How to Send Encrypted Files (by Email, Airdrop or iMessage on Mac)

Send encrypted files from your Mac to anyone, on any device, using a FREE app called Keka. Using Keka the recipient of your encrypted files won’t need to install any software, they just need the password used to encrypt the files.
0:00 - how to use Keka
3:09 - send via iMessage
3:32 - send via Airdrop
3:51 - send via email

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Transcript:
Keka is a free app that encrypts your files and zips them up into a single compressed folder, making them easy to send and reduces the overall file size in the process.

If you google Keka, it should be the first result that pops up. Now when you open the website you’ll likely be drawn to the App Store link. I would recommend ignoring this link because the app is not free on the App Store. You have to pay for it. However, if you go back to the website, there is a link just below this which lets you download a free version. I’m not entirely sure of the difference between the paid and free version, I suspect there might not be any, but this free version is perfect for our needs.

Having installed the app in the usual way, when you open it you’ll see this screen.  There are a few options here, but essentially you just want to add a password. This will be the password the recipient will use to decrypt and view the files you are sending them. Having added a password I recommend ticking this box which will ensure your files are encrypted using a strong level of encryption.

Having done this, it’s then just a matter of dragging and dropping your files over the app. I’ll be sending this text file but you can send literally anything, within a reasonable size limit. You’ll immediately see this warning which appears because we ticked the box to use 256 AES encryption. The message is basically telling us that some Mac and PCs might have trouble opening the file using this stronger encryption. This is not the case for Apple Silicon Macs running the latest versions of MacOS, or iPhones and iPads, which can all decrypt the files just fine. However, it is true of Windows PCs  so if you think the person receiving the file might be using a Windows PC or an old Mac, you might want to choose the option to use legacy encryption. Your file will still be encrypted using a password but it will just be using a weaker cipher.

You’ll be prompted to save your new encrypted Zip file and give it a name. By default it’ll save to the same directory as the original files. At this point you're all done with Keka, you can close the app, and send your files by whatever means suits you best. I’ll be sending my files in 3 different ways to show you what happens on the other end, and I’ll start by using iMessage to send the file to Wilson. When Wilson receives the file he just needs to save it to his computer and double click the file to open it. He’s prompted for the password and, having entered the password, there’s the decrypted file. Easy peasy.

Now let's see what happens when we receive the file on an iPhone. Just for something different, this time I’ll send the file using Airdrop. Wilson just needs to accept receipt of the file and save it to his Files app. Tapping on the file, he’s prompted for the password, and again there’s our decrypted file.  

Finally I’ll send the file to a Windows PC as an email attachment. It’s worth remembering that whilst the attachment is encrypted, the actual email is not, so don’t be tempted to include the password in the contents of the email. An encrypted chat messaging app like WhatsApp or Signal is a better option for sending your password. Having received the file, Gmail quite correctly warns Wilson that downloading a random zip file from an email is very risky. However, since I sent it, we know it’s fine so we’ll continue. Now, as I mentioned earlier,  because I ticked the box to use strong encryption, unlike Mac, Windows cannot natively decrypt the file. It just displays a very unhelpful error. So, if you are sending your encrypted file to a Windows PC, you can either zip the file in Keka using legacy encryption or the PC user will need to install an application such as 7zip, which is able to decrypt the file just fine.

Attribution: Freepik and others on www.flaticon.com