diff --git a/apps/extension/src/tools/__tests__/fill.test.ts b/apps/extension/src/tools/__tests__/fill.test.ts
new file mode 100644
index 0000000..c7dba29
--- /dev/null
+++ b/apps/extension/src/tools/__tests__/fill.test.ts
@@ -0,0 +1,573 @@
+import { afterEach, describe, expect, it, vi } from "vitest";
+import { SessionManager } from "@/session-manager/manager";
+import type { CdpRunner } from "@/tools/shared";
+import { handleFill } from "../interaction";
+
+interface ScriptParams {
+  functionDeclaration: string;
+  arguments?: Array<{ value: unknown }>;
+}
+
+async function setup(markup = '<input value="old">') {
+  document.body.innerHTML = markup;
+  const element = document.body.firstElementChild as HTMLInputElement;
+  const manager = new SessionManager({
+    agentWindow: {
+      create: async () => 100,
+      remove: async () => {},
+      ensureActiveTab: async () => 4,
+    },
+  });
+  const ctx = await manager.start("aa11");
+  ctx.refStore.set("e1", 12, { tabId: 4 });
+  const script = vi.fn(async (params: ScriptParams): Promise<unknown> => {
+    try {
+      const fn = new Function(`return (${params.functionDeclaration})`)();
+      return {
+        result: {
+          value: await fn.apply(
+            element,
+            (params.arguments ?? []).map((arg) => arg.value),
+          ),
+        },
+      };
+    } catch {
+      return { exceptionDetails: { text: "test page script failed" } };
+    }
+  });
+  // Number/email controls have a browser caret even though their selection
+  // getters return null. Model that caret instead of assuming it is at the end.
+  const hiddenCaret = { start: 0, end: 0 };
+  const moveToEnd = vi.fn(async () => {
+    if (typeof element.selectionStart === "number") {
+      element.setSelectionRange(element.value.length, element.value.length);
+    } else {
+      hiddenCaret.start = hiddenCaret.end = element.value.length;
+    }
+  });
+  const insert = vi.fn(async (text: string) => {
+    const focused = document.activeElement as HTMLInputElement;
+    if (focused.readOnly || focused.disabled) return;
+    const start = focused.selectionStart ?? hiddenCaret.start;
+    const end = focused.selectionEnd ?? hiddenCaret.end;
+    const value = focused.value.slice(0, start) + text + focused.value.slice(end);
+    focused.value = focused.maxLength >= 0 ? value.slice(0, focused.maxLength) : value;
+    hiddenCaret.start = hiddenCaret.end = Math.min(start + text.length, focused.value.length);
+    focused.dispatchEvent(new Event("input", { bubbles: true }));
+  });
+  const release = vi.fn(async () => ({}));
+  const send = vi.fn(async (_tabId: number, method: string, params?: object) => {
+    switch (method) {
+      case "DOM.describeNode":
+        return {
+          node: {
+            nodeName: element.tagName,
+            attributes: Array.from(element.attributes).flatMap((attr) => [attr.name, attr.value]),
+          },
+        };
+      case "DOM.scrollIntoViewIfNeeded":
+        return {};
+      case "DOM.focus":
+        element.focus();
+        return {};
+      case "DOM.resolveNode":
+        return { object: { objectId: "fill-target" } };
+      case "Runtime.callFunctionOn":
+        return script(params as ScriptParams);
+      case "Input.insertText":
+        await insert((params as { text: string }).text);
+        return {};
+      case "Input.dispatchKeyEvent":
+        if ((params as { commands?: string[] }).commands?.includes("moveToEndOfDocument")) {
+          await moveToEnd();
+        }
+        return {};
+      case "Runtime.releaseObject":
+        return release();
+      default:
+        throw new Error(`unexpected ${method}`);
+    }
+  });
+  return {
+    element,
+    hiddenCaret,
+    moveToEnd,
+    script,
+    insert,
+    release,
+    send,
+    fill: (value = "hello", clearBefore = true, signal?: AbortSignal) =>
+      handleFill(
+        manager,
+        { session_id: "aa11", ref: "e1", value, clear_before: clearBefore },
+        {
+          cdp: { send: send as CdpRunner["send"] },
+          tabsApi: {
+            get: async (id) => ({ id, windowId: 100, active: true }) as chrome.tabs.Tab,
+            query: async () => [{ id: 4, windowId: 100, active: true } as chrome.tabs.Tab],
+          },
+          signal,
+        },
+      ),
+  };
+}
+
+afterEach(() => {
+  vi.restoreAllMocks();
+  document.body.innerHTML = "";
+});
+
+describe("fill result verification", () => {
+  it.each([
+    "readonly",
+    "disabled",
+  ])("preserves a %s field before rejecting it", async (attribute) => {
+    const h = await setup(`<input ${attribute} value="old">`);
+    expect(await h.fill()).toMatchObject({
+      code: "invalid_params",
+      data: { reason: "target_not_fillable" },
+    });
+    expect(h.element.value).toBe("old");
+    expect(h.insert).not.toHaveBeenCalled();
+    expect(h.release).toHaveBeenCalledOnce();
+  });
+
+  it.each([
+    "checkbox",
+    "radio",
+    "range",
+    "date",
+    "file",
+  ])("rejects an unsupported %s input before clearing", async (type) => {
+    const h = await setup(`<input type="${type}">`);
+    const before = h.element.value;
+    expect(await h.fill()).toMatchObject({
+      code: "invalid_params",
+      data: { reason: "target_not_fillable" },
+    });
+    expect(h.element.value).toBe(before);
+    expect(h.insert).not.toHaveBeenCalled();
+  });
+
+  it("rejects an overlong value before clearing", async () => {
+    const h = await setup('<input maxlength="3" value="old">');
+    expect(await h.fill()).toMatchObject({
+      code: "invalid_params",
+      message: /maxlength/,
+      data: { reason: "fill_value_invalid" },
+    });
+    expect(h.element.value).toBe("old");
+    expect(h.insert).not.toHaveBeenCalled();
+  });
+
+  it.each([
+    true,
+    false,
+  ])("classifies a DOM.focus rejection on a disabled=%s target", async (disabled) => {
+    const h = await setup(`<input ${disabled ? "disabled" : ""} value="old">`);
+    const send = h.send.getMockImplementation()!;
+    h.send.mockImplementation(async (tabId, method, params) => {
+      if (method === "DOM.focus") throw new Error("Element is not focusable");
+      return send(tabId, method, params);
+    });
+    expect(await h.fill()).toMatchObject({
+      code: disabled ? "invalid_params" : "cdp_failed",
+      data: { reason: disabled ? "target_not_fillable" : "fill_failed" },
+    });
+    expect(h.element.value).toBe("old");
+    expect(h.insert).not.toHaveBeenCalled();
+    expect(h.release).toHaveBeenCalledOnce();
+  });
+
+  it("fills a background document without requiring foreground browser focus", async () => {
+    const h = await setup();
+    vi.spyOn(document, "hasFocus").mockReturnValue(false);
+    expect(await h.fill()).toMatchObject({ value_length: 5 });
+    expect(h.element.value).toBe("hello");
+  });
+
+  it("restores focus once after clearing without typing into another field", async () => {
+    const h = await setup();
