[REQUEST] Unusual cannot connect to POP or IMAP issue

[MrEastwood]

Client computer, Win 10 Pro, Outlook 2013. They have an externally hosted POP/IMAP email for their office. Not my choice, I've suggested they move to something better ala Hosted Exchange but they don't want to switch. I can log into the account using webmail (not OWA, this is not Exchange, just plain webmail) just fine. Thus I know the username and password are working.

Delete the Windows email profile, create a new one from scratch. Used their instructions for both POP and IMAP, neither work, they just keep looping over and over asking for username and password. I called their tech support and they confirmed the settings were correct. They changed the password for me and the new one works on webmail.

Tried it on my own test machine, Win 10 Pro, different version of Outlook, 2016. I am in a completely different city, so there's literally nothing the same here. Anyhow, I can log into webmail just fine. However, the same issue occurs using Outlook 2016, I've double and triple and quadruple checked the settings. Called their tech support back, asked them if they'd remote in to check my settings but they said "we don't do remote support", huh? This is an ISP that is also an MSP... ok wow. So I had her read and confirm their tech support web page URL settings and she confirmed what the previous support tech said, the settings are all correct.

No, I'm not making any typos. Tried both POP and IMAP on both my test machine and client machine, same issue. No SSL on incoming, only on outgoing. Ports are set correctly, SSL is set correctly. I've done this a bazillion times over my 30 year career and never had this much trouble.

FYI all the other 20-odd staff are using their Outlook 2013 and 2016 with these accounts and it's working fine with same settings! Am afraid that if I remove another staff profile and try to re-add it, I will get the same problem so I don't want to do that.

Next, I telnetted into their pop server, and could telnet into it, I could connect fine and set the user, but when I set the password it says "-ERR could not determine server". I couldn't find anything useful about that error, perhaps it's a clue?

For now, customer is using web mail until I get this solved. Any further suggestions?

 

[Markverhyden]

So you are not using autodiscovery? Manually setup the server?

 

[MrEastwood]

Correct, manual setup.

 

[Markverhyden]

Given you description of the provider I'd think that maybe it's some kind of cert issue. Anything in Event Viewer? For grins have you tried another client like Thunderbird? You can do that on your end first.

 

[GTP]

have you tried another client like Thunderbird?

This ^^ see if the problem replicates.

 

[MrEastwood]

Great idea will try that

 

[MrEastwood]

Found the answer.

I tried Thunderbird and the same issue happened. So I noticed that their tech support was open late so I phoned them again for the third time to suggest that they look into testing a few things on their end. This tech checked my settings (as did the others) but said no, those aren't the correct POP/IMAP servers... what?! It wasn't even a misspelling, the names on their support site are imap.server.com and pop.server.com, but in reality the actual server is like host4.server2.com. Crazy.

Turns out not only are their support web pages wrong, but the first two techs didn't even know this information.

 

[NJW]

It wasn't even a misspelling, the names on their support site are imap.server.com and pop.server.com, but in reality the actual server is like host4.server2.com.

I think @Markverhyden got it. I'll wager that the certificates are for the server domain name, not for the imap and pop subdomains. If you'd connected on the non-TLS ports, it probably would have worked.

 

[MrEastwood]

No I didn't mention it but I tried that, didn't work.

 

[Markverhyden]

Having server name "change" is not unusual. I've seen it before, redirects. Fairly common. Did you log into another machine to see what they actually have for settings?