Resolved Apple Mail and Google's May 30 less secure sign-in deadline

[JohnSFO]

I've been getting emails from Google about a May 30 deadline on using 3rd party apps to access Gmail. I believe the Apple Mail app that I use on my iMac is the reason I'm getting the messages. I've done some extensive research online about how to resolve the issue, but the best solution I've found is deleting my accounts in Mail and signing up again using "Sign in with Google." But when deleting the accounts it states that I'll lose all of my data associated with the account. Surely there's an easier way to resolve this issue than dumping all of my emails and starting from scratch? Has anyone else been getting the May 30 deadline emails? And how have you dealt with it, specifically for Apple Mail accounts using POP and SMTP settings. Thanks.

 

[bradman83]

I've been getting emails from Google about a May 30 deadline on using 3rd party apps to access Gmail. I believe the Apple Mail app that I use on my iMac is the reason I'm getting the messages. I've done some extensive research online about how to resolve the issue, but the best solution I've found is deleting my accounts in Mail and signing up again using "Sign in with Google." But when deleting the accounts it states that I'll lose all of my data associated with the account. Surely there's an easier way to resolve this issue than dumping all of my emails and starting from scratch? Has anyone else been getting the May 30 deadline emails? And how have you dealt with it, specifically for Apple Mail accounts using POP and SMTP settings. Thanks.

Mail cache and POP mail would be stored in your ~/Library/Mail/ folder. You could make a copy of this folder and set aside prior to deleting and re-adding the account using the Sign in With Google option and then use the Import Mailboxes function to try to re-add the missing mail by pointing it to the copied .mbox folders.

 

[JohnSFO]

Thanks for your suggestion. I'm trying to figure out how to make it work though. I have 3 Gmail accounts, but I don't keep emails in the inboxes for very long. Emails either get deleted or moved to other folders. If I delete one of the accounts will the emails in the subfolders disappear as well? Because I use POP it deletes the emails on Google's server once I download them to my computer, so I want to be sure I'm not deleting anything that I can't get back. As a test I copied the inbox for one of my accounts, but when I looked at the size it was only a few KB suggesting that it wasn't including emails that I had moved to other folders. Also, when I go into the Library Mail folder there doesn't appear to be any proper .mboxes to copy. This whole thing with Google is so annoying and I wonder how many others will be dealing with it closer to the May 30th deadline (or when their Mail app no longer functions properly on June 1st!)

 

[AZhappyjack]

POP3 email is downloaded to the device where it is viewed. Based on the settings within that device, it can remain on the POP3 server for a period of time (typically a week or in some cases 30 days)... but you already have copy on your computer, and the odds are most of the email has been removed from the server (because you downloaded it). So there's no need to worry about losing that email... and since you've moved it to other folders, it will remain where you moved it.

You could simply remove the email accounts from Mac Mail and then re-add them using the Oauth2 dialog. This will "fix" the issue with insecure methods that the Google warning is all about.

 

[MacGizmo]

From Google's support page:

If an app uses less secure sign-in technology, you might not be able to use it with your Google Account.

You can sign in to your Google Account from any third-party app that has the "Sign in with Google" option. You can also sign in to your Google Account using all Google products, like Gmail.

I believe macOS uses this when creating your Gmail account in System Preferences.

 

[JohnSFO]

UPDATE: I went ahead and removed my lesser used Gmail account as a test, and as dwfaust suggested I did not lose emails that I had placed in other folders. The one side effect though is when I re-added the account it was set up as an IMAP account, without the option to create a POP account. It's my personal preference to use POP, to have emails delete from Google's servers and my iPhone once I've downloaded them locally to my iMac. I've researched it, but haven't found a way to create a POP account using Google's new security standards. Has anyone else run into this problem when adding a Gmail account to Mac Mail? Is there a workaround? Thank you to all who have helped so far.

 

[alcforest]

I would also like to know if there is a way to keep POP when updating to new Google requirements. For some of us POP is essential (need to keep confidential work email on my Mac and off my phone). Very grateful if anyone can suggest how to do this.

 

[Fishrrman]

OP:
"I've been getting emails from Google about a May 30 deadline on using 3rd party apps to access Gmail."

Does it happen to resemble this at all?
(Yes, I realize this is not "for google" -- but it's an example of an email scam):

 

[JohnSFO]

No, it's legitimate, but thanks for bringing up the idea of an email scam. I appreciate it. An online search shows that many people are getting the same email from Google and having to deal with making changes to their email clients before the May 30th deadline. It's only affecting people who created their account(s) without using the "Sign in with Google" process. I'm finding that deleting the account from Apple Mail and re-adding (and signing in with Google) solves the problem, but leaves me with an IMAP account instead of POP, but I might have to just get used to IMAP.

Here's what the email looks like:

 

[jasnw]

I’ve been seeing this message as well, and have been fiddling with work-arounds. I’m also needing POP-like behavior while interfacing with IMAP protocol connections. The current status of my kludge-around is to:

1. On the Gmail end of an IMAP account, set up a “filter” that automatically applies a “label” (analogous to copying to a folder named “label”) to all incoming mail to provide for an archive copy on the Google end. This effectively puts a copy of that email under "label".

2. In Mac Mail, set up a rule that moves all mail coming in from this Gmail account into a mail folder under “On My Mac” that serves as the Inbox for this account. This will delete the copy of the email in the Inbox on the Google end (keeping the archive copy you made) and put a copy of the email on your computer in the On My Mac inbox folder you’ve set up.

