diff --git a/packages/bot/src/functions/music/commands/nowplaying.spec.ts b/packages/bot/src/functions/music/commands/nowplaying.spec.ts
index e7b535e4a..f28a8c64c 100644
--- a/packages/bot/src/functions/music/commands/nowplaying.spec.ts
+++ b/packages/bot/src/functions/music/commands/nowplaying.spec.ts
@@ -5,7 +5,7 @@ const requireQueueMock = jest.fn()
 const requireCurrentTrackMock = jest.fn()
 const interactionReplyMock = jest.fn()
 const resolveGuildQueueMock = jest.fn()
-const trackToDataMock = jest.fn((track: unknown) => ({
+const playerTrackToDataMock = jest.fn((track: unknown) => ({
     title: (track as { title: string }).title,
 }))
 const buildTrackEmbedMock = jest.fn(() => ({ embed: 'nowplaying' }))
@@ -25,7 +25,7 @@ jest.mock('../../../utils/music/queueResolver', () => ({
 }))
 
 jest.mock('../../../utils/general/responseEmbeds', () => ({
-    trackToData: (...args: unknown[]) => trackToDataMock(...args),
+    playerTrackToData: (...args: unknown[]) => playerTrackToDataMock(...args),
     buildTrackEmbed: (...args: unknown[]) => buildTrackEmbedMock(...args),
 }))
 
@@ -89,7 +89,7 @@ describe('nowplaying command', () => {
             interaction: makeInteraction(),
         } as any)
 
-        expect(trackToDataMock).toHaveBeenCalledWith(track)
+        expect(playerTrackToDataMock).toHaveBeenCalledWith(track)
         expect(createProgressBar).toHaveBeenCalledWith({
             length: 18,
             timecodes: true,
diff --git a/packages/bot/src/functions/music/commands/songinfo.ts b/packages/bot/src/functions/music/commands/songinfo.ts
index 2226500f9..eb0fb2ccb 100644
--- a/packages/bot/src/functions/music/commands/songinfo.ts
+++ b/packages/bot/src/functions/music/commands/songinfo.ts
@@ -4,7 +4,7 @@ import { assertDefined } from '@lucky/shared/utils/guards'
 import { interactionReply } from '../../../utils/general/interactionReply'
 import {
     buildTrackEmbed,
-    trackToData,
+    playerTrackToData,
 } from '../../../utils/general/responseEmbeds'
 import type { CommandExecuteParams } from '../../../types/CommandData'
 import {
@@ -27,7 +27,7 @@ export default new Command({
         if (!(await requireQueue(queue, interaction))) return
         if (!(await requireCurrentTrack(queue, interaction))) return
 
-        const trackData = trackToData(
+        const trackData = playerTrackToData(
             assertDefined(
                 track,
                 'track present after requireCurrentTrack guard',
diff --git a/packages/bot/src/handlers/webMusic/mappers.spec.ts b/packages/bot/src/handlers/webMusic/mappers.spec.ts
index b85eeba90..6be844e8f 100644
--- a/packages/bot/src/handlers/webMusic/mappers.spec.ts
+++ b/packages/bot/src/handlers/webMusic/mappers.spec.ts
@@ -81,6 +81,20 @@ describe('mapTrack', () => {
         const track = mapTrack(makeRawTrack({ requestedBy: null }))
         expect(track.requestedBy).toBeUndefined()
     })
+
+    it('forwards recommendationReason from track metadata', () => {
+        const track = mapTrack(
+            makeRawTrack({
+                metadata: { isAutoplay: true, recommendationReason: 'similar vibes' },
+            }),
+        )
+        expect(track.recommendationReason).toBe('similar vibes')
+    })
+
+    it('omits recommendationReason when metadata has none', () => {
+        const track = mapTrack(makeRawTrack({ metadata: { isAutoplay: true } }))
+        expect(track.recommendationReason).toBeUndefined()
+    })
 })
 
 describe('repeatModeToString', () => {
diff --git a/packages/bot/src/handlers/webMusic/mappers.ts b/packages/bot/src/handlers/webMusic/mappers.ts
index b68763a72..7ea50b5b8 100644
--- a/packages/bot/src/handlers/webMusic/mappers.ts
+++ b/packages/bot/src/handlers/webMusic/mappers.ts
@@ -16,11 +16,18 @@ interface RawTrack {
     durationMS: number
     requestedBy?: { username?: string } | null
     source?: string
+    metadata?: {
+        isAutoplay?: boolean
+        recommendationReason?: string
+    } | null
 }
 
 const KNOWN_SOURCES = ['youtube', 'spotify', 'soundcloud']
 