+    const other = document.createElement("input");
+    document.body.append(other);
+    h.element.addEventListener("input", () => other.focus());
+    expect(await h.fill()).toMatchObject({ value_length: 5 });
+    expect(h.element.value).toBe("hello");
+    expect(other.value).toBe("");
+    expect(h.send.mock.calls.filter(([, method]) => method === "DOM.focus")).toHaveLength(2);
+  });
+
+  it.each([
+    "focus",
+    "value",
+  ])("rechecks %s after restoring focus, without retrying again", async (action) => {
+    const h = await setup();
+    const other = document.createElement("input");
+    document.body.append(other);
+    h.element.addEventListener(
+      "input",
+      () => {
+        other.focus();
+        h.element.addEventListener("focus", () => {
+          if (action === "focus") queueMicrotask(() => other.focus());
+          else h.element.value = "changed";
+        });
+      },
+      { once: true },
+    );
+    expect(await h.fill()).toMatchObject({
+      code: "cdp_failed",
+      data: { reason: action === "focus" ? "fill_focus_lost" : "fill_target_changed" },
+    });
+    expect(other.value).toBe("");
+    expect(h.insert).not.toHaveBeenCalled();
+    expect(h.send.mock.calls.filter(([, method]) => method === "DOM.focus")).toHaveLength(2);
+  });
+
+  it.each([
+    "remove",
+    "readonly",
+    "restore",
+    "microtask-restore",
+  ])("stops when clearing causes the page to %s the target", async (action) => {
+    const h = await setup();
+    h.element.addEventListener("input", () => {
+      if (action === "remove") h.element.remove();
+      if (action === "readonly") h.element.readOnly = true;
+      if (action === "restore") h.element.value = "restored";
+      if (action === "microtask-restore")
+        queueMicrotask(() => {
+          h.element.value = "restored";
+        });
+    });
+    expect(await h.fill()).toMatchObject({
+      code: "cdp_failed",
+      data: { reason: "fill_target_changed" },
+    });
+    expect(h.insert).not.toHaveBeenCalled();
+  });
+
+  it("fails when insertText is acknowledged without changing the value", async () => {
+    const h = await setup();
+    h.insert.mockImplementation(async () => {});
+    expect(await h.fill()).toMatchObject({
+      code: "cdp_failed",
+      data: { reason: "fill_value_mismatch" },
+    });
+    expect(h.release).toHaveBeenCalledOnce();
+  });
+
+  it("detects truncation when maxlength changes after preparation", async () => {
+    const h = await setup();
+    h.element.addEventListener(
+      "input",
+      () => {
+        h.element.maxLength = 3;
+      },
+      { once: true },
+    );
+    expect(await h.fill()).toMatchObject({
+      code: "cdp_failed",
+      data: { reason: "fill_value_mismatch" },
+    });
+    expect(h.element.value).toBe("hel");
+  });
+
+  it.each([
+    "input",
+    "change",
+    "microtask-change",
+  ])("detects a value reverted by the %s handler", async (event) => {
+    const h = await setup();
+    h.element.addEventListener(event === "microtask-change" ? "change" : event, () => {
+      if (event === "microtask-change")
+        queueMicrotask(() => {
+          h.element.value = "";
+        });
+      else h.element.value = "";
+    });
+    expect(await h.fill()).toMatchObject({ code: "cdp_failed", message: /expected value/ });
+  });
+
+  it("compares content rather than length without including field values in the error", async () => {
+    const h = await setup('<input type="password">');
+    h.element.addEventListener("change", () => {
+      h.element.value = "other-secret";
+    });
+    const result = await h.fill("given-secret");
+    expect(result).toMatchObject({ code: "cdp_failed", message: /expected value/ });
+    expect(JSON.stringify(result)).not.toMatch(/given-secret|other-secret/);
+  });
+
+  it("does not report success for a target replaced by a change handler", async () => {
+    const h = await setup();
+    h.element.addEventListener("change", () => h.element.replaceWith(h.element.cloneNode()));
+    expect(await h.fill()).toMatchObject({
+      code: "cdp_failed",
+      data: { reason: "fill_target_changed" },
+    });
+  });
+
+  it.each([
+    1, 2, 3, 4, 5,
+  ])("rejects script exceptions at phase %s and releases the target", async (phase) => {
+    const h = await setup();
+    vi.spyOn(document, "hasFocus").mockReturnValue(false);
+    const run = h.script.getMockImplementation()!;
+    let count = 0;
+    h.script.mockImplementation(async (params) =>
+      ++count === phase ? { exceptionDetails: { text: "page secret" } } : run(params),
+    );
+    const result = await h.fill();
+    expect(result).toMatchObject({ code: "cdp_failed", data: { reason: "fill_failed" } });
+    expect(JSON.stringify(result)).not.toContain("page secret");
+    if (phase <= 3) expect(h.insert).not.toHaveBeenCalled();
+    expect(h.release).toHaveBeenCalledOnce();
+  });
+
+  it.each([1, 2, 3, 5])("rejects missing results at phase %s", async (phase) => {
+    const h = await setup();
+    vi.spyOn(document, "hasFocus").mockReturnValue(false);
+    const run = h.script.getMockImplementation()!;
+    let count = 0;
+    h.script.mockImplementation(async (params) =>
+      ++count === phase ? { result: { type: "undefined" } } : run(params),
+    );
+    expect(await h.fill()).toMatchObject({ code: "cdp_failed" });
+    if (phase <= 3) expect(h.insert).not.toHaveBeenCalled();
+  });
+
+  it.each(["input", "change"])("checks state after nested microtasks from %s", async (event) => {
+    const h = await setup();
+    h.element.addEventListener(event, () => {
+      queueMicrotask(() =>
+        queueMicrotask(() => {
+          h.element.value = "reverted";
+        }),
+      );
+    });
+    expect(await h.fill()).toMatchObject({ code: "cdp_failed" });
+    if (event === "input") expect(h.insert).not.toHaveBeenCalled();
+  });
+
+  it.each([
+    "<input>",
+    '<input type="password">',
+    "<textarea></textarea>",
+  ])("verifies successful text in %s", async (markup) => {
+    const h = await setup(markup);
+    expect(await h.fill("你好🙂")).toMatchObject({ value_length: 4 });
+    expect(h.element.value).toBe("你好🙂");
+    expect(h.release).toHaveBeenCalledOnce();
+  });
+
+  it("verifies append against the old value plus the requested text", async () => {
+    const h = await setup();
+    h.element.focus();
+    h.element.setSelectionRange(3, 3);
+    expect(await h.fill("!", false)).toMatchObject({ value_length: 4 });
+    expect(h.element.value).toBe("old!");
+  });
+
+  it.each([
+    ["<textarea></textarea>", "a\r\nb", "a\nb"],
+    ["<input>", "a\nb", "a b"],
+    ["<input>", "a\r\nb", "a b"],
+    [
+      '<input type="email" multiple>',
+      " a@example.com , b@example.com ",
+      "a@example.com,b@example.com",
+    ],
+  ])("accepts native normalization for %s", async (markup, requested, normalized) => {
+    if (markup.startsWith("<textarea")) {
+      // Happy DOM does not implement Chrome's textarea line-ending normalization.
