diff --git a/src/elicitation.ts b/src/elicitation.ts
index 57a14930..ded03a2f 100644
--- a/src/elicitation.ts
+++ b/src/elicitation.ts
@@ -168,9 +168,10 @@ const CUSTOM_ANSWER_META_KEY = "_askUserQuestionCustomAnswer";
  *
  * Each question is followed by its own optional free-text "custom answer" field
  * (`question_<n>_custom`), mirroring the CLI's per-question "Other" box: the
- * user can type their own answer instead of picking an option, scoped to that
- * specific question. Nothing is marked required, so the user can also just skip
- * — matching the built-in tool, which always offers Skip + a free-text box.
+ * user can type their own answer instead of (or, for a multi-select question,
+ * as well as) picking an option, scoped to that specific question. Nothing is
+ * marked required, so the user can also just skip — matching the built-in tool,
+ * which always offers Skip + a free-text box.
  */
 export function askUserQuestionsToCreateRequest(
   questions: AskUserQuestion[],
@@ -211,7 +212,9 @@ export function askUserQuestionsToCreateRequest(
     properties[questionCustomFieldKey(index)] = {
       type: "string",
       title: "Other",
-      description: "Type your own answer instead of choosing an option above (optional).",
+      description: question.multiSelect
+        ? "Type your own answer to add to your selection above (optional)."
+        : "Type your own answer instead of choosing an option above (optional).",
       _meta: {
         [CUSTOM_ANSWER_META_KEY]: {
           questionId: questionFieldKey(index),
@@ -241,17 +244,32 @@ export function askUserQuestionsToCreateRequest(
 export type AskUserQuestionOutcome =
   { action: "answered"; updatedInput: Record<string, unknown> } | { action: "cancel" };
 
+/**
+ * Serialize a multi-select answer the way the CLI's own AskUserQuestion UI
+ * does: comma-joined, with any item that itself contains the separator (or a
+ * double quote) JSON-quoted. The tool's `call()` splits the string back on the
+ * same rule, so a free-text answer like `Redis, not Memcached` stays one item
+ * instead of reading as two more picks.
+ */
+function joinMultiSelectAnswer(items: string[]): string {
+  return items
+    .map((item) => (item.includes(", ") || item.includes('"') ? JSON.stringify(item) : item))
+    .join(", ");
+}
+
 /**
  * Fold an ACP elicitation response into the AskUserQuestion tool's input.
  *
  * Selected labels are read back from the indexed form fields and written into
- * `answers` as a `{ [questionText]: label }` map (comma-joining multi-selects)
- * — the key shape the tool's own `call()` reads. A non-empty per-question
- * custom-answer field (`question_<n>_custom`) takes precedence over that
- * question's selection, since the user typed their own answer instead of
- * picking one. Decline yields empty answers (the model is told the user skipped
- * rather than the turn aborting); cancel — and any custom/future action we
- * don't understand — aborts the tool call.
+ * `answers` as a `{ [questionText]: label }` map — the key shape the tool's own
+ * `call()` reads — with multi-selects comma-joined in the CLI's own quoted form
+ * (see `joinMultiSelectAnswer`). A non-empty per-question custom-answer field
+ * (`question_<n>_custom`) replaces the selection of a single-select question,
+ * since the user typed their own answer instead of picking one, and joins the
+ * selection of a multi-select question, where the two fields are independent
+ * and filling both means both. Decline yields empty answers (the model is told
+ * the user skipped rather than the turn aborting); cancel — and any
+ * custom/future action we don't understand — aborts the tool call.
  */
 export function applyAskElicitationResponse(
   response: CreateElicitationResponse,
@@ -271,19 +289,28 @@ export function applyAskElicitationResponse(
   // stay in sync with what the built-in tool's call() expects to read back.
   const answers: AskUserQuestionOutput["answers"] = {};
   questions.forEach((question, index) => {
-    // A typed custom answer wins over the selection: the user chose to write
-    // their own answer for this question instead of picking an option.
     const custom = content[questionCustomFieldKey(index)];
-    if (typeof custom === "string" && custom.trim() !== "") {
-      answers[question.question] = custom.trim();
-      return;
-    }
+    const customText = typeof custom === "string" ? custom.trim() : "";
 
