diff --git a/packages/shared/src/types/issue.ts b/packages/shared/src/types/issue.ts
index 46ef3010..20d14342 100644
--- a/packages/shared/src/types/issue.ts
+++ b/packages/shared/src/types/issue.ts
@@ -722,6 +722,7 @@ export interface AskUserQuestionsPayload {
 export interface AskUserQuestionsAnswer {
   questionId: string;
   optionIds: string[];
+  otherText?: string | null;
 }
 
 export interface AskUserQuestionsResult {
diff --git a/packages/shared/src/validators/issue.ts b/packages/shared/src/validators/issue.ts
index cd532dc9..2b8740f5 100644
--- a/packages/shared/src/validators/issue.ts
+++ b/packages/shared/src/validators/issue.ts
@@ -666,6 +666,7 @@ export const askUserQuestionsPayloadSchema = z.object({
 export const askUserQuestionsAnswerSchema = z.object({
   questionId: z.string().trim().min(1).max(120),
   optionIds: z.array(z.string().trim().min(1).max(120)).max(20),
+  otherText: multilineTextSchema.pipe(z.string().trim().max(4000)).nullable().optional(),
 });
 
 export const askUserQuestionsResultSchema = z.object({
diff --git a/server/src/__tests__/issue-thread-interactions-service.test.ts b/server/src/__tests__/issue-thread-interactions-service.test.ts
index 286bf590..f381768b 100644
--- a/server/src/__tests__/issue-thread-interactions-service.test.ts
+++ b/server/src/__tests__/issue-thread-interactions-service.test.ts
@@ -453,8 +453,12 @@ describeEmbeddedPostgres("issueThreadInteractionService", () => {
       companyId,
     }, created.id, {
       answers: [
-        { questionId: "scope", optionIds: ["phase-1"] },
-        { questionId: "extras", optionIds: ["docs", "tests", "docs"] },
+        { questionId: "scope", optionIds: [], otherText: "Custom Phase 1" },
+        {
+          questionId: "extras",
+          optionIds: ["docs", "tests", "docs"],
+          otherText: "  Pair with release notes  ",
+        },
       ],
       summaryMarkdown: "Ship Phase 1 with tests and docs.",
     }, {
@@ -465,8 +469,8 @@ describeEmbeddedPostgres("issueThreadInteractionService", () => {
     expect(answered.result).toEqual({
       version: 1,
       answers: [
-        { questionId: "scope", optionIds: ["phase-1"] },
-        { questionId: "extras", optionIds: ["docs", "tests"] },
+        { questionId: "scope", optionIds: [], otherText: "Custom Phase 1" },
+        { questionId: "extras", optionIds: ["docs", "tests"], otherText: "Pair with release notes" },
       ],
       summaryMarkdown: "Ship Phase 1 with tests and docs.",
     });
diff --git a/server/src/services/issue-thread-interactions.ts b/server/src/services/issue-thread-interactions.ts
index 533d3a2e..f27ec37e 100644
--- a/server/src/services/issue-thread-interactions.ts
+++ b/server/src/services/issue-thread-interactions.ts
@@ -272,15 +272,20 @@ function normalizeQuestionAnswers(args: {
       throw unprocessable(`Question ${answer.questionId} only allows one answer`);
     }
 
+    const otherText = answer.otherText?.trim() ?? "";
     answerByQuestionId.set(answer.questionId, {
       questionId: answer.questionId,
       optionIds: uniqueOptionIds,
+      ...(otherText ? { otherText } : {}),
     });
   }
 
   for (const question of args.questions) {
     const answer = answerByQuestionId.get(question.id);
-    if (question.required && (!answer || answer.optionIds.length === 0)) {
+    if (
+      question.required
+      && (!answer || (answer.optionIds.length === 0 && !answer.otherText))
+    ) {
       throw unprocessable(`Question ${question.id} requires an answer`);
     }
   }
diff --git a/ui/src/components/IssueChatThread.test.tsx b/ui/src/components/IssueChatThread.test.tsx
index 3ad29546..4faf0aa7 100644
--- a/ui/src/components/IssueChatThread.test.tsx
+++ b/ui/src/components/IssueChatThread.test.tsx
@@ -1627,6 +1627,70 @@ describe("IssueChatThread", () => {
     });
   });
 
