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This isn't the first time I've had problems with Apple Mail, but it usually is no more than once a year at worst, and it's been a while since last I had trouble. It's of a different nature each time.

I've lost almost two hours so far today, troubleshooting Apple Mail's inability to see available messages from GMail to download. I use POP vs. IMAP as I organize my email very carefully (I go nuts otherwise) and as I don't like ghost copies in multiple places or the potential for exceeding a data limit (POP erases on the server as soon as downloaded to the computer, so I only use the browser for current emails for a few weeks at a time -- though this time I waited almost two months before re-syncing Apple Mail by opening it to consolidate and organize messages from the start of my coast-to-coast move).

At first it wouldn't let me log in. I changed my Google password yet again, to one that is more secure, and once again enabled less secure apps as well as verifying that two-step authentication is not required (I do not have a smart phone or a laptop or a tablet). Too many other things to mention here, but I did force TLS certification, which previously was not required, yet to no avail.

I'm hesitant to delete and reinstate my GMail account in Apple Mail, as I'm not 100% confident it won't delete Apple Mail messages that are in local folders, even though I did clean out ALL inbox and sent messages this afternoon to make sure that anything previously downloaded from Yahoo or GMail is now organized into "On My Mac" by-topic folders.

I may run an Apple Mail backup tool and then take that chance though. Or maybe I'll get brave and upgrade to Big Sur, if it looks like enough stuff works on it yet. Not sure if a newer macOS big-number-version reinstates compatibility with GMail.

UPDATE: I found the Big Sur topic and know better than to upgrade as any of today's attempts to get Apple Mail and GMail to work together again.

Another possibility is to once again (for the first time in years) install Mozilla Thunderbird and make that my desktop mail client.

Note that my GMail account does show up as on-line in Apple Mail. I guess I'll do yet one more computer reboot, just in case of bootstrapping issues.

I've had this problem with Outlook, and it's a security setting in Gmail. The fix is to allow "Less secure apps" in the Gmail security settings. Worth a shot.

The problem is GMail.

My Spam account (old email address I give when I know I'll be spammed—but I want the info) is on AOL and it's been acting up these last 3 days, too. Sometimes it works; other times it doesn't but I don't give a damn.

About three weeks ago, the problem was Yahoo — took Verizon nearly two weeks to fix that one but they did. I had no problem getting it on my iPad, though. Yahoo mail screws up a couple times a year and I always promise myself I'll switch… and then mid–January comes around and I've been charged for another year. Maybe 2021 — or not.

Yep, I already set the GMail stuff to what it should be, so I don't see anything additional I can do at that end.

Just lost a couple of hours on my computer not rebooting, after the changes I made to try to figure out this email error.

At least that's taken care of now. As for Yahoo Mail, I use it only for emergencies, and yes, it fails twice a year.

As this is my first time opening the Apple Mail client since the day before I started my drive east for my new job, perhaps I should just wait a day or two and see if the problem sorts itself out.

I did take the recommendation to turn off "update in real time" as there's some talk of checking more than once every ten minutes causing an app to get flagged by Google as dangerous. I didn't set to manual update but rather to once an hour, but refreshing manually still sees "no new messages".

My particular error didn't show up in searches; only the initial problem with security, which I solved very quickly before I wrote my post. It's the inability to see new messages that is confusing, as it shows GMail as being on-line with correct credentials, and Apple Mail is no longer blocked.

It's worth pointing out that I'm able to send via GMail using Apple Mail, once I got the unsafe app blockage taken care of (and a new password).

I do not want to switch to an app password for incoming email as Google deprecates that, but perhaps it would fix things. Maybe IMAP would as well, but I'd rather try Thunderbird with POP before going that route, due to how poorly Apple Mail handles IMAP (too many disconnected copies and ghosts).

I think I know the problem, but not the solution. I have always used Ethernet for my internet, until I went on the road for my move east, and now in this house share. Almost no one has Ethernet here; it's almost an entirely WiFi based community in Durham. I suspect this is a conflict for my incoming email from GMail to Apple Mail, as some talk about changing one's DNS settings (which are inapplicable towards C3-5G WiFi).

I found a final hint that worked, after many that didn't:

When the lightning bolt shows up next to an account, click it to find out the problem.

I had done this earlier, when it showed that the account was blocked, but not since all the other troubleshooting.

The reason is that I am used to this symbol only being relevant when there are error messages in the app.

Clicking the lightning bolt downloaded all my messages from 22 SEP onwards. Checking for new mail didn't work!

Just lost a couple of hours on my computer not rebooting,

My Mac Will Not Shut Down

How to Reset Launch Services

1. Open Terminal and run these commands:
2. sudo /System/Library/Frameworks/CoreServices.framework/Frameworks/LaunchServices.framework/Support/lsregister -kill -seed -lint -r -f -v -dump -domain local -domain system -domain user -domain network
3. killall Dock
4. sudo mdutil -E /
5. Restart your Mac

Thanks Mike; my wording was probably ambiguous, as the actual problem was that it wouldn't boot up rather than that it couldn't shut down, but this is a good reminder for the latter situation, which I have experienced a few times over the past several years.

mhschmieder wrote: ↑Sun Nov 15, 2020 2:18 pm I found a final hint that worked, after many that didn't:

When the lightning bolt shows up next to an account, click it to find out the problem.

I had done this earlier, when it showed that the account was blocked, but not since all the other troubleshooting.

The reason is that I am used to this symbol only being relevant when there are error messages in the app.

Clicking the lightning bolt downloaded all my messages from 22 SEP onwards. Checking for new mail didn't work!

I think this was a general problem with Catalina. On the Macs I have it installed on, all email accounts in Apple Mail ignored new mail until I did this, or went to preferences, and turned off, then on, the option to automatically check for new mail. This happened with about 20 accounts on 5 different email services (including Apple). After that it was fine.

mhschmieder wrote: ↑Mon Nov 16, 2020 4:45 pm Thanks Mike; my wording was probably ambiguous, as the actual problem was that it wouldn't boot up rather than that it couldn't shut down, but this is a good reminder for the latter situation, which I have experienced a few times over the past several years.

Actually, I've used it to fix both conditions.