I’m doing this on an older Mac running El Cap, but this will probably work on newer versions of the OS. There may be a chance of action #2 stepping on action #1 with a result that no archive copy is saved on the Google end, but I’ve never run into a problem with that.

I suspect there may be some fancy way to set up an “On My Mac” folder directly under the normal Inbox, but I’ve not figured that out.

LATER : See the next post from me for a caveat.

 

[jasnw]

I'm going to have to back off of my last post. That approach was working using a copy in the rule on the Mac rather than a move. The move approach works, but (1) you have to fiddle around to get the "new mail" counter to show up, and (2) for some odd reason the "new mail" sound disappears. I even tried a work-around on the mail sound by putting a rule in early in the list of rules that just makes a sound for any mail. Not a peep until I went back to copy rather than move, in which case I got both the using new mail sound plus the sound I set up in a rule. But we knew Mail was a buggy piece of software.

 

[Fishrrman]

Re the message in post 9 above...

Some months ago, I went through the same thing with Yahoo, which hosts the servers on which my personal email account is located.

That is to say, before "the change", I was able to connect with Apple Mail.app using a POP account, "manually" established.

When Yahoo implemented the change, this would no longer work. I couldn't get a connection, no matter how I tweaked the settings manually.

Instead, the only way to "revive" Mail.app was to use Apple's "Internet Accounts" preference pane. Doing so sets up the Yahoo account automatically.
HOWEVER -- one loses the ability to "force establish" a POP account when you do this. All you get is IMAP.
(there may be "a way around this", but I wasn't able to find it)

I had always been a POP user previously. I was very reluctant to give this up.
I tried various other email apps (other than Mail.app). None worked.
But... in the end... I wanted my old email account to be functional again.

So... I did what I had to do.
That is... I set up the account as IMAP, and learned to live with it.

Some months later, I've become comfortable with IMAP.
Yes, I still miss "the old way of doing things" I had established with POP.
But the reality was... either accept the changes (to keep my old account and email address), or find a new email provider.

So... I accepted the changes.
And moved on.

 

[NoBoMac]

You might be able to use app-specific passwords: think those don't go away on May 30th. So if two-factor is turned on, can generate/use app-passwords.

 

[gecko579]

FWIW on my iMac (only) I access Gmail as POP from Apple Mail; all others are Gmail apps on iOS.

I have 2FA with app PW. In Apple Mail preferences, I list server as POP.gmail.com (usual credentials) and in the Gmail settings tab under “POP” I have POP active (I still use IMAP for browser and Gmail App but AFAIK all mail is downloaded to my iMac whether I view it before via iOS or not. Hope I don’t get squeezed (perhaps b/c I set it up with sign-in w Google? We’ll see…)

 

[JohnSFO]

Thanks Fishrrman. I did convert fully to IMAP and so far it's been good. I probably didn't need to fret so much now that I see the other side is fine too. One good thing to come from this is that I did a deep dive into my Gmail settings and shored up security, turned off settings that were only benefitting Google, and cleaned up my mailboxes during the switchover. For those who are still interested in POP accounts I believe comments #13 and #14 above about app passwords is a likely solution. Thanks to both for adding it to the thread.

 

[ThomasJL]

As of today, I cannot access my Gmail account using Apple Mail on my Mac. (I don't use e-mail on my iPhone.) I'm running macOS 10.15.7 and Apple Mail 13.4. Does anyone here know what I can do to regain access to my Gmail account using Apple Mail?

 

[Houpla]

Same problem here, want to keep using POP, much more logical than IMAP.

 

[Houpla]

Started working again without me doing anything…

 

[alcforest]

Same problem here, want to keep using POP, much more logical than IMAP.

I've reset four Apple Mail/Gmail POP accounts since May 30th, changed the previous passwords to an app passwords supplied by Google. For three of them, the change worked fine. The fourth one received emails OK with the app password, but kept coming up with errors on sending "cannot send message using the server xxxxx@gmail.com". I tried reinserting the app password, redoing the server settings on Mail etc but nothing worked. I then found the account was sending, but the emails were arriving labelled sent from a work email address that had never been associated with that Mail account. I am totally baffled as to why the sender address was changed, it happened within Google as the sender was correct when the messages left my laptop (I did ask the IT people at work, but they just said, helpfully, don't use Apple Mail!).
In the end I removed that one account and re-added it to Mail. It wasn't possible to add it as a POP account, so it had to be IMAP, which I really hate. The only thing I can think of I might have done differently for the problem account was that I know I turned off the "use less secure apps" on my Google webmail, and I can't actually remember doing that for the other three.
Conclusion, it is possible to use Mail accounts with app passwords and keep them as POP, but it might not always work.

 

[ThomasJL]

Started working again without me doing anything…

Same here. It started working again (without me doing anything) one day after I made my previous post.

 

[ThomasJL]

Same here. It started working again (without me doing anything) one day after I made my previous post.

Today, it stopped working again. I don't know what's going on.

 

[Houpla]

Yeah, I had to enable 2 factor authentication on myaccount.google.com and then it allowed me to create app password specifically for Apple Mail (you have to save it in Mail preferences, not when Mail asks you for password — otherwise it fails). After quitting and opening Mail, my POP access works again and I'm relatively happy (aside from being forced to give Google my phone number).