+  it("submits Other text for pending question interactions", async () => {
+    const root = createRoot(container);
+    const onSubmitInteractionAnswers = vi.fn(async () => undefined);
+
+    await act(async () => {
+      root.render(
+        <MemoryRouter>
+          <IssueChatThread
+            comments={[]}
+            interactions={[createQuestionInteraction()]}
+            linkedRuns={[]}
+            timelineEvents={[]}
+            liveRuns={[]}
+            onAdd={async () => {}}
+            onSubmitInteractionAnswers={onSubmitInteractionAnswers}
+            showComposer={false}
+            enableLiveTranscriptPolling={false}
+          />
+        </MemoryRouter>,
+      );
+    });
+
+    const otherButton = Array.from(container.querySelectorAll("button")).find((button) =>
+      button.textContent?.includes("Other"),
+    );
+    expect(otherButton).toBeTruthy();
+
+    await act(async () => {
+      otherButton?.dispatchEvent(new MouseEvent("click", { bubbles: true }));
+    });
+
+    const textarea = container.querySelector("textarea") as HTMLTextAreaElement | null;
+    expect(textarea).toBeTruthy();
+
+    await act(async () => {
+      const valueSetter = Object.getOwnPropertyDescriptor(
+        HTMLTextAreaElement.prototype,
+        "value",
+      )?.set;
+      valueSetter?.call(textarea, "Phase 1 plus docs");
+      textarea!.dispatchEvent(new Event("input", { bubbles: true }));
+    });
+
+    const submitButton = Array.from(container.querySelectorAll("button")).find((button) =>
+      button.textContent?.includes("Submit answers"),
+    );
+
+    await act(async () => {
+      submitButton?.dispatchEvent(new MouseEvent("click", { bubbles: true }));
+    });
+
+    expect(onSubmitInteractionAnswers).toHaveBeenCalledWith(
+      expect.objectContaining({
+        id: "interaction-question-1",
+        kind: "ask_user_questions",
+      }),
+      [{ questionId: "scope", optionIds: [], otherText: "Phase 1 plus docs" }],
+    );
+
+    act(() => {
+      root.unmount();
+    });
+  });
+
   it("invokes the cancel callback for pending question interactions", async () => {
     const root = createRoot(container);
     const onCancelInteraction = vi.fn(async () => undefined);
diff --git a/ui/src/components/IssueThreadInteractionCard.test.tsx b/ui/src/components/IssueThreadInteractionCard.test.tsx
index b289c72a..eeda1cf6 100644
--- a/ui/src/components/IssueThreadInteractionCard.test.tsx
+++ b/ui/src/components/IssueThreadInteractionCard.test.tsx
@@ -74,7 +74,7 @@ describe("IssueThreadInteractionCard", () => {
     );
 
     const radios = [...host.querySelectorAll('[role="radio"]')];
-    expect(radios).toHaveLength(2);
+    expect(radios).toHaveLength(3);
     expect(radios[0]?.getAttribute("aria-checked")).toBe("false");
 
     act(() => {
@@ -88,7 +88,65 @@ describe("IssueThreadInteractionCard", () => {
     expect(multiGroup?.getAttribute("aria-labelledby")).toBe(
       "interaction-questions-default-post-submit-summary-prompt",
     );
-    expect(host.querySelectorAll('[role="checkbox"]')).toHaveLength(3);
+    expect(host.querySelectorAll('[role="checkbox"]')).toHaveLength(4);
+  });
+
+  it("submits written Other answers for pending questions", async () => {
+    const onSubmitInteractionAnswers = vi.fn(async () => undefined);
+    const host = renderCard({
+      interaction: pendingAskUserQuestionsInteraction,
+      onSubmitInteractionAnswers,
+    });
+
+    const otherButtons = Array.from(host.querySelectorAll("button")).filter((button) =>
+      button.textContent?.includes("Other"),
+    );
+    expect(otherButtons.length).toBeGreaterThan(0);
+
+    await act(async () => {
+      otherButtons[0]?.dispatchEvent(new MouseEvent("click", { bubbles: true }));
+    });
+
+    const textarea = host.querySelector("textarea") as HTMLTextAreaElement | null;
+    expect(textarea).toBeTruthy();
+
+    await act(async () => {
+      const valueSetter = Object.getOwnPropertyDescriptor(
+        HTMLTextAreaElement.prototype,
+        "value",
+      )?.set;
+      valueSetter?.call(textarea, "Keep only the root item open");
+      textarea!.dispatchEvent(new Event("input", { bubbles: true }));
+    });
+
+    const summaryCheckbox = Array.from(host.querySelectorAll('[role="checkbox"]')).find((button) =>
+      button.textContent?.includes("Inline answer pills"),
+    );
+    await act(async () => {
+      summaryCheckbox?.dispatchEvent(new MouseEvent("click", { bubbles: true }));
+    });
+
+    const submitButton = Array.from(host.querySelectorAll("button")).find((button) =>
+      button.textContent?.includes("Send answers"),
+    );
+    await act(async () => {
+      submitButton?.dispatchEvent(new MouseEvent("click", { bubbles: true }));
+    });
+
+    expect(onSubmitInteractionAnswers).toHaveBeenCalledWith(
+      expect.objectContaining({ kind: "ask_user_questions" }),
+      [
+        {
+          questionId: "collapse-depth",
+          optionIds: [],
+          otherText: "Keep only the root item open",
+        },
+        {
+          questionId: "post-submit-summary",
+          optionIds: ["answers-inline"],
+        },
+      ],
+    );
   });
 
