+					"type":        "string",
+					"description": "What you need from the operator, precisely (e.g. 'enter the 6-digit code sent to x@y', 'solve the captcha in the attached screenshot').",
+				},
+				"image_path": map[string]any{
+					"type":        "string",
+					"description": "Optional path to a screenshot (png/jpg/jpeg/webp/gif, max 10MB), e.g. the browser_take_screenshot output. It is copied into the task uploads and shown to the operator.",
+				},
+			},
+			"required": []any{"question"},
+		},
+		func(ctx context.Context, in json.RawMessage) (actool.Result, error) {
+			var req struct {
+				Question  string `json:"question"`
+				ImagePath string `json:"image_path"`
+			}
+			_ = json.Unmarshal(in, &req)
+			q := strings.TrimSpace(req.Question)
+			if q == "" {
+				return actool.Errorf("Error: question is required"), nil
+			}
+			ri := agent.RunInfoFrom(ctx)
+			if ri.TaskID == 0 || ri.IntentID == 0 {
+				return actool.Errorf("Error: ask_operator can only be used inside a worker intent run"), nil
+			}
+			taskID := fmt.Sprintf("%d", ri.TaskID)
+			t := s.m.ResolveTask(taskID)
+			if t == nil {
+				return actool.Errorf("Error: task not found"), nil
+			}
+			att, err := stageAskOperatorImage(s.m.dir, taskID, req.ImagePath)
+			if err != nil {
+				return actool.Errorf("Error: " + err.Error()), nil
+			}
+			text := "OPERATOR INPUT REQUESTED: " + q + " (this intent is pausing; reply here to resume it with your answer)"
+			act := userActivityWithAttachments("worker", text, att)
+			node := ri.IntentID
+			act.NodeID = &node
+			s.engine.emitActivity(t, act)
+			// The control call runs on a detached context: pausing may cancel the
+			// run's context, and the pause bookkeeping itself must complete.
+			if _, err := s.applyIntentControl(context.Background(), t, ri.IntentID, "pause", firstLine(q, 120), ""); err != nil {
+				return actool.Errorf("Error: question delivered but pausing the intent failed: " + err.Error()), nil
+			}
+			return actool.Text("Question delivered to the operator. This intent is pausing now: finish your current step, record everything you already know as facts, and stop. The operator's reply will resume this run and arrive as your next input."), nil
+		})
+}
+
+// stageAskOperatorImage copies the referenced image into the task's uploads dir
+// (the same place chat uploads land, so the transcript attachment card resolves)
+// and returns the attachment descriptor. Empty src returns no attachment.
+func stageAskOperatorImage(dataDir, taskID, src string) ([]chatAttachment, error) {
+	src = strings.TrimSpace(src)
+	if src == "" {
+		return nil, nil
+	}
+	ext := strings.ToLower(filepath.Ext(src))
+	if !askOperatorImageExt[ext] {
+		return nil, fmt.Errorf("image_path must be a png/jpg/jpeg/webp/gif file, got %q", filepath.Base(src))
+	}
+	st, err := os.Stat(src)
+	if err != nil {
+		return nil, fmt.Errorf("image not readable: %v", err)
+	}
+	if st.Size() > askOperatorMaxImage {
+		return nil, fmt.Errorf("image too large (%s, max 10MB)", humanBytes(st.Size()))
+	}
+	dir := filepath.Join(dataDir, "tasks", taskID, "uploads")
+	if err := os.MkdirAll(dir, 0o755); err != nil {
+		return nil, err
+	}
+	name := fmt.Sprintf("ask-operator-%d%s", time.Now().Unix(), ext)
+	in, err := os.Open(src)
+	if err != nil {
+		return nil, err
+	}
+	defer in.Close()
+	out, err := os.Create(filepath.Join(dir, name))
+	if err != nil {
+		return nil, err
+	}
+	defer out.Close()
+	if _, err := io.Copy(out, in); err != nil {
+		return nil, err
+	}
+	return []chatAttachment{{Name: name, Path: "uploads/" + name, Size: st.Size()}}, nil
+}
diff --git a/server/ask_operator_test.go b/server/ask_operator_test.go
