Mac File Sharing

When it comes to sharing data from a Mac, there are plenty of scenarios and plenty of methods. Identifying the right tool for the job comes with experience. Whatever method you land on today might not be the best method in a year–and that’s OK. Sometimes a system you already know how to use and troubleshoot is better than something new and unproven, no matter how many bells and whistles it has. And then there’s the gradual enshittification of tech, where the useful and free tool you once loved slowly becomes expensive and exploitative.

Regardless of circumstances, the criteria most people use to judge these tools in today’s tech world are security, speed, and reliability.

My Use Cases

There isn’t a one-size-fits-all solution for sharing files.

• It depends on the type of data you want to share: an image, a link, a single document, a 20 MB DMG, or an 11 GB MKV video.
• The type of device the intended recipient is using.
• The sensitivity of the information. There’s a big difference between a funny meme and a copy of your tax returns.
• How soon the information needs to be available to the recipient.

Scenario 1 – I have a link or image and I want to share it RIGHT NOW to the iPhone, iPad, Windows laptop, or MacBook my partner is using.

If you’re going from one Apple device to another, built-in tools like AirDrop, Messages, or email are all viable options, with AirDrop being the flakiest. That’s usually because both sender and recipient need the correct settings, and the recipient has to be savvy enough to know where the received file ended up on their device.

If you’re sharing with a Windows or Android user, a cross-platform messaging service like Signal or Telegram can work. For the tech-savvy, LocalSend is a useful app that’s cross-platform, free, and powerful, with a few gotchas. It has to be running on both devices, and anyone with a complicated firewall setup may be in for a headache.

Scenario 2 – I have several documents I want to share with my partner, who will need to download and use them on her MacBook.

When you’re at home, there’s no need to send the information through the internet. LocalSend is a good option. You can transfer files even if your internet connection is down.

While it’s relatively easy to turn on local file sharing for Macs on the same network, it’s a best practice to leave that turned off, as it opens up another attack vector for bad actors. If you resort to email, get in the habit of sending files in password-protected ZIP archives. Free tools like Keka can handle that easily. Another easy-to-use and powerful encryption tool is Encrypto.

If it better suits your purpose, most cloud services (iCloud, Dropbox, Google Drive) have Finder integration that lets you share links to files. Just make sure you know whether you’re sharing a copy of a file or sharing access to the file–there is a difference.

I don’t use US-based cloud storage for most of my files. The two services I do use, Koofr and kDrive, both offer sharing through links. Koofr offers lifetime access to 1 TB of storage for $139. kDrive has a 3 TB subscription plan for just €4.99 a month.

Scenario 3 – I have a collection of documents, images, and links I want to access from my phone, iPad, and Mac, with changes made on one reflecting on the others.

This is where you need a reliable cloud service. iCloud is built in, but results can vary wildly for all sorts of reasons. Sometimes I have folders on two Macs that live about three feet apart, and they’ll go days without syncing Desktop and Documents.

If you’re tech-savvy, there are self-hosted options like Immich for photos and Nextcloud, a roll-your-own cloud service with many compatible apps and plugins–but did I mention that it’s slow?

Scenario 4 – I have 16,000 books, 150,000 photos, and 32,000 songs I want to continually sync between four computers on the same LAN for reasons that make sense to me.

For giant jobs like this, the champ is Syncthing. The situation I describe above is my real-world use case. I like to manage my images on my relatively fast MacBook, but I sync copies to two ancient iMacs (running Linux) that I use as giant digital photo frames, while also maintaining multiple backups of my photos.

I also manage my ebook collection on my Mac, while syncing it to my self-hosted server so I can use Calibre Weband Audiobookshelf for remote access.

Scenario 5 – I am traveling and need to get files onto the hard drive of my home computer so I can remote in and do X to those files.

If your cloud service of choice isn’t an option–because it’s acting flaky, you have space limitations, or for other reasons–using Blip is worth considering. Blip is a free service that can handle large, multi-GB files and resume transfers if they’re interrupted. It uses TLS 1.3 for in-transit security.

It’s not pure peer-to-peer; your data uses Blip’s infrastructure for signaling. I sometimes have problems getting my devices, all signed into the same account, to see each other. Unlike LocalSend, Blip works across the internet, and plenty of people use it without issues.

My other suggestion in this category is Taildrop, the file-sharing protocol between your personal computers on the same Tailscale network. It’s as easy as using the share menu on your Mac or mobile device. It’s relatively new and still in alpha, but it’s free, and I’ve never had an issue with it.

Scenario 6 – I need to share a large file with a random internet stranger I may never talk to again.

This is a case where using a shared link from a cloud service or Nextcloud is your best bet. There are also browser-based sharing services that might work. PairDrop works well as a PWA in Safari.

Scenario 7 – I have a collection of files I want to share with the internet at large and be able to update and change them.

There’s no need to buy a domain name or open an account with a hosting service and CDN. Just use GitHub.

I’m no coder, but I’ve had a GitHub account for ages for several different reasons. It’s what I use to share my automation settings for Keyboard Maestro, Hazel, and Better Touch Tool. Using GitHub Desktop, I can move files into a folder on my Mac and sync them to GitHub in just a couple of minutes.

You don’t have to understand pull, push, or git to make use of GitHub. Once you have an account, you can also use it as a free backup service for Obsidian or even blogging platforms like Micro.blog.

A Couple of Newcomers

If you’re interested in these kinds of apps, there are a couple of new ones worth keeping an eye on.

Zynk – a new freemium service worth testing.

• Send folders, photos, and multi-gig archives
• Works across phones, laptops, TVs, and servers
• End-to-end encrypted
• Resumable transfers
• No size limits
• Built-in chat and voice
• Share via the app or browser links
• Preview files in the app before downloading

Droplet – still in TestFlight. I’ll be writing more about this when it’s released. Droplet is an app for almost instantly moving files between Macs and iOS devices. It offers a simple drag-and-drop interface that literally takes about 15 seconds to learn.