I’m having trouble connecting my Kindle to my Macbook through a USB cable. My Mac doesn’t seem to recognize the device, and I need to transfer some books and documents. I’ve tried different cables but nothing happens. Has anyone else had this issue or know what I can do to fix it?
I literally spent an hour staring at my Mac and Kindle and thinking how to connect my Kindle to my Mac using USB. If this has ever happened to you, you know it feels like tech gaslighting: “Oh, is it my USB port? Is it my cable? Does my Kindle just hate Macs?” Turns out, it was my fault—I was grabbing some old USB cable from my kitchen junk drawer. The only thing that cable charged reliably was my frustration. 
But then I noticed the cable the Kindle actually came with, and—bam!—my Mac instantly recognized it. Apparently, not all micro USB cables are created equal. It’s like trying to charge your Tesla with a garden hose.
Fun fact: Every time I think I’ve solved a problem on my Mac, something else pops up. Lately I needed to pull files from a couple of Android phones (long story, family group chat drama). But using just a cable doesn’t usually cut it.
A while back, I ran Android File Transfer with no sweat. But with my shiny new Mac upgrade, poof—no way to re-download it, looks like it’s gone for good!
Anyway, some quick poking around, and I stumbled upon MacDroid. It’s actually pretty slick, kind of a worthy replacement for the increasingly irrelevant SendtoKindle thing. Works with all the Amazon gadgets I have—be it the Paperwhite or the snazzier Colorsoft Signature.
Quick Start
- Install the app from the App Store or their official page.
- Plug your Kindle into your Mac—but follow the steps MacDroid gives you to get it hooked up as an Android device.
- Congrats—just drag ’n’ drop your files, no magic incantations needed.
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Honestly, I’m not here to tell you it’s going to change your life. But out of the maybe five or six apps I tried—some crashed, some wanted money upfront, some looked like abandoned science projects—MacDroid just worked. Files, copied. Kindle, happy. My sanity, restored (sort of).
Super intuitive—no cryptic error codes, no twelve-step setups. If you’re the type moving files a lot, having a tool that doesn’t flake out is key.
If you run into any weirdness, drop a question—I’ve probably googled it already.
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Well, Mac + Kindle USB issues, aka “the cursed handshake” (seriously, half my hair’s gone from yanking at this). I saw @mikeappsreviewer vouch heavy for cable selection and the MacDroid app route—and to be fair, sometimes that’s clutch. But, not gonna lie, I’ve had Kindles still play dead even with the blessed original cable and all the drivers in the world. It’s like they’re stubborn on principle.
Before giving another app a go, have you checked what “USB mode” your Kindle’s in? (Some models these days default to charging only—makes me wanna throw mine out the window, tbh.) When you plug in, your Kindle should show a prompt for “Charge” vs “File transfer mode” or “USB drive.” Annoyingly, sometimes it never offers—toggle it by unlocking, then replugging the cable a few times. Or try a full restart of both Mac and Kindle (old-school, but weirdly helps sometimes).
If Finder doesn’t see the device and it’s not showing on Disk Utility, don’t rule out Mac’s own security stuff—System Settings > Privacy & Security > Files and Folders. Sometimes the Mac’s like, “Nope, I choose violence.”
And yeah, MacDroid is actually not just a shill option: it finesses Android file transfer for you (Kindle’s basically Android under the hood), and that can break the stubborn silence between devices. But personally, I still do a send-to-Kindle email or use the Kindle app for things like PDFs if it’s not time sensitive, just so I’m not depending on the USB lottery.
One more random fail-safe (learnt it the hard way): try connecting in Safe Mode on your Mac. Sometimes background processes freak out the USB connection—no joke.
So, to summarize: cable matters, check Kindle prompt, reboot everything, scan security/privacy, THEN go for MacDroid if it’s still being a brick. And if all else fails, scream internally and use the cloud. You’re not alone—it’s not just you!
Alright, first things first—@mikeappsreviewer and @yozora are on the money about cables being shadier than a sock drawer, but honestly, sometimes it’s not even the cable’s fault. I’ll bite: not all USB ports on the Mac are created equal either. One of mine literally refuses to talk to anything except my mouse. So if you haven’t already, try moving your cable to a different port—even the USB-C adapter thingies (which, ugh, dongle life) can have different behaviors depending on how your Mac’s feeling that day.
