diff --git a/api/src/party/__tests__/question-generation.test.ts b/api/src/party/__tests__/question-generation.test.ts
index 3048bce..24713f7 100644
--- a/api/src/party/__tests__/question-generation.test.ts
+++ b/api/src/party/__tests__/question-generation.test.ts
@@ -6,10 +6,12 @@ import {
 	type PartyAnalytics,
 	type PartyQuestionMember,
 	pickQuestionCandidate,
+	selectQuestionSong,
 } from "../question-utils";
 import { buildSocialQuestion } from "../social-question-generator";
 
 type Db = typeof import("../../db").db;
+type Song = NonNullable<Question["song"]>;
 
 function makeChoiceQuestion(
 	text: string,
@@ -61,6 +63,39 @@ function createFakeDb(trackReleaseDate: Date | null) {
 	} as unknown as Db;
 }
 
+function makeSong(id: string, platformId: string, name: string): Song {
+	return {
+		id,
+		albumId: "album-1",
+		platform: "spotify",
+		platform_id: platformId,
+		name,
+		popularity: 1,
+		duration: 1,
+		explicit: false,
+		disc_number: 1,
+		track_number: 1,
+	};
+}
+
+function createSongFallbackDb(rows: Song[]) {
+	return {
+		query: {
+			topTrack: {
+				findMany: vi.fn(async () =>
+					rows.map((row, index) => ({
+						position: index + 1,
+						track: row,
+					})),
+				),
+			},
+			track: {
+				findMany: vi.fn(async () => []),
+			},
+		},
+	} as unknown as Db;
+}
+
 describe("question generation", () => {
 	it("skips repeated question keys, subjects, and text", () => {
 		const history: QuizRound[] = [
@@ -230,4 +265,79 @@ describe("question generation", () => {
 
 		expect(question).toBeNull();
 	});
+
+	it("selects a fresh party song when the current one was already used", async () => {
+		const db = createSongFallbackDb([
+			makeSong("track-1", "spotify:track:one", "One"),
+			makeSong("track-2", "spotify:track:two", "Two"),
+		]);
+		const question = {
+			type: "choice" as const,
+			text: "Which genre appears most in the party analytics?",
+			correct: 0,
+			startTimestamp: 1,
+			endTimestamp: 2,
+			points: 10,
+			options: ["A", "B"],
+			questionKey: "audio:genre:pop",
+			subjectKey: "genre:pop",
+		};
+
+		const song = await selectQuestionSong({
+			db,
+			analytics: null,
+			members: [{ userId: "a", name: "A" }],
+			history: [
+				{
+					questionIndex: 0,
+					question: {
+						...question,
+						song: makeSong("track-1", "spotify:track:one", "One"),
+					},
+					responses: [],
+				},
+			],
+			question,
+		});
+
+		expect(song?.platform_id).toBe("spotify:track:two");
+	});
+
+	it("keeps a song-target question on the same track", async () => {
+		const db = createSongFallbackDb([
+			makeSong("track-1", "spotify:track:one", "One"),
+			makeSong("track-2", "spotify:track:two", "Two"),
+		]);
+		const question = {
+			type: "choice" as const,
+			text: "What song is currently playing?",
+			correct: 0,
+			startTimestamp: 1,
+			endTimestamp: 2,
+			points: 10,
+			options: ["A", "B"],
+			questionKey: "audio:current-song:One",
+			subjectKey: "track:One",
+			hideSongTitle: true,
+			song: {
+				...makeSong("track-1", "spotify:track:one", "One"),
+			},
+		};
+
+		const song = await selectQuestionSong({
+			db,
+			analytics: null,
+			members: [{ userId: "a", name: "A" }],
+			history: [
+				{
+					questionIndex: 0,
+					question,
+					responses: [],
+				},
+			],
+			question,
+		});
+
+		expect(song?.platform_id).toBe("spotify:track:one");
+	});
 });
diff --git a/api/src/party/__tests__/question-generator.test.ts b/api/src/party/__tests__/question-generator.test.ts
index 5aef0f7..f8fb12f 100644
--- a/api/src/party/__tests__/question-generator.test.ts
+++ b/api/src/party/__tests__/question-generator.test.ts
@@ -1,5 +1,6 @@
 import { describe, expect, it, vi } from "vitest";
 import type { QuizState } from "../../party-types";
+import * as audioQuestionGenerator from "../audio-question-generator";
 
 vi.mock("../audio-question-generator", () => ({
 	buildAudioMetadataQuestion: vi.fn(async () => null),
@@ -47,4 +48,59 @@ describe("generatePartyQuestion", () => {
 