+      const setter = Object.getOwnPropertyDescriptor(HTMLTextAreaElement.prototype, "value")!.set!;
+      vi.spyOn(HTMLTextAreaElement.prototype, "value", "set").mockImplementation(function (
+        this: HTMLTextAreaElement,
+        value,
+      ) {
+        setter.call(this, value.replace(/\r\n?/g, "\n"));
+      });
+    }
+    const h = await setup(markup);
+    h.insert.mockImplementation(async () => {
+      h.element.value = normalized;
+    });
+    expect(await h.fill(requested)).toMatchObject({ value_length: normalized.length });
+  });
+
+  it("does not count an editable padding break as an extra typed character", async () => {
+    const h = await setup('<div contenteditable="true" tabindex="0"></div>');
+    // These two layout/editability properties are missing in Happy DOM.
+    let innerText = "";
+    Object.defineProperty(h.element, "isContentEditable", { get: () => true });
+    Object.defineProperty(h.element, "innerText", { get: () => innerText });
+    h.insert.mockImplementation(async () => {
+      h.element.innerHTML = "one<div><br></div>";
+      innerText = "one\n\n";
+    });
+    expect(await h.fill("one\n")).toMatchObject({ value_length: 4 });
+  });
+
+  it.each([
+    [0, 0],
+    [1, 1],
+    [0, 3],
+  ])("appends after moving selection %s:%s to the end", async (start, end) => {
+    const h = await setup();
+    h.element.focus();
+    h.element.setSelectionRange(start, end);
+    expect(await h.fill("🙂", false)).toMatchObject({ value_length: 5 });
+    expect(h.element.value).toBe("old🙂");
+  });
+
+  it.each(
+    ["number", "email"].flatMap((type) =>
+      [
+        [0, 0],
+        [1, 1],
+        [0, 2],
+      ].map(([start, end]) => ({ type, start, end })),
+    ),
+  )("appends to $type from selection $start:$end without using its unsupported API", async ({
+    type,
+    start,
+    end,
+  }) => {
+    const h = await setup(`<input type="${type}" value="12">`);
+    Object.assign(h.hiddenCaret, { start, end });
+    vi.spyOn(h.element, "selectionStart", "get").mockReturnValue(null);
+    vi.spyOn(h.element, "selectionEnd", "get").mockReturnValue(null);
+    const selection = vi.spyOn(h.element, "setSelectionRange").mockImplementation(() => {
+      throw new DOMException("unsupported", "InvalidStateError");
+    });
+    expect(await h.fill("3", false)).toMatchObject({ value_length: 3 });
+    expect(h.element.value).toBe("123");
+    expect(selection).not.toHaveBeenCalled();
+  });
+
+  it.each([
+    "number",
+    "email",
+  ])("does not report successful %s append when the caret command is ignored", async (type) => {
+    const h = await setup(`<input type="${type}" value="12">`);
+    vi.spyOn(h.element, "selectionStart", "get").mockReturnValue(null);
+    vi.spyOn(h.element, "selectionEnd", "get").mockReturnValue(null);
+    h.moveToEnd.mockResolvedValueOnce(undefined);
+    expect(await h.fill("3", false)).toMatchObject({
+      code: "cdp_failed",
+      data: { reason: "fill_value_mismatch" },
+    });
+    expect(h.element.value).toBe("312");
+    expect(h.insert).toHaveBeenCalledOnce();
+  });
+
+  it("rejects invalid number text before clearing", async () => {
+    const h = await setup('<input type="number" value="12">');
+    expect(await h.fill("abc")).toMatchObject({
+      code: "invalid_params",
+      data: { reason: "fill_value_invalid" },
+    });
+    expect(h.element.value).toBe("12");
+    expect(h.insert).not.toHaveBeenCalled();
+  });
+
+  it("reports page formatting as unconfirmed without retrying the write", async () => {
+    const h = await setup();
+    h.element.addEventListener("change", () => {
+      h.element.value = h.element.value.toUpperCase();
+    });
+    expect(await h.fill()).toMatchObject({
+      code: "cdp_failed",
+      data: { reason: "fill_value_mismatch" },
+    });
+    expect(h.element.value).toBe("HELLO");
+    expect(h.insert).toHaveBeenCalledOnce();
+  });
+
+  it.each([
+    ["focus", false],
+    ["focus", true],
+    ["value", false],
+    ["value", true],
+    ["cancel", false],
+    ["cancel", true],
+    ["throw", false],
+    ["throw", true],
+  ] as const)("stops when positioning triggers %s (clear=%s) and releases the key", async (action, clearBefore) => {
+    const h = await setup();
+    vi.spyOn(document, "hasFocus").mockReturnValue(false);
+    const controller = new AbortController();
+    const other = document.createElement("input");
+    document.body.append(other);
+    const send = h.send.getMockImplementation()!;
+    h.send.mockImplementation(async (tabId, method, params) => {
+      const reply = await send(tabId, method, params);
+      if (
+        method === "Input.dispatchKeyEvent" &&
+        (params as { type: string }).type === "rawKeyDown"
+      ) {
+        if (action === "focus") other.focus();
+        if (action === "value") h.element.value = "changed";
+        if (action === "cancel") controller.abort();
+        if (action === "throw") throw new Error("dispatch failed");
+      }
+      return reply;
+    });
+    const result = await h.fill("!", clearBefore, controller.signal);
+    expect(result).toMatchObject({ code: action === "cancel" ? "cancelled" : "cdp_failed" });