   it("only shows question cancellation when a cancel handler is wired", () => {
diff --git a/ui/src/components/IssueThreadInteractionCard.tsx b/ui/src/components/IssueThreadInteractionCard.tsx
index a05f0dc2..ca5fb09f 100644
--- a/ui/src/components/IssueThreadInteractionCard.tsx
+++ b/ui/src/components/IssueThreadInteractionCard.tsx
@@ -26,6 +26,8 @@ import { PriorityIcon } from "./PriorityIcon";
 import { Textarea } from "./ui/textarea";
 import { Tooltip, TooltipContent, TooltipTrigger } from "./ui/tooltip";
 
+const OTHER_ANSWER_ID = "__paperclip_other__";
+
 interface IssueThreadInteractionCardProps {
   interaction: IssueThreadInteraction;
   agentMap?: Map<string, Agent>;
@@ -662,6 +664,20 @@ function AskUserQuestionsCard({
       ]),
     ),
   );
+  const [draftOtherAnswers, setDraftOtherAnswers] = useState<Record<string, string>>(() =>
+    Object.fromEntries(
+      (interaction.result?.answers ?? [])
+        .filter((answer) => answer.otherText)
+        .map((answer) => [answer.questionId, answer.otherText ?? ""]),
+    ),
+  );
+  const [otherActiveQuestions, setOtherActiveQuestions] = useState<Record<string, boolean>>(() =>
+    Object.fromEntries(
+      (interaction.result?.answers ?? [])
+        .filter((answer) => answer.otherText)
+        .map((answer) => [answer.questionId, true]),
+    ),
+  );
   const [working, setWorking] = useState(false);
   const [cancelling, setCancelling] = useState(false);
 
@@ -674,15 +690,45 @@ function AskUserQuestionsCard({
         ]),
       ),
     );
+    setDraftOtherAnswers(
+      Object.fromEntries(
+        (interaction.result?.answers ?? [])
+          .filter((answer) => answer.otherText)
+          .map((answer) => [answer.questionId, answer.otherText ?? ""]),
+      ),
+    );
+    setOtherActiveQuestions(
+      Object.fromEntries(
+        (interaction.result?.answers ?? [])
+          .filter((answer) => answer.otherText)
+          .map((answer) => [answer.questionId, true]),
+      ),
+    );
   }, [interaction.result?.answers]);
 
   const questions = interaction.payload.questions;
   const requiredQuestions = questions.filter((question) => question.required);
   const canSubmit = requiredQuestions.every(
-    (question) => (draftAnswers[question.id] ?? []).length > 0,
+    (question) =>
+      (draftAnswers[question.id] ?? []).length > 0
+      || (
+        otherActiveQuestions[question.id] === true
+        && (draftOtherAnswers[question.id]?.trim().length ?? 0) > 0
+      ),
   );
 
