Mail: Misleading error messages on all devices

[Buadhai]

I didn't know where to put this, but it's a problem that has been plaguing my wife and I for some time. It happens on our MBAs running Sequoia and on our iPhones and iPads. We each have email accounts provided by the web host that we use for our websites. That email works fine no matter where we are except at our condo in Cha Am, Thailand where we get the following:

We know our passwords are correct because they work everywhere else.

So, what's going on? I had a look at Mail's connection doctor and see that when here at the condo it cannot connect to the web host's IMAP server. The mail log says:

READ Nov 29 13:48:24.251 [kCFStreamSocketSecurityLevelTLSv1_2] -- host:mail.mgnewman.com -- port:993 -- socket:0x600002686700 -- thread:0x6000016f2400
3.143 NO [AUTHENTICATIONFAILED] Authentication failed.

Looks like a password problem, right?

Well, no. When I switch to a VPN, it works fine. Why? Well, at out condo we share a single public IP address with 350+ other units. It appears that someone is being naughty which has resulted in our IP address being blacklisted here and there. Oddly, both Apple Mail and Gmail work fine with the same IP address.

It would have been nice if Apple's Mail error message were not so misleading.

 

[FreakinEurekan]

All macOS knows is that the password isn't being accepted. Can't blame Apple for that error message; blame whomever was spamming in your condo.

 

[Buadhai]

All macOS knows is that the password isn't being accepted. Can't blame Apple for that error message; blame whomever was spamming in your condo.

That's the point. All they know is that there is an authentication error which can have several causes, one of which is an incorrect password. Apple simply assumes that it is a password problem which, in this case, was incorrect and misleading.