+    expect(h.insert).not.toHaveBeenCalled();
+    expect(other.value).toBe("");
+    expect(h.send).toHaveBeenCalledWith(
+      4,
+      "Input.dispatchKeyEvent",
+      expect.objectContaining({ type: "keyUp" }),
+    );
+    expect(h.release).toHaveBeenCalledOnce();
+  });
+
+  it.each([true, false])("verifies an empty request with clear_before=%s", async (clearBefore) => {
+    const h = await setup();
+    expect(await h.fill("", clearBefore)).toMatchObject({ value_length: clearBefore ? 0 : 3 });
+    expect(h.element.value).toBe(clearBefore ? "" : "old");
+    expect(h.insert).not.toHaveBeenCalled();
+  });
+
+  it("cancels after insertion without sending change events", async () => {
+    const h = await setup();
+    const controller = new AbortController();
+    h.insert.mockImplementation(async () => controller.abort());
+    expect(await h.fill("hello", true, controller.signal)).toMatchObject({ code: "cancelled" });
+    expect(h.script).toHaveBeenCalledTimes(2);
+    expect(h.release).toHaveBeenCalledOnce();
+  });
+
+  it("cancels after resolving the remote object without clearing the field", async () => {
+    const h = await setup();
+    const controller = new AbortController();
+    const send = h.send.getMockImplementation()!;
+    h.send.mockImplementation(async (tabId, method, params) => {
+      const result = await send(tabId, method, params);
+      if (method === "DOM.resolveNode") controller.abort();
+      return result;
+    });
+    expect(await h.fill("hello", true, controller.signal)).toMatchObject({ code: "cancelled" });
+    expect(h.element.value).toBe("old");
+    expect(h.script).not.toHaveBeenCalled();
+    expect(h.release).toHaveBeenCalledOnce();
+  });
+
+  it("honors cancellation during verification", async () => {
+    const h = await setup();
+    const controller = new AbortController();
+    h.element.addEventListener("change", () => controller.abort());
+    expect(await h.fill("hello", true, controller.signal)).toMatchObject({ code: "cancelled" });
+    expect(h.release).toHaveBeenCalledOnce();
+  });
+
+  it("keeps the verified outcome when releasing the remote object fails", async () => {
+    const h = await setup();
+    h.release.mockRejectedValueOnce(new Error("target closed"));
+    expect(await h.fill()).toMatchObject({ value_length: 5 });
+  });
+});
diff --git a/apps/extension/src/tools/__tests__/interaction.test.ts b/apps/extension/src/tools/__tests__/interaction.test.ts
index 45ab74e..7cb1d4d 100644
--- a/apps/extension/src/tools/__tests__/interaction.test.ts
+++ b/apps/extension/src/tools/__tests__/interaction.test.ts
@@ -540,6 +540,21 @@ describe("handleHover", () => {
   });
 });
 
+function successfulFillScript(params: unknown) {
+  const script = params as { arguments?: Array<{ value: unknown }>; functionDeclaration: string };
+  const args = script.arguments ?? [];
+  return {
+    result: {
+      value:
+        args.length === 2
+          ? { before: "", expected: args[0].value }
+          : script.functionDeclaration.startsWith("function(expected)")
+            ? { connected: true, matches: true, valueLength: String(args[0].value).length }
+            : "ready",
+    },
+  };
+}
+
 describe("handleFill", () => {
   it("returns not_found for unknown ref", async () => {
     const sm = new SessionManager({ agentWindow: fakeAgentWindow([100]) });
@@ -586,7 +601,8 @@ describe("handleFill", () => {
       "DOM.scrollIntoViewIfNeeded": () => ({}),
       "DOM.focus": () => ({}),
       "DOM.resolveNode": () => ({ object: { objectId: "obj-1" } }),
-      "Runtime.callFunctionOn": () => ({ result: { type: "undefined" } }),
+      "Runtime.callFunctionOn": successfulFillScript,
+      "Runtime.releaseObject": () => ({}),
       "Input.insertText": () => ({}),
     });
     const res = await handleFill(
@@ -600,13 +616,12 @@ describe("handleFill", () => {
     expect(res.used_ref).toBe("e1");
     const insert = fake.sent.find((c) => c.method === "Input.insertText");
     expect(insert?.params).toEqual({ text: "hello" });
-    // clear_before defaults to true → callFunctionOn invoked once to
-    // clear, once to fire input/change after typing.
+    // Foreground replacement needs no extra caret-positioning round trip.
     const callFns = fake.sent.filter((c) => c.method === "Runtime.callFunctionOn");
-    expect(callFns.length).toBeGreaterThanOrEqual(2);
+    expect(callFns).toHaveLength(4);
   });
 
-  it("clear_before=false skips the wipe call", async () => {
+  it("passes clear_before=false to preparation and verifies the result", async () => {
     const sm = new SessionManager({ agentWindow: fakeAgentWindow([100]) });
     const ctx = await sm.start("aa11");
     ctx.refStore.set("e1", 1, { tabId: 4 });
@@ -618,12 +633,12 @@ describe("handleFill", () => {
       "DOM.focus": () => ({}),
       "DOM.resolveNode": () => ({ object: { objectId: "obj-2" } }),
       "Runtime.callFunctionOn": (p) => {
-        const fn = (p as { functionDeclaration?: string }).functionDeclaration ?? "";
-        // No "this.value = ''" clearing on a no-clear path; only the
-        // post-input dispatchEvent.
