Picking up Gmail with Apple Mail

TidBITS Talk
1

Sonoma 14.3.1

I changed my Google password. MacOS Mail pops up a window saying “Enter the password for the account xxxxxx” and provides two buttons Cancel and Open Browser. I click Open Browser and am taken to a special web page that asks me to sign in with the new password. I fill in the account name/email, then the password, then the 2FA number I receive and click next. The web page provides buttons to cancel or sign in to MacOS. I click sign in to MacOS and get the following:

400. That’s an error.

The server cannot process the request because it is malformed. It should not be retried. That’s all we know.

Ignoring the ‘It should not be retried’ I retried this multiple times with same result.

I tried creating a new account through MacOS > System Settings > Internet Accounts but it ends up following the same sequence.

I can sign in to the Google account at mail.google.com.

I have successfully followed the prompts to update the password on iOS but MacOS Mail can neither pick up nor send using that email address.

Can’t find any Help in Google Help. (Surprise!)

Wondering if anyone here has suggestions.

2

I had a similar problem recently. In my case, it seemed to be caused by macOS Safari. I temporarily changed my default browser to Chrome (I keep a copy of Chrome on my Mac for troubleshooting situations like this) and retried the macOS/Apple Mail login sequence. I was able to login successfully.

My iOS and iPadOS devices did not have the same login problem. That was what led me to try Chrome for the macOS login.

3

Thanks for the tip. I tried changing default to Chrome but the Mail link opened Safari anyway which then asked if I wanted to make Safari my default!

4

It’s been a long time since I changed a Google password, so I haven’t seen this. But if this was me, I would delete the account and set it up again.

5

I tried to set up a new account in MacOS > System Settings (new name same account) but the process requires following the same web page link to authenticate and it fails the same way.

6

I think I’d try creating a new user account on the Mac and try to set up the account there to see if it’s something with just your account, or affects any account on the machine.

I know that I just set up an a Gmail account on Sonoma 14.3 for the first time yesterday on a Mac mini and it set up just fine. I haven’t had a chance to update that machine to 14.3.1 yet.

7

Perhaps my problem had a different cause. In any case, here are the steps I followed:

  1. Quit Apple Mail
  2. Quit Safari
  3. Open Chrome
  4. Set Chrome as the default browser (Chrome > Settings > Default Browser)
  5. Quit Chrome
  6. Open Apple Mail
  7. Enable Gmail account (Apple Mail > Settings > Accounts)
  8. Complete Google login sequence

Alternatively, I’ve also triggered the Google login sequence at System Settings > Internet Accounts (I’m on Ventura) by toggling Mail off and on in the past.

8

Problem solved.

As noted above, even after setting Chrome as the default, the authentication sequence opened Safari, which wasn’t running, and failed in the same manner.

However, I then switched the default to Brave, closed all other browsers and tried again, and this time the process completed as expected.

So, is this a Safari issue? Pure speculation on my part but could it have something to do with Safari’s security/private browsing settings?

1 Like
9

I see that you have found a solution. If I had been here earlier, I would have suggested copying the URL from the Safari address bar and pasting it into Chrome (or some other browser). Does anyone know if that would have worked?

10

I’ve used apple mail to pick up gmail everyday ever since Eudora faded away. I’ve always used only Firefox to access gmail with browser and from time to time access with Firefox to update- change password or set spam etc. Never had a similar problem. Never really used Chrome

11

In my earlier posts, I chose Chrome for authorizing macOS and Apple Mail to access Gmail because I wanted maximum compatibility (use a Google browser to manage a Google online service).

But troubleshooting a login problem isn’t limited to a temporary switch to Chrome. It is equally valid to try any non-WebKit based browser, including Microsoft Edge, Brave, and Firefox. One browser that might not be so great for figuring out problems with Safari, though, is DuckDuckGo because it uses the same Apple rendering engine (WebKit) as Safari.

12

Interesting. I use Brave by default but its security features prevent a few sites from running as desired. In those cases I switch to Safari and usually have no problem. Just shows how useful it is to have multiple browsers, with different technology bases, available.

13

I think you need an application password to provide to Mail

14

Good to know that changing the Google password might cause Apple Mail problems, and that there are solutions such as using alternative browsers.
I use Safari as my default browser under Sonoma but have Microsoft Edge as a backup. I needed this yesterday when managing a web-hosting account (adding SSL to my web pages). It wouldn’t process correctly with Safari.