 		expect(question).toBeNull();
 	});
+
+	it("attaches a fallback song to generated questions", async () => {
+		vi.mocked(
+			audioQuestionGenerator.buildAudioMetadataQuestion,
+		).mockResolvedValueOnce({
+			type: "choice",
+			text: "Which genre appears most in the party analytics?",
+			correct: 0,
+			startTimestamp: 1,
+			endTimestamp: 2,
+			points: 10,
+			options: ["A", "B"],
+			questionKey: "audio:genre:pop",
+			subjectKey: "genre:pop",
+		});
+
+		const quizState = {
+			status: "running",
+			workflowId: null,
+			questionIndex: 0,
+			currentQuestion: null,
+			answers: {},
+			scores: {},
+			history: [],
+		} as QuizState;
+
+		const question = await generatePartyQuestion({
+			db: {
+				query: {
+					partyMember: {
+						findMany: vi.fn(async () => [{ userId: "a", user: { name: "A" } }]),
+					},
+					topTrack: {
+						findMany: vi.fn(async () => [
+							{
+								position: 1,
+								track: {
+									id: "track-1",
+									platform: "spotify",
+									platform_id: "spotify:track:one",
+									name: "One",
+								},
+							},
+						]),
+					},
+				},
+			} as never,
+			partyId: "party-1",
+			quizState,
+			analytics: null,
+			index: 0,
+		});
+
+		expect(question?.song?.platform_id).toBe("spotify:track:one");
+	});
 });
diff --git a/api/src/party/question-generator.ts b/api/src/party/question-generator.ts
index 1a44d42..f6eec91 100644
--- a/api/src/party/question-generator.ts
+++ b/api/src/party/question-generator.ts
@@ -2,8 +2,11 @@ import type { db } from "../db";
 import type { Question, QuizState } from "../party-types";
 import { buildAudioMetadataQuestion } from "./audio-question-generator";
 import { buildNumericQuestion } from "./numeric-question-generator";
-import type { PartyAnalytics } from "./question-utils";
-import { fetchPartyMembers } from "./question-utils";
+import {
+	fetchPartyMembers,
+	type PartyAnalytics,
+	selectQuestionSong,
+} from "./question-utils";
 import { buildSocialQuestion } from "./social-question-generator";
 
 export type PartyQuestionType = "audio-metadata" | "social" | "numeric";
@@ -36,37 +39,44 @@ export async function generatePartyQuestion({
 	];
 
 	for (const type of typeOrder) {
+		let question: Question | null = null;
 		if (type === "audio-metadata") {
-			const q = await buildAudioMetadataQuestion(
+			question = await buildAudioMetadataQuestion(
 				dbClient,
 				analytics,
 				index,
 				quizState.history,
 			);
-			if (q) return q;
-			continue;
-		}
-
-		if (type === "social") {
-			const q = await buildSocialQuestion(
+		} else if (type === "social") {
+			question = await buildSocialQuestion(
 				dbClient,
 				quizState,
 				analytics,
 				members,
 				index,
 			);
-			if (q) return q;
+		} else {
+			question = await buildNumericQuestion({
+				db: dbClient,
+				analytics,
+				index,
+				members,
+				history: quizState.history,
+			});
+		}
+
+		if (!question) {
 			continue;
 		}
 
-		const q = await buildNumericQuestion({
+		const song = await selectQuestionSong({
 			db: dbClient,
 			analytics,
-			index,
 			members,
 			history: quizState.history,
+			question,
 		});
-		if (q) return q;
+		return song ? { ...question, song } : question;
 	}
 
 	return null;
diff --git a/api/src/party/question-utils.ts b/api/src/party/question-utils.ts
index af51e04..f0cbdb3 100644
--- a/api/src/party/question-utils.ts
+++ b/api/src/party/question-utils.ts
@@ -1,7 +1,7 @@
 import type { InferSelectModel } from "drizzle-orm";
 import type { db as Db } from "../db";
 import type { track as trackTable } from "../db/schema";
-import type { QuizRound } from "../party-types";
+import type { Question, QuizRound } from "../party-types";
 
 export type PartyQuestionMember = {
 	userId: string;
@@ -262,6 +262,228 @@ export async function resolveQuestionSong(
 	return song;
 }
 
