Google and Apple Have Been Screwing Around With Email Security and it Doesn’t Actually Help Security

TL;DR – Two-factor authentication (2FA) with Gmail, Apple’s native mail clients, and an email forwarding service is much harder to set up than it needs to be due to poor communication by both Google and Apple. The end result is that it’s just much easier, if people can’t sacrifice Gmail/Apple/Forwarding, to just turn off 2FA which is a bad thing.

I try to do the right thing. I turn on two-factor authentication on my Gmail account, don’t resuse passwords, etc. However, getting this up and running across all my Apple devices was a PITA and took a huge amount of googling and experimenting. Apple and Google’s history on mail, like just about everything, has been a clash of tech egos and insanity. I went through periods of turning 2FA on and off to get things to work correctly, and I can only imagine a non-technical user to just say, “fuck it” and keep it off. So despite Apple and especially Google’s preachings, their bickering and hair-pulling business decisions have helped no one but hackers.

In the old days, websites would just require a password to sign in. Two-factor authentication became popular to secure sites more important sites. Two-factor authentication is the process where a site or company requires a second way to verify you are trying to sign in besides just a password. Banks typically do this. If you are signing in on a new computer or browser, they often will send you a code in a text message on your phone, and you have to enter that code in the browser before they’ll let you in. The idea is that it’s harder to compromise both your password and your physical phone instead of just the former.

Google is Mostly to Blame

Instead of a simple text message, though, Google requires you to authenticate via the Google App. You have to download their Google App on the phone, and when you sign in elsewhere, the verification is done in that app. You have to click “Yes, I am trying to sign in on the desktop” in the Google App. There are also scenarios where they also text you a code to enter somewhere in addition to the app.

This is all fine and dandy, and makes it slightly harder to do an attack called SIM Swapping, but there are plenty of scenarios where you aren’t signing in via a browser. For example, an email application. I also have security cameras that are controlled by the camera maker’s app. I have to enter in a user name/password like the old days to email me when motion is detected. For those scenarios, Google introduced two methods – a setting called “Allow Less Secure Apps” and “App Passwords.” The former allows your username/password to be used anywhere in an old school way, and the later is available when you have two-factor authentication enabled. App Passwords generate one random password per application and ties it to a device, basically forbidding you to reuse passwords. So if someone breaks into my camera system, they can’t use that password to sign in on a Windows XP machine in Russia.

The problem is that Google, like usual, does a crappy job at communicating/educating the layman about these changes. Further, again, like typical Google, you can’t ever trust how long they will keep supporting a method or product.

For both “Allow Less Secure Apps” and “App Passwords,” they freakin’ warn you all over, that this is unsecure and you shouldn’t use it. That’s definitely true for Allow Less Secure, and technically true for App Passwords, but come on. App Passwords is essential for those scenarios without a browser and is actually a pretty good security mechanism.

Now you’re in a situation where App Passwords are perceived to be dangerous, and because Google warns you that it’s a bad way of doing, they imply they may yank them in the future. So you don’t use them. However, you still have to set up the security camera to email you when a rabbit is running across your driveway. How do you get that working? Turn off 2FA and turn on “Allow Less Secure Apps.” Congratulations, you are now no longer following best security practices. Despite what Google wants you to do, their communication compels otherwise.

Apple is Also Mostly to Blame

I fully admit a lot of Apple’s blame is because of my special snowflake setup. In the email specs and most apps including the Gmail web interface, you can choose a specific “Reply-To” address that is entirely different than the email address on the system. I use this feature. I use Gmail, but I never give out my Gmail address. The Reply-To address is my alumni address. I send out email through Google, and recipients’ email clients are supposed to use the Reply-To address. They don’t always and instead respond to my Gmail address. It works, but my Gmail address is not my “real” address. My school alumni address forwards to the Gmail account.

In my encounters, this is an uncommon requirement, but I’ve met many people, and organizations, where this setup is used for various reasons. It isn’t exactly a rare edge case.

Apple’s Mail applications has been inconsistent and slow at incorporating Google’s security changes for both macOS and iOS. The smoothest way for native applications to support 2FA is to launch a browser window, kick you over to Google, make you sign in with Google, Google then says yea or nay, the browser then tells the OS yea or nay. *Hand Waves* this is a type of 2FA called Oauth.

It’s Been Inconsistent on macOS

There are two ways you can add a Gmail account to macOS You can choose “Gmail” which does a lot of under the hood magic, or you can directly enter Gmail server settings via “Add Other Account…” I hated the “Gmail” method. It never allowed you to change your Reply-To address and hid what the hell was going on. For years up to and including Mojave, I had to use the later to accomodate my special snowflake email forwarding setup. It worked ok until 2FA was turned on. When you added an account via “Gmail,” it at least supported the Oauth flow to work. If you add it via “Add Other Account…” it doesn’t. So it looked like you were dead in the water with 2FA, Gmail, and a forwarding email.

However, you actually weren’t dead in the water because you could set up an App Password. The problem was usually didn’t tell you what was going on. It just spun and spun until time out and just says “ is not responding.” Occasionally a dialog box pops up telling you to use App Passwords, and that’s how I discovered that was the issue. I set up an App Password, an lo and behold, it works. Now, this specific issue could have been 100% Google’s fault. Maybe they didn’t provide a usable error for to report. Who knows.

Giving Apple credit, they did indirectly fix things in Catalina. If you add an email via the “Gmail” method, it now allows you to change your Reply-To email address. So you’re kicked into the Oauth flow and can use an email forwarder. As far as I know, though, “Add Other Account…” still doesn’t support Oauth.

It’s Been a Consistent Dumpster Fire on iOS

iOS is a different story. Setting up a gmail account as “Gmail,” does not allow you to change your email address in outgoing emails at all. This is true even up to iOS 14 released a few days ago, so that is not an option. Setting up the server directly, never gives you the App Password warning. It just spins, timesout, and says something like “ is not currently available.” So if you only use email on your phone, you’ll never be told to use an App Password. Again, still the same as of iOS 14.

I can’t imagine how you would figure this out if you didn’t have macOS or if your Google skills weren’t exemplary. If you use a Reply-To, it is just be easier to turn off 2FA and set up Gmail as a regular IMAP server. You are led to believe that 2FA, iOS, and email forwarders are an impossible combination.

Other Apps: Yay!

All this mess made me explore other email clients. The thing they all have in common is that they do not try to be clever and hide things, and allowed you to change your Reply-To address.

Edison on iOS was great until it wasn’t. Hopefully an issue like that won’t pop up again.

Thunderbird is a throwback that is usable, but the interface is woefully outdated for modern wide screens and laptops.

Yeah, I actually used Outlook for a while on my 2015 MBP (the last great Macbook Pro) on Mojave. It ain’t terrible.

In Conclusion, This is What You Need to Do…

With a lot of finagling, you can actually use two-factor authentication and special email setups with Apple software. On macOS, in < Catalina, use an App Password via server settings directly. In Catalina and hopefully beyond, add the account as a Gmail account. In any version of iOS, use App Passwords instead of your normal Gmail password. You will never know this strictly from using iOS.

It would be a lot easier if Google wasn’t constantly changing Gmail security up, and Apple stopped trying to be so damn clever with their email clients. Both companies need to stop trying to force people into screen time on their ecosystems at the expense of good security.

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