diff --git a/docs/contract.md b/docs/contract.md
index 0446c60..2733699 100644
--- a/docs/contract.md
+++ b/docs/contract.md
@@ -172,6 +172,8 @@ This document defines the stable external behavior. It does not explain internal
 - on single-select questions, saving free-form text clears selected options for that question
 - on multi-select questions, `values` and `labels` include both selected options and `customText` when both are present
 - on multi-select questions, selected options keep their original order and `customText` is appended last
+- submitting free-form text on a multi-select question stays on the same question tab and marks the custom row selected
+- on multi-select questions, toggling an empty custom row opens the free-form editor, while toggling a custom row with saved free-form text selects or deselects it without opening the editor or clearing the text
 - saving or clearing free-form text on a multi-select question does not clear other selected options
 - `note` stores a question-level note
 - `optionNotes` includes only notes for selected options
diff --git a/src/state/answers.ts b/src/state/answers.ts
index 46d683f..4a67bd3 100644
--- a/src/state/answers.ts
+++ b/src/state/answers.ts
@@ -17,6 +17,7 @@ export function emptyAnswer(): AskStateAnswer {
 export function cloneAnswer(answer: AskStateAnswer): AskStateAnswer {
 	return {
 		selected: answer.selected.map(cloneSelection),
+		customSelected: answer.customSelected,
 		customText: answer.customText,
 		note: answer.note,
 		optionNotes: answer.optionNotes ? { ...answer.optionNotes } : undefined,
@@ -87,13 +88,24 @@ export function saveCustomText(
 		next.selected = [];
 	}
 	if (!trimmed) {
+		next.customSelected = undefined;
 		next.customText = undefined;
 		return next;
 	}
+	next.customSelected = true;
 	next.customText = rawValue;
 	return next;
 }
 
+export function setCustomSelected(
+	answer: AskStateAnswer,
+	selected: boolean
+): AskStateAnswer {
+	const next = cloneAnswer(answer);
+	next.customSelected = selected || undefined;
+	return next;
+}
+
 export function saveQuestionNote(
 	answer: AskStateAnswer,
 	rawValue: string
@@ -137,7 +149,10 @@ export function isAnswerAnswered(answer?: AskStateAnswer): boolean {
 	if (!answer) {
 		return false;
 	}
-	return answer.selected.length > 0 || !!answer.customText?.trim();
+	return (
+		answer.selected.length > 0 ||
+		!!(answer.customSelected && answer.customText?.trim())
+	);
 }
 
 export function hasAnswerNotes(answer?: AskStateAnswer): boolean {
@@ -178,13 +193,16 @@ export function isOptionSelected(
 }
 
 export function serializeAnswer(answer: AskStateAnswer): AskResultAnswer {
+	const selectedCustomText = answer.customSelected
+		? answer.customText
+		: undefined;
 	const values = [
 		...answer.selected.map((selection) => selection.value),
-		...(answer.customText ? [answer.customText] : []),
+		...(selectedCustomText ? [selectedCustomText] : []),
 	];
 	const labels = [
 		...answer.selected.map((selection) => selection.label),
-		...(answer.customText ? [answer.customText] : []),
+		...(selectedCustomText ? [selectedCustomText] : []),
 	];
 	const indices = answer.selected.map((selection) => selection.index);
 	const selectedNotes = answer.optionNotes
@@ -202,7 +220,7 @@ export function serializeAnswer(answer: AskStateAnswer): AskResultAnswer {
 		values,
 		labels,
 		indices,
-		customText: answer.customText,
+		customText: selectedCustomText,
 		note: answer.note,
 		optionNotes:
 			selectedNotes && Object.keys(selectedNotes).length > 0
diff --git a/src/state/transitions.ts b/src/state/transitions.ts
index e22e19f..b7d35ad 100644
--- a/src/state/transitions.ts
+++ b/src/state/transitions.ts
@@ -6,6 +6,7 @@ import {
 	saveCustomText,
 	saveOptionNote,
 	saveQuestionNote,
+	setCustomSelected,
 	setSingleSelection,
 	toggleSelection,
 } from "./answers.ts";
@@ -187,7 +188,7 @@ function activateCurrentOption(
 		return state;
 	}
 	if (option.isCustomOption) {
-		return setView(state, inputView(question.id));
+		return activateCustomOption(state, question.id, question.type, trigger);
 	}
 	if (question.type === "multi") {
 		if (trigger === "confirm") {
@@ -215,6 +216,23 @@ function activateCurrentOption(
 	return trigger === "toggle" ? nextState : advanceToNextTab(nextState);
 }
 
+function activateCustomOption(
+	state: AskState,
+	questionId: string,
+	questionType: AskState["questions"][number]["type"],
+	trigger: "toggle" | "confirm" | "digit"
+): AskState {
+	if (questionType === "multi" && trigger !== "confirm") {
+		const answer = getAnswer(state, questionId);
+		if (answer?.customText?.trim()) {
+			return updateAnswer(state, questionId, (currentAnswer) =>
+				setCustomSelected(currentAnswer, !answer.customSelected)
+			);
+		}
+	}
+	return setView(state, inputView(questionId));
+}
+
 function saveInputValue(
 	state: AskState,
 	rawValue: string,
@@ -239,7 +257,10 @@ function saveInputValue(
 				question.type === "multi" ? "multi" : "single"
 			)
 	);
-	if (!(submit && isAnswerAnswered(nextState.answers[question.id]))) {
+	if (
+		question.type === "multi" ||
+		!(submit && isAnswerAnswered(nextState.answers[question.id]))
+	) {
 		return nextState;
 	}
 	return advanceToNextTab(nextState);
diff --git a/src/types.ts b/src/types.ts
index b21500c..ca70dbd 100644
--- a/src/types.ts
+++ b/src/types.ts
@@ -46,6 +46,7 @@ export interface AskSelectedOption {
 }
 
