Share files securely

Imagine you’re staring at a file or folder—perhaps confidential employee information that you need to send to your accountant. If attaching it to an email message makes you think, “That doesn’t seem like a good idea,” award yourself a gold star! 

Sending sensitive files via email is a bad idea, partly because the email could be intercepted in transit, but more because the files then live in both your and your recipient’s email accounts in an unprotected form. If an attacker were to gain access to either of your email accounts, they might scan for patterns like credit card numbers, ID numbers, phone numbers, and postal addresses and find them even in attachments.

There are ways of encrypting email messages so they can be read only by the recipient and never exist in an unencrypted form other than while being created or read, but they’re difficult to set up and fussy to use. For most people, most of the time, encrypted email is overkill. 

For a more straightforward solution to exchanging information securely via email, use password-protected and encrypted ZIP archives. They’re easy to create on the Mac, either using a simple command in Terminal or with a third-party utility. And better yet, any Mac user can expand them using the built-in Archive Utility simply by double-clicking and entering the necessary password.

Create Encrypted ZIP Archive Using Terminal
Although many Mac users are intimidated by using the Unix command line in Terminal, making an encrypted ZIP archive is easy enough for anyone. All it takes is typing a single command, dragging a file or folder to Terminal, and entering a password twice. Follow these steps, which make an encrypted ZIP archive on your Desktop:

1. In your Applications folder, open the Utilities folder and double-click Terminal to launch it.
2. Type (or copy and paste) this command, replacing “archiveName” with whatever you want to name the ZIP file and making sure to type a space after the last letter—the “p” in “zip”. (The tilde ~ character is Shift-backtick, and it’s the key to the left of the numeral 1 key.)
   
   zip -er ~/Desktop/archiveName.zip
    
3. Drag the file or folder you want to protect into the Terminal window to complete the command.
4. Press Return, and when prompted, enter the desired password twice—the second time is for confirmation.

1. Launch Archiver.
2. Drag a file or folder to the Archiver window and click the Archive button in the toolbar.
3. Select the archive format (use ZIP), click the Encrypt checkbox, enter the password twice, and click the Archive button in the toolbar.
4. Drag the ZIP archive to the Desktop or another folder and click the Done button.

Instead, use what’s called an “out of band” communication channel. In other words, if you’re going to send the ZIP archive via email, communicate the password in a phone call or text message. That would keep the password safe if either of your email accounts were compromised.

If you’re sending password-protected ZIP archives to a particular person regularly (and the files don’t contain state or corporate secrets), you could agree on a system for generating passwords so you don’t have to communicate each one individually. For instance, you could combine a random word and the current month, so the password would be “cheddar9September” one month and “cheddar10October” the next.

As you can see, you can use this technique with so little extra effort that it’s worth ensuring a higher level of security whenever you need to share confidential information.
 

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Software Recommendations

Hardware Recommendations

• MacBook (Early 2015 or later)
• MacBook Air (Mid-2012 or later)
• MacBook Pro (Mid-2012 or later)
  • Note that 2016-2019 MacBook Pro models have a higher than usual keyboard failure rate. Used 2015 models, which use a different style keyboard, may be a more reliable option. The new 2019 MacBook Pro 16" model uses a new keyboard mechanism and should be fine.
• Mac mini (Late 2012 or later)
• iMac (Late 2012 or later)
• iMac Pro (all models)
• Mac Pro (Late 2013 or newer)

• iPhone 6S or newer. Older iPhones cannot run iOS 14. 
  • iPhone 7 models have a higher than normal failure rate over time. Given the choice, we would recommend iPhone SE (2020) model as a strong alternative to iPhone 7 models. 
• iPad Air 2 or newer
• iPad mini 4 or newer
• iPad Pro (all models)
• iPad 5th generation or newer

• Apple Watch Series 4, 5, or 6 or SE highly recommended.
• All versions (Series 0 through Series 6 and SE) are secure and acceptable though Apple Watch Series 0, 1, and 2 will not run the latest version of WatchOS and therefore lack both the speed and features of later Apple Watches.  

• Apple TV 4K is recommended. Apple TV HD (4th generation) is fine as well.
• The latest version of the AppleTV Remote is available for stand-alone purchase ($59). It works with Apple TV 4k (1st and 2nd generations) and Apple TV HD. It's a lot better than previous remotes. 
• Older models of Apple TV do not support tvOS and cannot run Apple TV Store apps, though we are unaware of any major security issues.