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Buadhai

macrumors 65816
Original poster
Jan 15, 2018
1,117
434
Korat, Thailand
Now and then Mail (or the OS) display alerts asking the user to re-enter the password for a specific email account. Some of them look like this:

Screenshot 2024-06-08 at 3.17.18 PM.png
or this
Screenshot 2024-06-08 at 3.21.05 PM.png


So, you enter a known-good password only to have it fail, over and over again.

When this happened to me recently I opened up Connection Doctor to see what was up:

Screenshot 2024-06-08 at 3.24.02 PM.png


As you can see, Mail can't connect to either the IMAP or SMTP server for an email account that uses a domain I own and which is hosted by HostGator.

You can ask Connection Doctor to Show Detail, but that probably moves by too fast to read. So, you can ask it to Log Connection Activity and then Show Logs in the Finder.

I did that and had a look at the log to see if I could find out what was happening. Here it is:

Code:
Jun 08 16:13:01.230 [kCFStreamSocketSecurityLevelTLSv1_2] --
host:mail.MyDomain.com -- port:465 -- socket:0x600002d7cd80 --
thread:0x600001197340 550-"[110.nn.nnn.212]:51301 is in an RBL on
bl.pro1.websitewelcome.com, see 550 Blocked - Botnet Detention"

So, the problem is that my IP address is blacklisted by websitewelcome, which, I believe, is run by HostGator.

That IP address is provided by NT, the Thai government's National Telecommunications agency. It is shared by 350+ apartments at a condo where I own a unit. Little chance of getting that fixed. What to do?

How about trying a VPN?

Screenshot 2024-06-08 at 3.24.39 PM.png


Sure enough, as soon as I enabled the VPN, the nasty red dots changed to green and the spurious password alerts disappeared.

So, why does Mac Mail assume that this authentication failure is password related? Only the human (?) who wrote the code can tell you that. But, in my experience, Mac Mail seems to treat every mail server authentication error as a password error, even when the server reply indicates otherwise.

Same thing happens when Mail inexplicably tries to initiate a TLS session with the iCloud SMTP server using Port 25 (long obsolete - Port 587 is preferred as it is encrypted).

One thing I can't figure out is why HostGator blocks that IP address only now and then. The IP address never changes and whenever I've checked, it appears on a number of blacklists.

Just another mystery.
 
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