 export interface AskStateAnswer {
+	customSelected?: boolean;
 	customText?: string;
 	note?: string;
 	optionNotes?: Record<string, string>;
diff --git a/src/ui/view-models/question.ts b/src/ui/view-models/question.ts
index cfd7cf4..a4a9e9b 100644
--- a/src/ui/view-models/question.ts
+++ b/src/ui/view-models/question.ts
@@ -88,7 +88,7 @@ function buildOptionRowModel(
 	const answer = getAnswer(state, question.id);
 	const selected = index === state.activeOptionIndex;
 	const answered = option.isCustomOption
-		? !!answer?.customText
+		? !!(answer?.customSelected && answer.customText?.trim())
 		: isOptionSelected(answer, option.value);
 	const pointer = getOptionPointer(option, selected);
 	return {
@@ -180,10 +180,10 @@ function getPreviewLayout(
 
 function getOptionPrefix(
 	questionType: QuestionRenderContext["question"]["type"],
-	option: AskDisplayOption,
+	_option: AskDisplayOption,
 	answered: boolean
 ): string {
-	if (questionType !== "multi" || option.isCustomOption) {
+	if (questionType !== "multi") {
 		return "";
 	}
 	return `[${answered ? "x" : " "}] `;
diff --git a/tests/question-view-model.test.ts b/tests/question-view-model.test.ts
index 966b6cc..d44d919 100644
--- a/tests/question-view-model.test.ts
+++ b/tests/question-view-model.test.ts
@@ -5,6 +5,7 @@ import { getRenderableOptions } from "../src/state/selectors.ts";
 import {
 	applyNumberShortcut,
 	enterQuestionNoteMode,
+	submitCustomAnswer,
 } from "../src/state/transitions.ts";
 import { buildQuestionScreenModel } from "../src/ui/view-models/question.ts";
 
@@ -55,6 +56,26 @@ test("question view model marks active custom option as inline editor", () => {
 	assert.equal(model.rows[1]?.detail?.placeholder, "Type answer...");
 });
 
+test("question view model marks multi custom answer as checked", () => {
+	let state = createInitialState({
+		questions: [
+			{
+				id: "q1",
+				prompt: "Pick many",
+				type: "multi",
+				options: [{ value: "a", label: "A" }],
+			},
+		],
+	});
+	state = applyNumberShortcut(state, 2);
+	state = submitCustomAnswer(state, "Other answer");
+
+	const model = buildQuestionScreenModel(buildContext(state));
+	assert.equal(model.rows[1]?.prefix, "[x] ");
+	assert.equal(model.rows[1]?.color, "success");
+	assert.equal(model.rows[1]?.detail?.kind, "custom-text");
+});
+
 test("question view model exposes saved question notes", () => {
 	let state = enterQuestionNoteMode(
 		createInitialState({
diff --git a/tests/state.test.ts b/tests/state.test.ts
index 7a55841..50dfff7 100644
--- a/tests/state.test.ts
+++ b/tests/state.test.ts
@@ -390,7 +390,7 @@ test("multi-select keeps existing selections when leaving custom input empty", (
 	assert.equal(state.answers.q1.customText, undefined);
 });
 
-test("multi-select keeps existing selections when saving custom text", () => {
+test("multi-select keeps existing selections and stays on tab when submitting custom text", () => {
 	let state = createInitialState({
 		questions: [
 			{
@@ -414,7 +414,8 @@ test("multi-select keeps existing selections when saving custom text", () => {
 	state = applyNumberShortcut(state, 3);
 	state = submitCustomAnswer(state, "SolidStart");
 
-	assert.equal(state.activeTabIndex, 1);
+	assert.equal(state.activeTabIndex, 0);
+	assert.equal(state.view.kind, "navigate");
 	assert.deepEqual(
 		state.answers.q1.selected.map((selection) => selection.value),
 		["react"]
@@ -541,6 +542,43 @@ test("deselecting an option keeps its note in state but omits it from submission
 	});
 });
 
+test("multi-select toggles saved custom text selection with space or number shortcuts", () => {
+	let state = createInitialState({
+		questions: [
+			{
+				id: "q1",
+				prompt: "Pick frameworks",
+				type: "multi",
+				options: [{ value: "react", label: "React" }],
+			},
+		],
+	});
+
+	state = applyNumberShortcut(state, 2);
+	state = submitCustomAnswer(state, "SolidStart");
+	assert.equal(state.answers.q1.customText, "SolidStart");
+	assert.equal(state.activeTabIndex, 0);
+
+	state = toggleCurrentMultiOption(state);
+	assert.equal(state.answers.q1.customText, "SolidStart");
+	assert.equal(state.answers.q1.customSelected, undefined);
+	assert.equal(toAskResult(state).answers.q1, undefined);
+	assert.equal(state.view.kind, "navigate");
+	assert.equal(state.activeTabIndex, 0);
+
+	state = applyNumberShortcut(state, 2);
+	assert.equal(state.answers.q1.customText, "SolidStart");
+	assert.equal(state.answers.q1.customSelected, true);
+	assert.equal(state.view.kind, "navigate");
+	assert.deepEqual(toAskResult(state).answers.q1?.values, ["SolidStart"]);
+
+	state = applyNumberShortcut(state, 2);
+	assert.equal(state.answers.q1.customText, "SolidStart");
+	assert.equal(state.answers.q1.customSelected, undefined);
+	assert.equal(state.view.kind, "navigate");
+	assert.equal(toAskResult(state).answers.q1, undefined);
+});
+
 test("multi-select keeps custom text when toggling additional options", () => {
 	let state = createInitialState({
 		questions: [