Something folks barely mention: open Finder and hit Shift+Command+U to pop open the Utilities folder, then launch Disk Utility—sometimes the Kindle is chilling there as an unnamed mass storage volume, waiting for you to mount it. If you see it there, manually mount it and boom, files.
But here’s where I gotta throw a curveball: I’m not huge on external apps unless I absolutely have to, but MacDroid actually earns its keep. Fact is, half the time Amazon “updates” something and the Finder connection breaks for random weeks until someone at Apple or Amazon fixes it. MacDroid’s like the translator in the room when two people are arguing in different languages—it just cuts the bickering.
Curious thing—have you checked if your Kindle’s too old or too new? Ancient Kindles = no drivers for current MacOS. Brand new ones = experimental USB protocols, so lol, good luck unless they feel charitable with firmware updates. (Cloud isn’t always the enemy if you’re stuck.)
Also, and I know this’ll sound like tech superstition, but leave your Kindle on the homescreen (not in sleep or on a book page) before plugging it in. I once fixed my “invisible Kindle” problem that way: wake device, go home, plug, pray, repeat.
Worst comes to worst, skip the whole tangle and just email your documents to the built-in free Kindle address, let Amazon serve as your beleaguered middleman. Not ideal for big file dumps, but way less hair-pulling.
TL;DR: Rotate USB ports, check Disk Utility, use MacDroid (seriously, it just works, never thought I’d say it), fiddle with what screen your Kindle’s on, and don’t trust any cable that came free with random electronics. Anyone else run into the bizarre “device can’t be mounted” error and then it just fixed itself for no reason? Or is that just me?
If your Kindle and Mac snub each other harder than two exes at a wedding, here are moves beyond just cable swaps and port roulette—yeah, the previous tips on trying cables/ports and poking Disk Utility absolutely track, but let’s offer another perspective.
First up, sometimes your Mac just doesn’t want to speak, period—think “speechless” rather than “not listening.” Especially since macOS Sonoma, I’ve seen weird permission popups where the system quietly blocks new hardware mounting until you explicitly agree. So, after you physically connect Kindle, head to Finder > Locations for any pop-up. If nothing, launch System Settings > Privacy & Security > Files and Folders, look for Finder or MacDroid, and make sure access is allowed. (Random, but it’s fixed “invisible devices” more than once for me.)
Drive tools like MacDroid that the others mentioned are way more stable than trusting that Finder will always behave, especially if your Kindle isn’t super new or super old. MacDroid is plug-and-play-ish, no drivers, nice UI, supports loads of Android-type devices (yep, Kindle’s software counts here). Big pro: file transfer there rarely bugs out or stutters, and you avoid Finder’s cryptic errors.
Con: There’s a free version, but if you want two-way transfer, the paywall pops up after the trial, and, notably, it’s an extra thing running on your Mac. Some power users won’t like that. Also, it’s not as “baked in” as, say, Send to Kindle (which is a whole other drama if you’re moving non-DRM stuff).
VS some of the other approaches mentioned, MacDroid’s bonus is that it tends to survive through OS and Kindle firmware updates—Finder tricks break constantly with software changes, in my experience. However, for someone who wants pure simplicity and doesn’t care about speed or folders, just emailing files to your Kindle address (as was touched on) by others is still the zero-headache option.
Last random nugget: if MacDroid and all cables fail, check if the Kindle is locked with a passcode—the device must be unlocked and on Home. Also, on newer Macbooks, low-power “eco” USB ports can throttle power/data, so a direct plug into the main left-side port sometimes just…works.
TL;DR pros of MacDroid: stability, compatibility, slick UI, works under lots of weird failures; cons: price after trial, needs background process, not for folks who dislike third-party tools. Competitors like Android File Transfer or clunky web UIs exist, but I’d rather not gnash my teeth through those.
So, click around those Privacy/Settings, keep MacDroid as your backup quarterback, and keep cables at the ready—it’s a safari out there.