-        expect(fn).not.toMatch(/this\.value\s*=\s*''/);
-        return { result: { type: "undefined" } };
+        const args = (p as { arguments?: Array<{ value: unknown }> }).arguments ?? [];
+        if (args.length === 2) expect(args[1].value).toBe(false);
+        return successfulFillScript(p);
       },
+      "Input.dispatchKeyEvent": () => ({}),
+      "Runtime.releaseObject": () => ({}),
       "Input.insertText": () => ({}),
     });
     const res = await handleFill(
@@ -650,7 +665,8 @@ describe("handleFill", () => {
       "DOM.scrollIntoViewIfNeeded": () => ({}),
       "DOM.focus": () => ({}),
       "DOM.resolveNode": () => ({ object: { objectId: "obj-3" } }),
-      "Runtime.callFunctionOn": () => ({ result: { type: "undefined" } }),
+      "Runtime.callFunctionOn": successfulFillScript,
+      "Runtime.releaseObject": () => ({}),
       "Input.insertText": () => ({}),
     });
     const res = await handleFill(
diff --git a/apps/extension/src/tools/interaction.ts b/apps/extension/src/tools/interaction.ts
index 18608ca..9e36c2d 100644
--- a/apps/extension/src/tools/interaction.ts
+++ b/apps/extension/src/tools/interaction.ts
@@ -609,6 +609,53 @@ type SelectMutationResult =
 // tool.fill
 // ---------------------------------------------------------------------------
 
+type FillFailureReason =
+  | "target_not_fillable"
+  | "fill_value_invalid"
+  | "fill_target_changed"
+  | "fill_focus_lost"
+  | "fill_value_mismatch"
+  | "fill_failed";
+
+type FillPreparation =
+  | { before: string; expected: string }
+  | { reason: FillFailureReason; error: string };
+
+type FillReadiness = "ready" | "background" | "fill_target_changed" | "fill_focus_lost";
+
+function fillError(reason: FillFailureReason, message: string): RpcError {
+  return rpcError(
+    reason === "target_not_fillable" || reason === "fill_value_invalid"
+      ? "invalid_params"
+      : "cdp_failed",
+    reason,
+    message,
+  );
+}
+
+interface FillScriptReply<T> {
+  result?: { value?: T };
+  exceptionDetails?: unknown;
+}
+
+const FILL_EDITABLE_FUNCTION = `function() {
+  const tag = this.tagName.toLowerCase();
+  const supported = tag === 'input'
+    ? ['text', 'search', 'tel', 'url', 'email', 'password', 'number'].includes(this.type)
+    : tag === 'textarea' || this.isContentEditable;
+  return this.isConnected && supported && !this.readOnly && !this.matches(':disabled');
+}`;
+
+// Chrome renders a trailing editable newline with an empty <div><br></div>.
+// innerText includes the padding break; it is not an extra typed character.
+const FILL_VALUE_FUNCTION = `function() {
+  if (!this.isContentEditable) return this.value;
+  const value = this.innerText;
+  const tail = this.lastChild;
+  const padding = tail && tail.nodeName === 'DIV' && tail.childNodes.length === 1 && tail.firstChild.nodeName === 'BR';
+  return padding && value.endsWith('\\n\\n') ? value.slice(0, -1) : value;
+}`;
+
 export async function handleFill(
   manager: SessionManager,
   params: FillParams,
@@ -660,12 +707,8 @@ export async function handleFill(
     if (throwIfAborted(deps.signal)) {
       return { code: "cancelled", message: "fill aborted" };
     }
-    await nodeCdp.send(target.tabId, "DOM.focus", { backendNodeId: node.backendNodeId });
   } catch (err) {
-    return {
-      code: "cdp_failed",
-      message: err instanceof Error ? err.message : String(err),
-    };
+    return fillError("fill_failed", err instanceof Error ? err.message : String(err));
   }
 
   if (throwIfAborted(deps.signal)) {
@@ -678,57 +721,252 @@ export async function handleFill(
   const clearBefore = params.clear_before ?? true;
 
   try {
-    if (clearBefore) {
-      // Clear input/textarea value or wipe contenteditable innerText,
-      // then fire `input` so frameworks observe the empty state.
-      await nodeCdp.send(target.tabId, "Runtime.callFunctionOn", {
-        objectId,
-        functionDeclaration: `function() {
-          if (this.isContentEditable) { this.textContent = ''; }
-          else {
-            const proto = this instanceof HTMLTextAreaElement
-              ? HTMLTextAreaElement.prototype
-              : HTMLInputElement.prototype;
-            const descriptor = Object.getOwnPropertyDescriptor(proto, 'value');
-            if (descriptor && descriptor.set) descriptor.set.call(this, '');
-            else this.value = '';
-          }
-          this.dispatchEvent(new Event('input', { bubbles: true }));
-        }`,
-        returnByValue: true,
-      });
+    if (throwIfAborted(deps.signal)) {
+      return { code: "cancelled", message: "fill aborted" };
+    }
+    try {
+      await nodeCdp.send(target.tabId, "DOM.focus", { backendNodeId: node.backendNodeId });
+    } catch (error) {
+      // Chrome rejects DOM.focus for disabled controls, including inherited
+      // fieldset state. Classify the live target before treating this as a
+      // browser failure; the normal path needs no extra round trip.
+      const editable = await nodeCdp.send<FillScriptReply<boolean>>(
+        target.tabId,
+        "Runtime.callFunctionOn",
+        { objectId, functionDeclaration: FILL_EDITABLE_FUNCTION, returnByValue: true },
+      );
+      if (throwIfAborted(deps.signal)) {
+        return { code: "cancelled", message: "fill aborted" };
+      }
+      if (!editable.exceptionDetails && editable.result?.value === false) {
+        return fillError(
+          "target_not_fillable",
+          "fill target is not editable or its input type is unsupported",
+        );
+      }
+      throw error;
     }
     if (throwIfAborted(deps.signal)) {
       return { code: "cancelled", message: "fill aborted" };
     }
+    // Check editability before clearing. Keep the expected result tied to
+    // this object, including the existing value on the append path.
+    const prepared = await nodeCdp.send<FillScriptReply<FillPreparation>>(
+      target.tabId,
+      "Runtime.callFunctionOn",
+      {
+        objectId,
+        functionDeclaration: `function(value, clearBefore) {
+          const tag = this.tagName.toLowerCase();
+          const native = tag === 'input' || tag === 'textarea';
+          if (!(${FILL_EDITABLE_FUNCTION}).call(this)) return { reason: 'target_not_fillable', error: 'fill target is not editable or its input type is unsupported' };
+          if (this.getRootNode().activeElement !== this) return { reason: 'fill_focus_lost', error: 'fill target does not have focus' };
+          const before = clearBefore ? '' : (${FILL_VALUE_FUNCTION}).call(this);
+          let expected = before + value;
+          if (native) {
+            // Use the browser's own value sanitization (e.g. textarea
+            // line endings) without changing the live control.
+            const normalizer = this.ownerDocument.createElement(tag);
+            if (tag === 'input') {
+              normalizer.type = this.type;
+              normalizer.multiple = this.multiple;
+            }
+            // insertText treats line breaks in a single-line input as spaces.