   function toggleOption(questionId: string, optionId: string, selectionMode: "single" | "multi") {
+    if (optionId === OTHER_ANSWER_ID) {
+      setOtherActiveQuestions((current) => ({
+        ...current,
+        [questionId]: !current[questionId],
+      }));
+      if (selectionMode === "single") {
+        setDraftAnswers((current) => ({ ...current, [questionId]: [] }));
+      }
+      return;
+    }
+
     setDraftAnswers((current) => {
       const existing = current[questionId] ?? [];
       if (selectionMode === "single") {
@@ -693,6 +739,9 @@ function AskUserQuestionsCard({
         : [...existing, optionId];
       return { ...current, [questionId]: next };
     });
+    if (selectionMode === "single") {
+      setOtherActiveQuestions((current) => ({ ...current, [questionId]: false }));
+    }
   }
 
   async function handleSubmit() {
@@ -701,10 +750,16 @@ function AskUserQuestionsCard({
     try {
       await onSubmitInteractionAnswers(
         interaction,
-        questions.map((question) => ({
-          questionId: question.id,
-          optionIds: draftAnswers[question.id] ?? [],
-        })),
+        questions.map((question) => {
+          const otherText = otherActiveQuestions[question.id] === true
+            ? draftOtherAnswers[question.id]?.trim() ?? ""
+            : "";
+          return {
+            questionId: question.id,
+            optionIds: draftAnswers[question.id] ?? [],
+            ...(otherText ? { otherText } : {}),
+          };
+        }),
       );
     } finally {
       setWorking(false);
@@ -783,6 +838,28 @@ function AskUserQuestionsCard({
                       toggleOption(question.id, option.id, question.selectionMode)}
                   />
                 ))}
+                <QuestionOptionButton
+                  id={`${interaction.id}-${question.id}-other`}
+                  label="Other"
+                  description="Use a written answer instead of the listed choices."
+                  selected={otherActiveQuestions[question.id] === true}
+                  selectionMode={question.selectionMode}
+                  onClick={() =>
+                    toggleOption(question.id, OTHER_ANSWER_ID, question.selectionMode)}
+                />
+                {otherActiveQuestions[question.id] ? (
+                  <Textarea
+                    aria-label={`Other answer for ${question.prompt}`}
+                    value={draftOtherAnswers[question.id] ?? ""}
+                    onChange={(event) =>
+                      setDraftOtherAnswers((current) => ({
+                        ...current,
+                        [question.id]: event.target.value,
+                      }))}
+                    placeholder="Type your answer"
+                    className="min-h-24 bg-background text-sm"
+                  />
+                ) : null}
               </div>
             </div>
           ))}
diff --git a/ui/src/lib/issue-thread-interactions.test.ts b/ui/src/lib/issue-thread-interactions.test.ts
index ec744b28..5022aa79 100644
--- a/ui/src/lib/issue-thread-interactions.test.ts
+++ b/ui/src/lib/issue-thread-interactions.test.ts
@@ -141,10 +141,11 @@ describe("issue thread interaction helpers", () => {
         {
           questionId: "question-1",
           optionIds: ["option-2", "option-1"],
+          otherText: "A written answer",
         },
       ],
     });
 
-    expect(labels).toEqual(["Option 2", "Option 1"]);
+    expect(labels).toEqual(["Option 2", "Option 1", "Other: A written answer"]);
   });
 });
diff --git a/ui/src/lib/issue-thread-interactions.ts b/ui/src/lib/issue-thread-interactions.ts
index 25333eff..19cd4bd1 100644
--- a/ui/src/lib/issue-thread-interactions.ts
+++ b/ui/src/lib/issue-thread-interactions.ts
@@ -132,12 +132,15 @@ export function getQuestionAnswerLabels(args: {
   answers: readonly AskUserQuestionsAnswer[];
 }) {
   const { question, answers } = args;
-  const selectedIds =
-    answers.find((answer) => answer.questionId === question.id)?.optionIds ?? [];
+  const answer = answers.find((candidate) => candidate.questionId === question.id);
+  const selectedIds = answer?.optionIds ?? [];
   const optionLabelById = new Map(
     question.options.map((option) => [option.id, option.label] as const),
   );
-  return selectedIds
+  const labels = selectedIds
     .map((optionId) => optionLabelById.get(optionId))
     .filter((label): label is string => typeof label === "string");
+  const otherText = answer?.otherText?.trim();
+  if (otherText) labels.push(`Other: ${otherText}`);
+  return labels;
 }