I’m trying to figure out the smoothest way to hook it up to my MacBook.
I’ve seen a few different approaches mentioned online: some people just plug it in and expect Finder or a native app to pick it up, others use general Android file-transfer tools like Android File Transfer or MacDroid since the watch shows up as a USB storage device. I’m not sure which route is actually the most convenient and reliable in practice.
For normal syncing and updates, Garmin Express is probably the simplest option. It’s Garmin’s official desktop app, so you just install it on your Mac, connect the watch over USB, and let it sync activities with Garmin Connect. It also handles software updates, music, and Connect IQ apps. In my experience, it’s been the most reliable method.
Generic file-transfer apps aren’t really a replacement for Garmin Express. They may let you browse the watch’s storage, but they won’t necessarily handle workouts, FIT files, and account syncing the way Garmin’s software does.
Android File Transfer isn’t an option anymore since Google discontinued it and removed the download. If you only want Finder-style access to the files on the watch, MacDroid is one of the replacements people commonly suggest. It can mount a compatible device as a drive over USB or Wi-Fi.
If Garmin Express gives you trouble, you still have a couple of fallback options:
A charging-only cable or flaky USB-C hub can make this look like a software problem. Use Garmin’s data cable directly into the MacBook, unlock the watch, and open Garmin Express. MacDroid isn’t needed for syncing, and the watch may not appear in Finder even when Express detects it.
If the watch appears under the Mac’s USB hardware list but not in Garmin Express, you have a permissions or watch-mode problem. If it does not appear there at all, suspect the cable, adapter, port, or dirty charging contacts.
On the watch, hold UP and go to System > USB Mode. Select the data-transfer option, usually Mass Storage rather than Garmin mode. Garmin mode can charge the watch without exposing it for normal file transfer. The exact wording can vary slightly with software versions.
Then check the Mac side. Open System Settings > Privacy & Security > Files and Folders, expand Garmin Express, and enable Removable Volumes. Apple silicon MacBooks may display a separate prompt asking whether to allow the USB accessory. That prompt is easy to dismiss without realizing it, and Express will keep acting as though nothing is connected afterward. Quit and reopen Express after changing the permission, or restart the Mac if it still does not detect the watch.
A useful test is Apple menu > System Information > USB. Connect and disconnect the watch while watching that list. If the entry changes, macOS sees the hardware and replacing apps or cables probably will not fix the underlying issue. If nothing changes, connect the Garmin data cable directly to the MacBook, clean the four contacts on the back of the watch, and avoid a monitor, dock, or hub for the test.
I would leave MacDroid closed while troubleshooting. It is not required for updates or Garmin Connect syncing, and having another program trying to access the device can complicate detection. The Forerunner 265 may not behave like a regular Finder drive anyway, so Finder visibility is a poor test. Once Express recognizes it, use Express for firmware, music management, and account setup. For routine activity uploads, the Garmin Connect phone app is usually less effort than plugging the watch into the Mac every time.
Don’t factory-reset the watch just because Garmin Express cannot see it. A reset usually won’t fix a USB connection problem and creates more setup work.
The correct desktop setup is Garmin’s proprietary four-pin charging/data cable connected directly to the MacBook, then Garmin Express. Current cables use USB-C at the computer end. If yours uses USB-A, the adapter must support data, not only charging. MacDroid is unnecessary for Garmin syncing and should stay closed while troubleshooting.
Unlock the MacBook before connecting the watch and accept any “Allow accessory to connect” prompt. On the watch, hold UP, open System > USB Mode, and select Mass Storage rather than Garmin mode. Then launch Garmin Express. Charging alone proves very little because an Apple silicon Mac can supply power while blocking data access.
@kevinthesignal is right that Finder is a weak pass-or-fail test. Check Apple menu > System Information > USB instead. If the Garmin entry appears there, concentrate on Garmin Express permissions or reinstalling Express. If the USB list does not change at all, try another genuine data cable, clean the watch contacts, and bypass every dock, monitor, and hub.
If your actual goal is activity syncing and firmware updates, you may not need the Mac connection. Pair the 265 with Garmin Connect on your phone and configure Wi-Fi. The watch can upload activities and receive software updates through Bluetooth or Wi-Fi, leaving USB mainly for Express-specific tasks and locally managed content.
If you’re on a recent macOS with a fairly current firmware on the 265, the whole USB question mostly goes away. Garmin dropped the old Mass Storage behavior on newer Forerunners, so the watch shows up as an MTP-style device instead of a plain drive, which is exactly why Finder looks empty and why the USB Mode menu might not even offer the option some people expect.
That’s also where I’d gently push back on the MacDroid angle. It’s built for Android over MTP, and a Garmin isn’t a phone, so I wouldn’t count on it seeing the watch at all. Fine to close it while you test, like @omegahive5590lab said, but I wouldn’t treat it as a real fallback for this device.
Honestly, if your goal is syncing and updates, skip the cable drama. Pair with Garmin Connect on your phone and let it pull firmware over Wi-Fi. The Mac connection is really only worth fighting for music or Connect IQ stuff.
Syncing activities and browsing the watch like an external drive are two different cases, and the Forerunner 265 is much better at the first. For routine use, let Garmin Connect on the phone handle uploads. If you specifically need a Mac connection, use Garmin Express and don’t treat Finder visibility as the goal.
A detail that can complicate this on work or school MacBooks is device-management software. Even when macOS sees the Garmin under System Information, company security policies can block removable devices or prevent Garmin Express from getting access. No cable, USB mode, or third-party MTP app will fix that. Testing from an unmanaged Mac or asking IT about USB accessory restrictions can save a lot of pointless troubleshooting.
For an occasional FIT file, syncing through the phone and downloading it from Garmin Connect in the Mac browser is usually cleaner than trying to browse the watch directly. I’d only spend time fixing USB access if you need a desktop-only task or the watch cannot sync wirelessly.
Making the Mac your main sync method adds friction for no real benefit. For everyday activities, pair the 265 with Garmin Connect on your phone and enable Wi-Fi. Connect IQ installs can be handled from the phone too, so USB is not required for that.
When you genuinely need the Mac, use Garmin Express with a known data-capable cable plugged directly into the MacBook. Ignore Finder and skip MacDroid. Finder-style browsing is not a reliable expectation with this watch. Use Express for desktop music transfers or recovery work, then go back to wireless syncing.
Expect USB on the 265 to behave like an app-specific connection, not a normal external drive. Use phone syncing for everyday workouts; only troubleshoot Garmin Express and the data cable if you need a desktop-only task, since Finder visibility proves very little.
Don’t spend money on a third-party manager for this. MacDroid keeps getting linked here, but it’s an Android device manager, and a Forerunner isn’t an Android phone. @zerodev5513net already flagged that, and I’d take it a step further: paying for a tool that probably won’t even mount the watch is just wasted effort. Close it and forget it exists.
The bit that’s genuinely worth keeping from earlier is the phone-first workflow. If all you want is your runs on the Mac, sync to Garmin Connect over Bluetooth, then grab the file from the web dashboard. You can pull the original FIT out of Connect, not just a GPX, so you’re not losing anything by skipping the cable.
Cable only matters for music, Connect IQ, or a stuck firmware update. For everything else the USB rabbit hole isn’t worth your afternoon.
Don’t unplug the watch while Garmin Express is updating firmware or copying music, even if it looks idle. For the smoothest setup, use Garmin Connect wirelessly day to day and reserve the Mac cable for Express-specific jobs.