+            if (tag === 'input') expected = expected.replace(/\\r\\n|\\r|\\n/g, ' ');
+            normalizer.value = expected;
+            if (expected !== '' && normalizer.value === '' && this.type === 'number') {
+              return { reason: 'fill_value_invalid', error: 'fill value is not valid for a number input' };
+            }
+            expected = normalizer.value;
+            if (this.type !== 'number' && this.maxLength >= 0 && expected.length > this.maxLength) {
+              return { reason: 'fill_value_invalid', error: 'fill value exceeds the target maxlength' };
+            }
+          } else {
+            expected = expected.replace(/\\r\\n?/g, '\\n');
+          }
+          if (clearBefore) {
+            if (native) {
+              const proto = tag === 'textarea' ? HTMLTextAreaElement.prototype : HTMLInputElement.prototype;
+              Object.getOwnPropertyDescriptor(proto, 'value').set.call(this, '');
+            } else {
+              this.textContent = '';
+            }
+            this.dispatchEvent(new Event('input', { bubbles: true }));
+          }
+          return { before, expected };
+        }`,
+        arguments: [{ value: params.value }, { value: clearBefore }],
+        returnByValue: true,
+      },
+    );
+    if (throwIfAborted(deps.signal)) {
+      return { code: "cancelled", message: "fill aborted" };
+    }
+    if (prepared.exceptionDetails) {
+      return fillError("fill_failed", "fill preparation script failed");
+    }
+    const preparation = prepared.result?.value;
+    if (preparation && "error" in preparation) {
+      return fillError(preparation.reason, preparation.error);
+    }
+    if (typeof preparation?.before !== "string" || typeof preparation?.expected !== "string") {
+      return fillError("fill_failed", "fill preparation returned an unexpected result");
+    }
+    // A separate call runs after the clearing event's microtasks drain.
+    // DOM focus works in background tabs. Use document.hasFocus() only to
+    // detect deferred focus events, never to reject background input.
+    const checkReady = async (): Promise<FillReadiness | RpcError> => {
+      const reply = await nodeCdp.send<FillScriptReply<FillReadiness>>(
+        target.tabId,
+        "Runtime.callFunctionOn",
+        {
+          objectId,
+          functionDeclaration: `function(before) {
+            if (!(${FILL_EDITABLE_FUNCTION}).call(this) ||
+                (${FILL_VALUE_FUNCTION}).call(this) !== before) return 'fill_target_changed';
+            if (this.getRootNode().activeElement !== this) return 'fill_focus_lost';
+            return this.ownerDocument.hasFocus() ? 'ready' : 'background';
+          }`,
+          arguments: [{ value: preparation.before }],
+          returnByValue: true,
+        },
+      );
+      const state = reply.result?.value;
+      if (
+        reply.exceptionDetails ||
+        (state !== "ready" &&
+          state !== "background" &&
+          state !== "fill_target_changed" &&
+          state !== "fill_focus_lost")
+      ) {
+        return fillError(
+          "fill_failed",
+          "fill readiness script failed or returned an unexpected result",
+        );
+      }
+      return state;
+    };
+    let ready = await checkReady();
+    if (throwIfAborted(deps.signal)) {
+      return { code: "cancelled", message: "fill aborted" };
+    }
+    // Restore focus once only if clearing left this same target editable
+    // and unchanged. Recheck after focus handlers have run.
+    if (clearBefore && ready === "fill_focus_lost") {
+      await nodeCdp.send(target.tabId, "DOM.focus", { backendNodeId: node.backendNodeId });
+      if (throwIfAborted(deps.signal)) {
+        return { code: "cancelled", message: "fill aborted" };
+      }
+      ready = await checkReady();
+    }
+    if (throwIfAborted(deps.signal)) {
+      return { code: "cancelled", message: "fill aborted" };
+    }
+    if (typeof ready !== "string") return ready;
+    if (ready !== "ready" && ready !== "background") {
+      return fillError(ready, "fill target changed or lost focus before typing");
+    }
+    if (params.value !== "" && (!clearBefore || ready === "background")) {
+      // Native editing commands also support number/email inputs, whose
+      // selection APIs cannot set a caret, and multiline contenteditables.
+      // Also do this for background replacement: CDP input focuses the
+      // renderer, delivering deferred focus events before it inserts text.
+      // Use a command-only event so this does not invoke an End shortcut.
+      try {
+        await deps.cdp.send(target.tabId, "Input.dispatchKeyEvent", {
+          type: "rawKeyDown",
+          commands: ["moveToEndOfDocument"],
+        });
+      } finally {
+        await deps.cdp.send(target.tabId, "Input.dispatchKeyEvent", { type: "keyUp" });
+      }
+      if (throwIfAborted(deps.signal)) {
+        return { code: "cancelled", message: "fill aborted" };
+      }
+      // Focus and key handlers can change the target or move focus too.
+      ready = await checkReady();
+      if (throwIfAborted(deps.signal)) {
+        return { code: "cancelled", message: "fill aborted" };
+      }
+      if (typeof ready !== "string") return ready;
+      if (ready !== "ready" && ready !== "background") {
+        return fillError(ready, "fill target changed or lost focus while positioning the caret");
+      }
+    }
     // CDP `Input.insertText` handles IME / multi-byte input out of the
     // box, much more reliably than per-key `dispatchKeyEvent`.
-    await deps.cdp.send(target.tabId, "Input.insertText", { text: params.value });
+    if (params.value !== "") {
+      await deps.cdp.send(target.tabId, "Input.insertText", { text: params.value });
+    }
     if (throwIfAborted(deps.signal)) {
       return { code: "cancelled", message: "fill aborted" };
     }
-    // Fire `input` + `change` so React / Vue controlled inputs commit.
-    await nodeCdp.send(target.tabId, "Runtime.callFunctionOn", {
+    // Keep the existing notifications, then read in a separate call so
+    // nested microtasks queued by the page cannot race the verification.