 export function mapTrack(track: RawTrack): TrackInfo {
+    const rawReason = track.metadata?.recommendationReason
+    const reason =
+        typeof rawReason === 'string' ? rawReason : undefined
     return {
         id: track.id,
         title: track.title,
@@ -33,6 +40,7 @@ export function mapTrack(track: RawTrack): TrackInfo {
         source: (KNOWN_SOURCES.includes(track.source ?? '')
             ? track.source
             : 'unknown') as TrackInfo['source'],
+        ...(reason ? { recommendationReason: reason } : {}),
     }
 }
 
diff --git a/packages/bot/src/utils/general/responseEmbeds/buildTrackEmbed.spec.ts b/packages/bot/src/utils/general/responseEmbeds/buildTrackEmbed.spec.ts
index dcaaee1da..1b2003446 100644
--- a/packages/bot/src/utils/general/responseEmbeds/buildTrackEmbed.spec.ts
+++ b/packages/bot/src/utils/general/responseEmbeds/buildTrackEmbed.spec.ts
@@ -2,6 +2,7 @@ import { describe, it, expect } from '@jest/globals'
 import {
     buildTrackEmbed,
     buildCommandTrackEmbed,
+    playerTrackToData,
     trackToData,
 } from './buildTrackEmbed'
 import { detectSource } from '../../music/nowPlayingEmbed'
@@ -67,6 +68,16 @@ describe('buildTrackEmbed', () => {
         expect(progress?.inline).toBe(false)
     })
 
+    it('adds a Why this track field when recommendationReason is set', () => {
+        const embed = buildTrackEmbed(
+            { ...baseTrack, recommendationReason: 'similar vibes' },
+            'playing',
+            fakeUser,
+        )
+        const why = embed.data.fields?.find((f) => f.name === 'Why this track')
+        expect(why?.value).toBe('similar vibes')
+    })
+
     it('omits the Progress field when no/null progress bar', () => {
         const noOpts = buildTrackEmbed(baseTrack, 'playing', fakeUser)
         const nullBar = buildTrackEmbed(baseTrack, 'playing', fakeUser, {
@@ -134,7 +145,7 @@ describe('trackToData', () => {
     }
 
     it('maps all fields and formats duration correctly', () => {
-        const data = trackToData(fakeTrack as never)
+        const data = trackToData(fakeTrack)
         expect(data.title).toBe('Test Song')
         expect(data.author).toBe('Test Artist')
         expect(data.url).toBe(fakeTrack.url)
@@ -143,17 +154,33 @@ describe('trackToData', () => {
         expect(data.duration).toBe('3:35')
     })
 
+    it('forwards recommendationReason from track metadata', () => {
+        const data = trackToData({
+            ...fakeTrack,
+            metadata: { recommendationReason: 'same artist' },
+        })
+        expect(data.recommendationReason).toBe('same artist')
+    })
+
+    it('rejects invalid recommendation metadata from discord-player', () => {
+        const data = playerTrackToData({
+            ...fakeTrack,
+            metadata: { recommendationReason: 123 },
+        })
+        expect(data.recommendationReason).toBeUndefined()
+    })
+
     it.each([
         [0, undefined],
         [65000, '1:05'],
     ])('handles edge cases: durationMS=%i → %s', (durationMS, expected) => {
-        const data = trackToData({ ...fakeTrack, durationMS } as never)
+        const data = trackToData({ ...fakeTrack, durationMS })
         expect(data.duration).toBe(expected)
         if (durationMS === 0) {
             const noSource = trackToData({
                 ...fakeTrack,
                 source: undefined,
-            } as never)
+            })
             expect(noSource.source).toBeNull()
         }
     })
@@ -170,11 +197,7 @@ describe('buildCommandTrackEmbed', () => {
     }
 
     it('builds embed with status label and track data', () => {
-        const embed = buildCommandTrackEmbed(
-            track as never,
-            '⏸️ Paused',
-            fakeUser,
-        )
+        const embed = buildCommandTrackEmbed(track, '⏸️ Paused', fakeUser)
         expect(embed.data.author?.name).toBe('⏸️ Paused')
         expect(embed.data.title).toBe(track.title)
         expect(embed.data.footer?.text).toContain(fakeUser.tag)
diff --git a/packages/bot/src/utils/general/responseEmbeds/buildTrackEmbed.ts b/packages/bot/src/utils/general/responseEmbeds/buildTrackEmbed.ts
index 59276af5f..3ce20b4d2 100644
--- a/packages/bot/src/utils/general/responseEmbeds/buildTrackEmbed.ts
+++ b/packages/bot/src/utils/general/responseEmbeds/buildTrackEmbed.ts
@@ -1,6 +1,7 @@
 import { EmbedBuilder } from 'discord.js'
 import type { User } from 'discord.js'
 import type { Track } from 'discord-player'
+import type { TrackMetadata } from '@lucky/shared/types'
 import { detectSource } from '../../music/nowPlayingEmbed'
 import { trackSource } from '../../music/trackFields'
 import { formatDurationClock } from '../formatDuration'
@@ -14,6 +15,8 @@ export type TrackData = {
     thumbnail?: string
     duration?: string
     source?: string | null
+    /** Why autoplay picked this track, when present. */
+    recommendationReason?: string
 }
 
 const KIND_LABELS: Record<TrackEmbedKind, string> = {
@@ -23,6 +26,18 @@ const KIND_LABELS: Record<TrackEmbedKind, string> = {
     history: 'From History',
 }
 
