Catalina broke Mac Mail for my business domain...

[^^BIGMac]

After upgrading my new MacBook Air to Catalina my email doesn't work...for my domain. I've had my website and email hosted with the same hosting company for 20 years and now for my email hosted at that same company Mac Mail doesn't work. Constantly stuck on "checking for mail", doesn't delete email from other devices after deleting from the MacBook, can only quit after doing a force quit...stuff like that. It works for other providers including iCloud and another website I have hosted someplace else but not at my main domain. WTF?

I have contacted Apple Support and have been working with a Senior Advisor who has elevated the issue to "Engineering" who has been screwing around collecting data etc. for the past 2 1/2 weeks. They have no idea. So, I rolled back the OS to Mojave which is the OS that was shipped with the computer and everything works as expected.

How in the hell can Apple screw this up? And how can it be only be affecting the email account hosted by one single hosting company? Seems the issue has to run deeper that this! I have talked with the hosting company and they checked everything on their end, my settings and everything is the same and as should be. Catalina is a POS.

One wonderful suggestion Apple made was to change my email address ... i.e. use iCloud mail or Gmail or something else. Not really a good solution.

So, I wait. I have offered to setup a test email account at my hosting company and provide Apple with all the setting/PW so they can test until their hear is desired. Waiting to hear if they want to try that.

Anybody else experience anything bizarre like this? Any suggestions? I'm out of ideas.

 

[BrianBaughn]

Yes…in prior versions of macOS…and if this is the first time you've had Mail issues congratulations on a long winning streak.

Did your hosting company say that they have customers successfully connecting via Mail in Catalina? That seems like an important point. If they haven't verified it works what good are the "correct" settings? You shouldn't try it again in Catalina unless they can confirm they've seen it work.

Since all my mail is either IMAP or Exchange these days, and I don't make what I consider to be the mistake of storing any mails "On My Mac", for past issues I have gone as far as removing all my email accounts, deleting the items in my ~/Library/Mail folder (user account Library/Mail) then re-adding the email accounts and letting ALL the old mail re-download.

Perhaps someone else has a good idea for a quick fix.

 

[^^BIGMac]

My hosting company isn't a fan of Mac Mail. They hadn't heard of the issue before so they are really no help in that regard.

This is an Apple issue and I just can't even believe it could happen.

What happened to "it just works"? Screw you Apple.

Don't you love talking to Apple Support and always the same response, --- "jeez I have never heard of that problem"...

 

[bcomer]

I use Thunderbird and it has been very stable.

 

[BrianBaughn]

What is the platform, Microsoft Exchange Server 2007 or something?

 

[^^BIGMac]

What is the platform, Microsoft Exchange Server 2007 or something?

I actually don’t know will ask.

 

[cramphal]

I'm having the same problem! cannot get to my work domain from MacBook Pro after upgrading to Catalina Pro. Affects my intranet and email accounts. Glad to know that I'm not the only one.

 

[^^BIGMac]

I'm having the same problem! cannot get to my work domain from MacBook Pro after upgrading to Catalina Pro. Affects my intranet and email accounts. Glad to know that I'm not the only one.

So, what is your alternative/solution? Mine was to roll the computer back to Mojave. Not the best solution but for now that's what I did.

 

[cramphal]

I'm able to route to the domain while connected to a work VPN. Other PCs and MACs on my network can route to the domain fine outside of the VPN. I get an error when I try to ping or traceroute to the domain as the 'operation is not permitted' from the terminal when not connected to the VPN. I checked all settings, turned off all firewalls, and even connected to other networks, but nothing worked. it's pretty weird.

 

[^^BIGMac]

Apparently my issue is that apparently the mail server is running on an old (ancient) windows 2003 machine and I guess something isn’t playing nice with Catalina. Doesn’t make sense to me.