+    const notified = await nodeCdp.send<FillScriptReply<unknown>>(
+      target.tabId,
+      "Runtime.callFunctionOn",
+      {
+        objectId,
+        functionDeclaration: `function() {
+          this.dispatchEvent(new Event('input', { bubbles: true }));
+          this.dispatchEvent(new Event('change', { bubbles: true }));
+        }`,
+        returnByValue: true,
+      },
+    );
+    if (throwIfAborted(deps.signal)) {
+      return { code: "cancelled", message: "fill aborted" };
+    }
+    if (notified.exceptionDetails) {
+      return fillError("fill_failed", "fill notification script failed");
+    }
+    const verified = await nodeCdp.send<
+      FillScriptReply<{ connected: boolean; matches: boolean; valueLength: number }>
+    >(target.tabId, "Runtime.callFunctionOn", {
       objectId,
-      functionDeclaration: `function() {
-        this.dispatchEvent(new Event('input', { bubbles: true }));
-        this.dispatchEvent(new Event('change', { bubbles: true }));
-      }`,
+      functionDeclaration: `function(expected) {
+          const value = (${FILL_VALUE_FUNCTION}).call(this);
+          return { connected: this.isConnected, matches: value === expected, valueLength: value.length };
+        }`,
+      arguments: [{ value: preparation.expected }],
       returnByValue: true,
     });
+    if (throwIfAborted(deps.signal)) {
+      return { code: "cancelled", message: "fill aborted" };
+    }
+    const verification = verified.result?.value;
+    if (
+      verified.exceptionDetails ||
+      typeof verification?.connected !== "boolean" ||
+      typeof verification?.matches !== "boolean" ||
+      typeof verification?.valueLength !== "number"
+    ) {
+      return fillError(
+        "fill_failed",
+        "fill verification script failed or returned an unexpected result",
+      );
+    }
+    if (!verification.connected) {
+      return fillError("fill_target_changed", "fill target was removed or replaced during input");
+    }
+    if (!verification.matches) {
+      return fillError(
+        "fill_value_mismatch",
+        "fill could not verify the expected value; observe the page before deciding whether to retry",
+      );
+    }
+    return attachDialogs(deps.cdp, target.tabId, dialogCursor, {
+      tab_id: target.tabId,
+      used_ref: node.usedRef,
+      used_selector: node.usedSelector,
+      value_length: verification.valueLength,
+    });
   } catch (err) {
-    return {
-      code: "cdp_failed",
-      message: err instanceof Error ? err.message : String(err),
-    };
+    return fillError("fill_failed", err instanceof Error ? err.message : String(err));
+  } finally {
+    await nodeCdp.send(target.tabId, "Runtime.releaseObject", { objectId }).catch(() => undefined);
   }
-
-  return attachDialogs(deps.cdp, target.tabId, dialogCursor, {
-    tab_id: target.tabId,
-    used_ref: node.usedRef,
-    used_selector: node.usedSelector,
-    value_length: params.value.length,
-  });
 }
 
 // ---------------------------------------------------------------------------
diff --git a/apps/extension/src/transport/types.ts b/apps/extension/src/transport/types.ts
index fc9968a..f604993 100644
--- a/apps/extension/src/transport/types.ts
+++ b/apps/extension/src/transport/types.ts
@@ -26,6 +26,11 @@ export type RpcErrorReason =
   | "ref_not_found"
   | "selector_not_found"
   | "target_not_fillable"
+  | "fill_value_invalid"
+  | "fill_target_changed"
+  | "fill_focus_lost"
+  | "fill_value_mismatch"
+  | "fill_failed"
   | "target_not_select"
   | "option_not_found"
   | "single_select_value_count"
diff --git a/crates/bsk-cli/skill/SKILL.md b/crates/bsk-cli/skill/SKILL.md
index 357625c..f27ab2f 100644
--- a/crates/bsk-cli/skill/SKILL.md
+++ b/crates/bsk-cli/skill/SKILL.md
@@ -172,6 +172,10 @@ intended. Read `bsk upload --help` and `bsk download --help` for all flags and e
 - Stale ref: observe again and retry the intended action once.
 - Unknown tab or session: list current tabs/sessions; never guess identifiers.
 - Timeout: inspect current page state before deciding whether one longer purposeful wait is useful.
+- Fill result unconfirmed (`fill_value_mismatch`): observe the field first; the page may have
+  formatted the value. Continue if the visible result satisfies the user's intent. Otherwise correct
+  the remaining difference; do not blindly repeat fill or immediately request human help. For other
+  fill errors, follow the returned hint and inspect current state before retrying.
 - Unsupported command: continue with available capabilities; suggest updating only when the missing
   command is necessary.
 - Unrecoverable failure: report the blocker and stop the session in a finally-style path.
diff --git a/crates/bsk-cli/src/cli/render_error.rs b/crates/bsk-cli/src/cli/render_error.rs
index 01f80dd..ef9312f 100644
--- a/crates/bsk-cli/src/cli/render_error.rs
+++ b/crates/bsk-cli/src/cli/render_error.rs
@@ -43,6 +43,11 @@ pub mod reason {
     pub const REF_NOT_FOUND: &str = "ref_not_found";
     pub const SELECTOR_NOT_FOUND: &str = "selector_not_found";
     pub const TARGET_NOT_FILLABLE: &str = "target_not_fillable";
+    pub const FILL_VALUE_INVALID: &str = "fill_value_invalid";
+    pub const FILL_TARGET_CHANGED: &str = "fill_target_changed";
+    pub const FILL_FOCUS_LOST: &str = "fill_focus_lost";
+    pub const FILL_VALUE_MISMATCH: &str = "fill_value_mismatch";
+    pub const FILL_FAILED: &str = "fill_failed";
     pub const TARGET_NOT_SELECT: &str = "target_not_select";
     pub const OPTION_NOT_FOUND: &str = "option_not_found";
     pub const SINGLE_SELECT_VALUE_COUNT: &str = "single_select_value_count";
@@ -247,7 +252,42 @@ pub fn info_for_error(code: ErrorCode, data: Option<&serde_json::Value>) -> Rend
         (ErrorCode::InvalidParams, reason::TARGET_NOT_FILLABLE) => RenderInfo {
             summary: "target element is not fillable",
             hint: Some(
-                "choose an input, textarea, or contenteditable element from the latest snapshot",
+                "observe the page and choose an enabled, editable text input, textarea, or contenteditable; use the appropriate interaction for other control types",
+            ),
+            exit_code: base.exit_code,
+        },
+        (ErrorCode::InvalidParams, reason::FILL_VALUE_INVALID) => RenderInfo {
+            summary: "the requested text does not fit the field constraints",
+            hint: Some(
+                "check the field's input type and maxlength; use a compatible value without silently truncating or changing the user's intended data",
+            ),
+            exit_code: base.exit_code,
+        },
+        (ErrorCode::CdpFailed, reason::FILL_TARGET_CHANGED) => RenderInfo {
+            summary: "the fill target changed during the action",
+            hint: Some(
+                "observe the current page and field value; if the intended result is missing, use a fresh editable target before retrying",
+            ),
+            exit_code: base.exit_code,
+        },
+        (ErrorCode::CdpFailed, reason::FILL_FOCUS_LOST) => RenderInfo {
+            summary: "the page moved focus away from the fill target",
+            hint: Some(
+                "observe the page for a dialog or rerender and resolve it before retrying; fill manages field focus and does not require bringing the browser to the foreground",
+            ),