+type SongSelectionInput = {
+	db: typeof Db;
+	analytics: PartyAnalytics;
+	members: PartyQuestionMember[];
+	history: QuizRound[];
+	question: Question;
+};
+
+export async function selectQuestionSong({
+	db,
+	analytics,
+	members,
+	history,
+	question,
+}: SongSelectionInput): Promise<QuestionSong | null> {
+	const keepSpecificSong = isSongTargetQuestion(question);
+	const usedPlatformIds = new Set(
+		history
+			.map((round) => round.question.song?.platform_id)
+			.filter((value): value is string => isUsableText(value)),
+	);
+
+	const candidates = await collectSongCandidates({
+		db,
+		analytics,
+		members,
+		question,
+	});
+
+	if (candidates.length === 0) return question.song ?? null;
+	if (keepSpecificSong) return candidates[0] ?? question.song ?? null;
+
+	const freshCandidate = candidates.find(
+		(candidate) =>
+			isUsableText(candidate.platform_id) &&
+			!usedPlatformIds.has(candidate.platform_id),
+	);
+	return freshCandidate ?? candidates[0] ?? question.song ?? null;
+}
+
+async function collectSongCandidates({
+	db,
+	analytics,
+	members,
+	question,
+}: {
+	db: typeof Db;
+	analytics: PartyAnalytics;
+	members: PartyQuestionMember[];
+	question: Question;
+}): Promise<QuestionSong[]> {
+	const candidates: QuestionSong[] = [];
+	const seen = new Set<string>();
+	const push = (song: QuestionSong | null | undefined) => {
+		if (!song || !isUsableText(song.platform_id)) return;
+		if (seen.has(song.platform_id)) return;
+		seen.add(song.platform_id);
+		candidates.push(song);
+	};
+
+	push(question.song);
+
+	const subjectSong = await resolveSongFromQuestionSubject(
+		db,
+		analytics,
+		question,
+	);
+	push(subjectSong);
+
+	const peopleSong = await resolveSongFromMentionedPeople(
+		db,
+		analytics,
+		question,
+	);
+	push(peopleSong);
+
+	const topClusterTracks = [...(analytics?.storyClusters?.[0]?.tracks ?? [])]
+		.filter((track) => isUsableText(track.name))
+		.sort((a, b) => getTrackScore(b) - getTrackScore(a));
+
+	for (const track of topClusterTracks) {
+		const song = await resolveQuestionSong(db, analytics, {
+			trackName: track.name,
+			artistNames: track.artists?.map((artist) => artist.name),
+			albumName: track.albumName,
+		});
+		push(song);
+	}
+
+	if (members.length > 0) {
+		const topPartySongs = await fetchPartyTopSongs(db, members);
+		for (const song of topPartySongs) {
+			push(song);
+		}
+	}
+
+	return candidates;
+}
+
+async function resolveSongFromQuestionSubject(
+	db: typeof Db,
+	analytics: PartyAnalytics,
+	question: Question,
+): Promise<QuestionSong | null> {
+	const subjectKey = question.subjectKey ?? "";
+	if (subjectKey.startsWith("track:")) {
+		const trackName = subjectKey.slice("track:".length).trim();
+		if (!trackName) return null;
+		return resolveQuestionSong(db, analytics, { trackName });
+	}
+
+	if (subjectKey.startsWith("artist:")) {
+		const artistName = subjectKey.slice("artist:".length).trim();
+		if (!artistName) return null;
+		return resolveQuestionSong(db, analytics, { artistNames: [artistName] });
+	}
+
+	return null;
+}
+
+async function resolveSongFromMentionedPeople(
+	db: typeof Db,
+	analytics: PartyAnalytics,
+	question: Question,
+): Promise<QuestionSong | null> {
+	const subjectKey = question.subjectKey ?? "";
+	const userIds = subjectKey.startsWith("member:")
+		? [subjectKey.slice("member:".length).trim()].filter(Boolean)
+		: subjectKey.startsWith("pair:")
+			? subjectKey
+					.slice("pair:".length)
+					.split("|")
+					.map((value) => value.trim())
+					.filter(Boolean)
+			: [];
+
+	if (userIds.length === 0) return null;
+
+	const tracks = [...(analytics?.storyClusters?.[0]?.tracks ?? [])]
+		.filter((track) => isUsableText(track.name))
+		.sort(
+			(a, b) =>
+				getMemberTrackScore(b, userIds) - getMemberTrackScore(a, userIds),
+		);
+
+	for (const track of tracks) {
+		const song = await resolveQuestionSong(db, analytics, {
+			trackName: track.name,
+			artistNames: track.artists?.map((artist) => artist.name),
+			albumName: track.albumName,
+		});
+		if (song) return song;
+	}
+
+	return null;
+}
+
+async function fetchPartyTopSongs(
+	db: typeof Db,
+	members: PartyQuestionMember[],
+): Promise<QuestionSong[]> {
+	const songs: QuestionSong[] = [];
+	const seen = new Set<string>();
+
+	for (const member of members) {
+		const rows = await db.query.topTrack.findMany({
+			where: {
+				userId: member.userId,
+			},
+			with: {
+				track: {
+					with: {
+						album: true,
+						artists: true,
+					},
+				},
+			},
+			orderBy: {
+				position: "asc",
+			},
+			limit: 5,
+		});
+
+		for (const row of rows) {
+			const song = row.track;
+			if (!song || !isUsableText(song.platform_id)) continue;
+			if (seen.has(song.platform_id)) continue;
+			seen.add(song.platform_id);
+			songs.push(song);
+		}
+	}
+
+	return songs;
+}
+
+function isSongTargetQuestion(question: Question): boolean {
+	const key = question.questionKey?.toLowerCase() ?? "";
+	const text = question.text.toLowerCase();
+	return (
+		question.hideSongTitle === true ||
+		key.startsWith("audio:current-song:") ||
+		text.includes("what song") ||
+		text.includes("which song")
+	);
+}
+
+function getTrackScore(track: { memberScores?: { score: number }[] }): number {
+	return (track.memberScores ?? []).reduce(
+		(total, entry) => total + entry.score,
+		0,
+	);
+}
+
+function getMemberTrackScore(
+	track: { memberScores?: { userId: string; score: number }[] },
+	userIds: string[],
+): number {
+	return (track.memberScores ?? []).reduce((total, entry) => {
+		return userIds.includes(entry.userId) ? total + entry.score : total;
+	}, 0);
+}
+
 export function isUsableText(
 	value: string | null | undefined,
 ): value is string {