     const value = content[questionFieldKey(index)];
-    if (value === undefined || value === null) {
-      return;
-    }
-    const text = Array.isArray(value) ? value.join(", ") : String(value);
+    const picks: string[] =
+      value === undefined || value === null
+        ? []
+        : Array.isArray(value)
+          ? value.filter((item) => item !== undefined && item !== null && item !== "").map(String)
+          : [String(value)];
+
+    // A single-select question is answered by exactly one thing, so a typed
+    // custom answer replaces the pick: the user wrote their own answer instead
+    // of choosing an option. A multi-select is additive, and the form offers
+    // the selection and the custom box as independent fields — a user who
+    // fills both means both, so the typed answer joins the checked options.
+    const items =
+      customText === "" ? picks : question.multiSelect ? [...picks, customText] : [customText];
+
+    // A single-select normally holds one item; the plain join only matters if a
+    // client hands back an array for it, and then mirrors the old behavior.
+    const text = question.multiSelect ? joinMultiSelectAnswer(items) : items.join(", ");
     if (text === "") {
       return;
     }
diff --git a/src/tests/elicitation.test.ts b/src/tests/elicitation.test.ts
index f8e2b9ca..827d98d3 100644
--- a/src/tests/elicitation.test.ts
+++ b/src/tests/elicitation.test.ts
@@ -334,7 +334,7 @@ describe("applyAskElicitationResponse", () => {
     });
   });
 
-  it("folds a per-question custom answer into that question's answer", () => {
+  it("uses a multi-select question's custom answer alone when nothing is selected", () => {
     const response = {
       action: "accept",
       content: { question_0: "A", question_1_custom: "something else entirely" },
@@ -350,7 +350,7 @@ describe("applyAskElicitationResponse", () => {
     });
   });
 
-  it("prefers a question's custom answer over its selection", () => {
+  it("prefers a single-select question's custom answer over its selection", () => {
     const response = {
       action: "accept",
       content: { question_0: "A", question_0_custom: "  my own take  " },
@@ -366,6 +366,75 @@ describe("applyAskElicitationResponse", () => {
     });
   });
 
+  it("appends a multi-select question's custom answer to its selections", () => {
+    const response = {
+      action: "accept",
+      content: { question_1: ["X", "Y"], question_1_custom: "  Z  " },
+    } as CreateElicitationResponse;
+
+    expect(applyAskElicitationResponse(response, toolInput, questions)).toEqual({
+      action: "answered",
+      updatedInput: {
+        questions,
+        metadata: { source: "test" },
+        answers: { "Multi?": "X, Y, Z" },
+      },
+    });
+  });
+
+  it("quotes a multi-select custom answer that contains the separator, as the CLI does", () => {
+    const response = {
+      action: "accept",
+      content: { question_1: ["X"], question_1_custom: "Use Redis, not Memcached" },
+    } as CreateElicitationResponse;
+
+    expect(applyAskElicitationResponse(response, toolInput, questions)).toEqual({
+      action: "answered",
+      updatedInput: {
+        questions,
+        metadata: { source: "test" },
+        answers: { "Multi?": 'X, "Use Redis, not Memcached"' },
+      },
+    });
+  });
+
+  it("keeps the selection when the custom answer is blank", () => {
+    const response = {
+      action: "accept",
+      content: {
+        question_0: "A",
+        question_0_custom: "  ",
+        question_1: ["X"],
+        question_1_custom: " ",
+      },
+    } as CreateElicitationResponse;
+
+    expect(applyAskElicitationResponse(response, toolInput, questions)).toEqual({
+      action: "answered",
+      updatedInput: {
+        questions,
+        metadata: { source: "test" },
+        answers: { "Single?": "A", "Multi?": "X" },
+      },
+    });
+  });
+
+  it("uses the custom answer alone when the multi-select array is empty", () => {
+    const response = {
+      action: "accept",
+      content: { question_1: [], question_1_custom: "Z" },
+    } as CreateElicitationResponse;
+
+    expect(applyAskElicitationResponse(response, toolInput, questions)).toEqual({
+      action: "answered",
+      updatedInput: {
+        questions,
+        metadata: { source: "test" },
+        answers: { "Multi?": "Z" },
+      },
+    });
+  });
+
   it("ignores empty selections and blank custom answers", () => {
     const response = {
       action: "accept",