new file mode 100644
index 0000000..7447e00
--- /dev/null
+++ b/server/ask_operator_test.go
@@ -0,0 +1,70 @@
+package server
+
+import (
+	"encoding/json"
+	"os"
+	"path/filepath"
+	"strings"
+	"testing"
+)
+
+func TestStageAskOperatorImage(t *testing.T) {
+	dir := t.TempDir()
+	src := filepath.Join(dir, "shot.png")
+	if err := os.WriteFile(src, []byte("fakepng"), 0o644); err != nil {
+		t.Fatal(err)
+	}
+
+	// no image -> no attachment
+	att, err := stageAskOperatorImage(dir, "7", "")
+	if err != nil || att != nil {
+		t.Fatalf("empty src: att=%v err=%v", att, err)
+	}
+
+	// valid image -> copied under the task uploads, descriptor matches the chat format
+	att, err = stageAskOperatorImage(dir, "7", src)
+	if err != nil || len(att) != 1 {
+		t.Fatalf("valid src: att=%v err=%v", att, err)
+	}
+	if !strings.HasPrefix(att[0].Path, "uploads/ask-operator-") || !strings.HasSuffix(att[0].Path, ".png") {
+		t.Fatalf("unexpected attachment path %q", att[0].Path)
+	}
+	if _, err := os.Stat(filepath.Join(dir, "tasks", "7", "uploads", att[0].Name)); err != nil {
+		t.Fatalf("copy missing: %v", err)
+	}
+
+	// wrong extension rejected
+	bad := filepath.Join(dir, "payload.exe")
+	if err := os.WriteFile(bad, []byte("x"), 0o644); err != nil {
+		t.Fatal(err)
+	}
+	if _, err := stageAskOperatorImage(dir, "7", bad); err == nil || !strings.Contains(err.Error(), "png/jpg") {
+		t.Fatalf("expected extension rejection, got %v", err)
+	}
+
+	// missing file rejected
+	if _, err := stageAskOperatorImage(dir, "7", filepath.Join(dir, "nope.png")); err == nil {
+		t.Fatal("expected missing-file rejection")
+	}
+}
+
+// The emitted activity must carry the {text, attachments} Detail shape the
+// transcript parser expects, so the operator sees the question with the
+// attachment card for the screenshot.
+func TestAskOperatorActivityShape(t *testing.T) {
+	att := []chatAttachment{{Name: "ask-operator-1.png", Path: "uploads/ask-operator-1.png", Size: 7}}
+	a := userActivityWithAttachments("worker", "OPERATOR INPUT REQUESTED: solve the captcha", att)
+	if a.Kind != "user" || a.Worker != "worker" {
+		t.Fatalf("unexpected activity kind/worker: %+v", a)
+	}
+	var parsed struct {
+		Text        string           `json:"text"`
+		Attachments []chatAttachment `json:"attachments"`
+	}
+	if err := json.Unmarshal([]byte(a.Detail), &parsed); err != nil {
+		t.Fatal(err)
+	}
+	if !strings.HasPrefix(parsed.Text, "OPERATOR INPUT REQUESTED") || len(parsed.Attachments) != 1 || parsed.Attachments[0].Path != att[0].Path {
+		t.Fatalf("unexpected detail payload: %+v", parsed)
+	}
+}
diff --git a/server/orchestration.go b/server/orchestration.go
index 2251a2c..694b6af 100644
--- a/server/orchestration.go
+++ b/server/orchestration.go
@@ -489,6 +489,10 @@ func (s *Server) seedOrchestrationTools() {
 			// health visibility is for the executors too, not just the platform agent
 			bindings = json.RawMessage(`["auto","worker","pentest"]`)
 		}
+		if t.Name() == "ask_operator" {
+			// operator input requests are an executor concern (captcha/OTP walls)
+			bindings = json.RawMessage(`["worker","pentest"]`)
+		}
 		_ = s.m.PG().SeedTool(t.Name(), t.Description(), schema, bindings)
 	}
 	s.refreshBuiltinToolSchemas()
diff --git a/server/platform_tools.go b/server/platform_tools.go
index f37cef6..7ebde5e 100644
--- a/server/platform_tools.go
+++ b/server/platform_tools.go
@@ -19,6 +19,7 @@ import (
 func (s *Server) platformTools() []actool.CoreTool {
 	return []actool.CoreTool{
 		s.toolMCPStatus(),
+		s.toolAskOperator(),
 		s.toolCreateSkill(),
 		s.toolUpdateSkillFile(),
 		s.toolCreateCustomTool(),