+type TrackDataSource = Pick<
+    Track<TrackMetadata>,
+    'title' | 'author' | 'url' | 'thumbnail' | 'durationMS' | 'source'
+> &
+    Partial<Pick<Track<TrackMetadata>, 'metadata'>>
+
+type PlayerTrackDataSource = Pick<
+    Track<unknown>,
+    'title' | 'author' | 'url' | 'thumbnail' | 'durationMS' | 'source'
+> &
+    Partial<Pick<Track<unknown>, 'metadata'>>
+
 export type TrackEmbedOptions = {
     /**
      * A pre-rendered playback progress bar (e.g. discord-player's
@@ -66,6 +81,20 @@ export function buildTrackEmbed(
     }
     fields.push({ name: 'Source', value: badge.label, inline: true })
 
+    if (track.recommendationReason) {
+        // Discord embed field values cap at 1024; open-ended autoplay signals
+        // from Last.fm/Spotify can theoretically exceed that and drop the embed.
+        const reason =
+            track.recommendationReason.length > 1024
+                ? `${track.recommendationReason.slice(0, 1021)}...`
+                : track.recommendationReason
+        fields.push({
+            name: 'Why this track',
+            value: reason,
+            inline: false,
+        })
+    }
+
     if (options?.progressBar) {
         fields.push({
             name: 'Progress',
@@ -79,17 +108,31 @@ export function buildTrackEmbed(
 }
 
 export function buildCommandTrackEmbed(
-    track: Track,
+    track: PlayerTrackDataSource,
     statusLabel: string,
     requestedBy: Pick<User, 'tag' | 'displayAvatarURL'>,
 ): ReturnType<typeof buildTrackEmbed> {
-    const trackData = trackToData(track)
+    const trackData = playerTrackToData(track)
     const embed = buildTrackEmbed(trackData, 'playing', requestedBy)
     embed.setAuthor({ name: statusLabel })
     return embed
 }
 
-export function trackToData(track: Track): TrackData {
+export function playerTrackToData(track: PlayerTrackDataSource): TrackData {
+    return trackToData({
+        title: track.title,
+        author: track.author,
+        url: track.url,
+        thumbnail: track.thumbnail,
+        durationMS: track.durationMS,
+        source: track.source,
+        metadata: normalizeTrackMetadata(track.metadata),
+    })
+}
+
+export function trackToData(track: TrackDataSource): TrackData {
+    const recommendationReason = track.metadata?.recommendationReason
+
     return {
         title: track.title,
         author: track.author,
@@ -99,5 +142,19 @@ export function trackToData(track: Track): TrackData {
             ? formatDurationClock(Math.floor(track.durationMS / 1000))
             : undefined,
         source: trackSource(track) ?? null,
+        ...(recommendationReason ? { recommendationReason } : {}),
     }
 }
+
+function normalizeTrackMetadata(metadata: unknown): TrackMetadata | null {
+    if (
+        typeof metadata !== 'object' ||
+        metadata === null ||
+        !('recommendationReason' in metadata) ||
+        typeof metadata.recommendationReason !== 'string'
+    ) {
+        return null
+    }
+
+    return { recommendationReason: metadata.recommendationReason }
+}
diff --git a/packages/bot/src/utils/general/responseEmbeds/index.ts b/packages/bot/src/utils/general/responseEmbeds/index.ts
index 93a1f50c7..089b45ebd 100644
--- a/packages/bot/src/utils/general/responseEmbeds/index.ts
+++ b/packages/bot/src/utils/general/responseEmbeds/index.ts
@@ -1,6 +1,7 @@
 export {
     buildTrackEmbed,
     buildCommandTrackEmbed,
+    playerTrackToData,
     trackToData,
     type TrackEmbedKind,
     type TrackData,
diff --git a/packages/bot/src/utils/music/trackFields.ts b/packages/bot/src/utils/music/trackFields.ts
index 95c2a5c17..ae3000cb4 100644
--- a/packages/bot/src/utils/music/trackFields.ts
+++ b/packages/bot/src/utils/music/trackFields.ts
@@ -16,7 +16,9 @@ import type { Track, TrackSource } from 'discord-player'
  * {@link TrackSource} union. Returns `undefined` when the source is absent at
  * runtime so callers keep their existing fallbacks.
  */
-export function trackSource(track: Track): TrackSource | undefined {
+export function trackSource(
+    track: Pick<Track, 'source'>,
+): TrackSource | undefined {
     const source: unknown = track.source
     return typeof source === 'string' ? (source as TrackSource) : undefined
 }
diff --git a/packages/frontend/src/components/Music/QueueList.test.tsx b/packages/frontend/src/components/Music/QueueList.test.tsx
index 8ed2edef3..2a8a64247 100644
--- a/packages/frontend/src/components/Music/QueueList.test.tsx
+++ b/packages/frontend/src/components/Music/QueueList.test.tsx
@@ -78,6 +78,21 @@ describe('QueueList', () => {
         expect(screen.getByText('(3 tracks)')).toBeInTheDocument()
     })
 