+            exit_code: base.exit_code,
+        },
+        (ErrorCode::CdpFailed, reason::FILL_VALUE_MISMATCH) => RenderInfo {
+            summary: "the fill result could not be confirmed",
+            hint: Some(
+                "observe the field before retrying; the page may have formatted the value. Continue if the visible result satisfies the user's intent; otherwise correct the remaining difference. Do not blindly repeat fill or immediately request human help",
+            ),
+            exit_code: base.exit_code,
+        },
+        (ErrorCode::CdpFailed, reason::FILL_FAILED) => RenderInfo {
+            summary: "fill encountered a browser or page-script error",
+            hint: Some(
+                "observe the page before retrying because the field may already have changed; retry only if the intended result is missing and the target is still available",
             ),
             exit_code: base.exit_code,
         },
@@ -442,6 +482,56 @@ mod tests {
         ErrorCode::NoBrowserConnected,
     ];
 
+    #[test]
+    fn fill_reasons_provide_recovery_without_changing_exit_codes() {
+        for (code, reason, hint_fragment) in [
+            (
+                ErrorCode::InvalidParams,
+                reason::TARGET_NOT_FILLABLE,
+                "enabled, editable",
+            ),
+            (
+                ErrorCode::InvalidParams,
+                reason::FILL_VALUE_INVALID,
+                "maxlength",
+            ),
+            (
+                ErrorCode::CdpFailed,
+                reason::FILL_TARGET_CHANGED,
+                "fresh editable target",
+            ),
+            (
+                ErrorCode::CdpFailed,
+                reason::FILL_FOCUS_LOST,
+                "does not require bringing the browser",
+            ),
+            (
+                ErrorCode::CdpFailed,
+                reason::FILL_VALUE_MISMATCH,
+                "Continue if the visible result satisfies",
+            ),
+            (
+                ErrorCode::CdpFailed,
+                reason::FILL_FAILED,
+                "may already have changed",
+            ),
+        ] {
+            let data = serde_json::json!({ "reason": reason });
+            let info = info_for_error(code, Some(&data));
+            assert!(info.hint.unwrap().contains(hint_fragment), "{reason}");
+            assert_eq!(info.exit_code, info_for(code).exit_code);
+        }
+        let mismatch = serde_json::json!({ "reason": reason::FILL_VALUE_MISMATCH });
+        let info = info_for_error(ErrorCode::CdpFailed, Some(&mismatch));
+        assert_eq!(info.summary, "the fill result could not be confirmed");
+        assert!(info.hint.unwrap().contains("Do not blindly repeat fill"));
+        let unknown = serde_json::json!({ "reason": "future_fill_reason" });
+        assert_eq!(
+            info_for_error(ErrorCode::CdpFailed, Some(&unknown)),
+            info_for(ErrorCode::CdpFailed)
+        );
+    }
+
     #[test]
     fn element_not_visible_overrides_permission_denied_copy() {
         let data = serde_json::json!({ "reason": reason::ELEMENT_NOT_VISIBLE });
diff --git a/packages/dsh-plugin-browserskill/skill/SKILL.md b/packages/dsh-plugin-browserskill/skill/SKILL.md
index a2d9c4e..464a24e 100644
--- a/packages/dsh-plugin-browserskill/skill/SKILL.md
+++ b/packages/dsh-plugin-browserskill/skill/SKILL.md
@@ -97,6 +97,10 @@ Continue from returned sequence cursors instead of rereading the same buffer.
 - Unknown tab: list tabs instead of guessing.
 - Unknown session: list owned sessions or start one; never try foreign ids.
 - Timeout: inspect current state before deciding whether one longer purposeful wait is useful.
+- Fill result unconfirmed: observe the field first; the page may have formatted the value. Continue
+  if the visible result satisfies the user's intent. Otherwise correct the remaining difference;
+  do not blindly repeat fill or immediately request human help. For other fill errors, follow the
+  returned hint and inspect current state before retrying.
 - Unrecoverable failure: report the blocker and stop the owned session.
 
 Arbitrary page-script evaluation and interaction recording are intentionally unsupported. Do not
diff --git a/packages/dsh-plugin-browserskill/src/tools.ts b/packages/dsh-plugin-browserskill/src/tools.ts
index 9bdbabe..db8738f 100644
--- a/packages/dsh-plugin-browserskill/src/tools.ts
+++ b/packages/dsh-plugin-browserskill/src/tools.ts
@@ -636,7 +636,9 @@ function defineBrowserOperations(deps: ToolDeps, register: DefinitionRegistrar):
         session: SESSION_PARAM,
         noClear: {
           type: "boolean",
-          description: "Skip the default wipe-the-field-first pass (append instead).",
+          description:
+            "Append to the end of the existing value instead of clearing it. " +
+            "The tool moves the caret automatically; no prior click or selection is needed.",
         },
       },
       output: {
diff --git a/packages/dsh-plugin-browserskill/tests/runner.test.ts b/packages/dsh-plugin-browserskill/tests/runner.test.ts
index 37b2de1..ad6d81a 100644
--- a/packages/dsh-plugin-browserskill/tests/runner.test.ts
+++ b/packages/dsh-plugin-browserskill/tests/runner.test.ts
@@ -124,6 +124,28 @@ describe("parseBskJson", () => {
     expect(() => parseBskJson({ ...base, code: 1, stderr: "boom" }, "x")).toThrow(/boom/);
   });
 
+  it("surfaces fill recovery guidance to the model without retrying", async () => {
+    const hint =
+      "observe the field before retrying; the page may have formatted the value. Continue if the visible result satisfies the user's intent";
+    const reply = {
+      ...base,
+      code: 3,
+      stdout: JSON.stringify({
+        code: "cdp_failed",
+        message: "fill could not verify the expected value",
+        data: { reason: "fill_value_mismatch" },
+        hint,
+      }),
+    };
+    let calls = 0;
+    const result = await runWithSessionBusyRetry(async () => {
+      calls++;
+      return reply;
+    });
+    expect(calls).toBe(1);
+    expect(() => parseBskJson(result, "fill")).toThrow(hint);
+  });
+
   it("reports killed-by-interrupt children (null exit code) as interrupted", () => {
     expect(() => parseBskJson({ ...base, code: null }, "navigate")).toThrow(/interrupted/);
   });
diff --git a/skill/SKILL.md b/skill/SKILL.md
index 357625c..f27ab2f 100644
--- a/skill/SKILL.md
+++ b/skill/SKILL.md
@@ -172,6 +172,10 @@ intended. Read `bsk upload --help` and `bsk download --help` for all flags and e
 - Stale ref: observe again and retry the intended action once.
 - Unknown tab or session: list current tabs/sessions; never guess identifiers.
 - Timeout: inspect current page state before deciding whether one longer purposeful wait is useful.
+- Fill result unconfirmed (`fill_value_mismatch`): observe the field first; the page may have
+  formatted the value. Continue if the visible result satisfies the user's intent. Otherwise correct
+  the remaining difference; do not blindly repeat fill or immediately request human help. For other
+  fill errors, follow the returned hint and inspect current state before retrying.
 - Unsupported command: continue with available capabilities; suggest updating only when the missing
   command is necessary.
 - Unrecoverable failure: report the blocker and stop the session in a finally-style path.