How Streamless works.
Everything you need to go from a pile of CDs and folders of music to a full iPod. If you're stuck on something this page doesn't cover, get in touch — it's a real person on the other end.
The short version: import your music (or rip your CDs), plug in your iPod, hit Sync. Streamless handles the rest — no iTunes, no Apple Music, no account.
Getting started
On first launch, Streamless offers two ways to fill your library. You can do either, both, or skip and come back later — everything is also available from the File menu.
- Import from Apple Music — brings over your existing Music.app library: tracks, playlists, play counts, ratings, and dates added. macOS will show one permission prompt ("Streamless wants to control Music") — click Allow, and that's the whole setup.
- Import files or folders — use File › Import Music… (⌘O) or just drag files and folders into the window. Streamless reads the tags and organizes everything by artist and album.
Importing your music
Streamless never moves or copies your files unless you ask it to. Imported music is referenced right where it lives — on your Mac, an external drive, wherever you keep it. Import is instant because nothing is being copied.
If you import from an external drive, Streamless asks whether to keep referencing the files there or copy them onto your Mac so they keep playing when the drive is unplugged. There's also a global "copy imported files" option in Settings if you prefer a managed library.
Supported formats: MP3, AAC, ALAC (Apple Lossless), FLAC, and WAV.
If a file goes missing (you moved or renamed it in Finder, or the drive is unplugged), Streamless tells you and offers to locate it — it never silently shows dead entries.
Importing from Apple Music
The Apple Music import preserves your play counts, ratings, dates added, and playlists. Two honest limitations, both Apple's, not ours:
- Apple Music streaming tracks and old DRM-protected purchases can't be imported. They aren't files you own, and they can't play on a classic iPod. Streamless detects them, skips them, and shows you a plain-language summary of what was skipped and why.
- Smart playlists import as regular playlists containing their current tracks — Apple doesn't expose the rules. You can rebuild them as native Streamless smart playlists in a couple of clicks (File › New Smart Playlist…).
Ripping CDs
Insert a CD and it appears in the sidebar within a few seconds, with the album name, track titles, and cover art looked up automatically from MusicBrainz. Click the disc, untick anything you don't want, and hit Rip.
Stop Apple Music opening every time you insert a CD. By default, macOS pops the disc up in Finder and opens Apple Music asking to import — every single time. To turn that off: open System Settings, scroll to the bottom of the left sidebar and click CDs & DVDs, then next to "When you insert a music CD" choose Ignore — or Open other application… and pick Streamless, so inserting a CD opens Streamless instead. (The CDs & DVDs item only appears while a disc drive is connected.)
- Format: AAC by default — small files, plays on every iPod. Switch to ALAC or FLAC (both lossless) right on the CD screen or in Settings › Audio.
- Where files go: ~/Music/Streamless by default, organized as Artist/Album. Change it on the CD screen or in Settings — an external drive works fine.
- You can preview tracks before ripping with the play button on each row, and cancel a rip partway through — finished tracks are kept.
- No match found? Rare pressings, bootlegs, and home-burned discs sometimes aren't in MusicBrainz. Click Edit Details… on the CD screen to type the album, artist, and track names yourself, and drag an image onto the disc's cover to set the art — then rip, and everything lands in your library under the names you gave it. (This works on recognized discs too, if a lookup got something wrong.)
Syncing your iPod
Plug your iPod in and it appears in the sidebar. Pick what to sync — everything, selected playlists, or manual — and hit Sync. Streamless writes the iPod's own database format directly; the iPod shows your music exactly as if iTunes had put it there.
- Supported iPods: iPod 1G–5G (including 5.5G), iPod Photo, iPod Mini, iPod Classic 6G/7G, and iPod Nano 1G–4G.
- Not supported: iPod Nano 6G/7G (Apple locked these — no third-party tool can write to them) and iPod Touch (it's an iOS device). The Nano 5G and iPod Shuffle aren't supported yet — Streamless can show you what's on them, but syncing is disabled with a note explaining why.
- Your iPod is safe. Before the first write, Streamless backs up the iPod's original database, and a sync can be cancelled any time before the final write — the iPod is left exactly as it was.
- Play counts and ratings sync both ways. Listen on the iPod, and those plays are merged back into your library on the next sync.
- FLAC tracks are skipped at sync for now — classic iPods can't play FLAC, and Streamless doesn't yet convert on the fly. The sync summary lists anything skipped and why. If your library is FLAC and an iPod is the goal, rip to ALAC instead (same lossless quality, iPod-native).
Playlists
Regular playlists work how you'd expect — create one with ⌘N, then right-click tracks to add them. Smart playlists (⌘⇧N) are rule-based and update themselves: "Genre is Jazz and Rating is at least 4," that kind of thing. When synced, a smart playlist lands on the iPod as a normal playlist holding whatever matched at sync time.
Album artwork
Art comes from three places, automatically: embedded art in your files, Cover Art Archive when you rip a CD, and a background lookup that fills in covers for any album missing one. If something's still missing, use File › Fetch Missing Album Art, or drag an image straight onto an album's cover to set it yourself.
Trial, buying, and activation
The free trial is 14 days, full-featured, no credit card, no account. When it ends, ripping, syncing, and playback pause — but your library stays visible and yours. Nothing is ever held hostage.
Buying is $29, one time, through the Buy button in the app. After checkout you get an activation link on the thank-you page and by email — click it, choose "Open Streamless," and you're done. You can also paste the key (or the whole activation link) into Settings › License.
Privacy
Streamless has no accounts, no telemetry, and no servers holding your data. The app talks to the network for exactly three things: looking up CD and album metadata (MusicBrainz / Cover Art Archive), checking for app updates, and activating a license. Your music and your listening habits never leave your Mac. Full details in the privacy policy.
Troubleshooting
Apple Music opens every time I insert a CD. That's macOS, not Streamless — and it's switchable. See the tip in the Ripping CDs section above: System Settings › CDs & DVDs › "When you insert a music CD" › Ignore (or Open other application… › Streamless).
My iPod doesn't show up. Check that it mounts in Finder first (classic iPods need to be in disk mode, which is the default). Try another cable or port — aging iPod cables are the most common culprit. If it's a Nano 6G/7G or iPod Touch, see the supported list above.
Tracks skip or won't play on an older iPod. Make sure you're on the latest Streamless (Streamless › Check for Updates…) and re-sync. If it persists, email us with the iPod model — we test on real hardware and want to know.
Some tracks didn't make it onto the iPod. The sync summary lists every skipped track and the reason — usually FLAC format or a source file that's gone missing.
Album art is missing. Give the background lookup a few minutes after a big import, or run File › Fetch Missing Album Art. Anything it can't find, drag an image onto the cover.
The app says files are missing. Your music moved, or its drive is unplugged. Reconnect the drive, or use the locate prompt to point Streamless at the new location.
Still stuck?
Email contact@streamless.app or reach us on Bluesky / Threads — see the support page. Bug reports from beta testers are gold; include your macOS version and iPod model if it's sync-related.