+    test('shows recommendationReason when present on a track', () => {
+        const tracks = makeTracks(1)
+        tracks[0].recommendationReason = 'similar vibes'
+        render(
+            <QueueList
+                tracks={tracks}
+                onRemove={onRemove}
+                onMove={onMove}
+                onClear={onClear}
+            />,
+        )
+
+        expect(screen.getByText('similar vibes')).toBeInTheDocument()
+    })
+
     test('shows singular track count for 1 track', () => {
         render(
             <QueueList
diff --git a/packages/frontend/src/components/Music/QueueList.tsx b/packages/frontend/src/components/Music/QueueList.tsx
index c221e4fba..3c5ba4d30 100644
--- a/packages/frontend/src/components/Music/QueueList.tsx
+++ b/packages/frontend/src/components/Music/QueueList.tsx
@@ -225,6 +225,14 @@ const QueueItem = memo(function QueueItem({
                 <p className='type-meta text-lucky-text-secondary truncate'>
                     {track.author}
                 </p>
+                {track.recommendationReason ? (
+                    <p
+                        className='type-meta text-lucky-text-tertiary truncate'
+                        title={track.recommendationReason}
+                    >
+                        {track.recommendationReason}
+                    </p>
+                ) : null}
             </div>
 
             <span className='type-meta text-lucky-text-secondary tabular-nums shrink-0 hidden sm:block'>
diff --git a/packages/frontend/src/pages/Music.tsx b/packages/frontend/src/pages/Music.tsx
index 952796e13..5ec4440e5 100644
--- a/packages/frontend/src/pages/Music.tsx
+++ b/packages/frontend/src/pages/Music.tsx
@@ -157,7 +157,9 @@ function NowPlayingHero({
     onVolumeChange: (v: number) => void
 }) {
     const { t } = useTranslation()
-    const currentTrack = state.tracks[0]
+    // Prefer the live currentTrack from SSE; fall back to the head of the
+    // upcoming queue for older state payloads that only filled tracks[].
+    const currentTrack = state.currentTrack ?? state.tracks[0]
 
     if (!currentTrack) {
         return (
@@ -208,9 +210,16 @@ function NowPlayingHero({
                             <h2 className='type-h2 text-lucky-text-primary mb-1 line-clamp-2'>
                                 {currentTrack.title || t('music.unknown')}
                             </h2>
-                            <p className='type-body text-lucky-text-secondary mb-4'>
+                            <p className='type-body text-lucky-text-secondary mb-1'>
                                 {currentTrack.author || t('music.unknown')}
                             </p>
+                            {currentTrack.recommendationReason ? (
+                                <p className='type-body-sm text-lucky-text-tertiary mb-4 line-clamp-2'>
+                                    {currentTrack.recommendationReason}
+                                </p>
+                            ) : (
+                                <div className='mb-4' />
+                            )}
                         </div>
 
                         <div>
diff --git a/packages/frontend/src/types/music.ts b/packages/frontend/src/types/music.ts
index 8002e8379..107cf9b57 100644
--- a/packages/frontend/src/types/music.ts
+++ b/packages/frontend/src/types/music.ts
@@ -8,6 +8,8 @@ export interface TrackInfo {
     durationFormatted: string
     requestedBy?: string
     source: 'youtube' | 'spotify' | 'soundcloud' | 'unknown'
+    /** Why autoplay picked this track, when present. */
+    recommendationReason?: string
 }
 
 export interface QueueState {
diff --git a/packages/shared/src/types/music.ts b/packages/shared/src/types/music.ts
index a86769bc3..fc0915700 100644
--- a/packages/shared/src/types/music.ts
+++ b/packages/shared/src/types/music.ts
@@ -8,6 +8,7 @@ export interface TrackMetadata {
     isAutoplay?: boolean
     source?: string
     engine?: string
+    recommendationReason?: string
 }
 
 export interface TrackTimestamp {