Created a new Exchange 2019 server in a new domain - the old server was 2010 but there had been a failed attempt to install Exchange 2019 in that domain (which isn't supported directly) which wouldn't allow an Exchange 2016 interim installation. After
spending some time trying to get it to work, we gave up and elected to create a new domain and new Exchange 2019 installation instead as this domain has been upgraded many times back to NT 3.51.
In any case, the domain and server were built and was tested with the Exchange Connectivity Analyzer which it passed for the main domain name. Email flow is working but we have other domains on this server so, in migrating the first one, setup an SRV record
in that domain's DNS that points the autodiscover to the primary domain as the certificate only has the primary domain's DNS records in it. This is how Exchange 2010 was setup and it worked.
Again, this was tested with Exchange Connectivity Analyzer and it passrd. So the certificate works, autodiscover works from the Analyzer, phone/mobiles work but we are having trouble with Outlook.
The current issue is with an Outlook 2013 client. They have an email with the secondary domain name but Outlook won't connect despite everything looking proper. We set the Exchange Proxy settings with basic authentication but keep getting the error message"The connection to Microsoft Exchange is unavailable. Outlook must be online or connected to complete this action".
We have been looking into authentication issues but the account works on mobile with the same settings (I know that is ActiveSync vs. a full Exchange connection but it verifies the account is working). We have also looked at the authentication methods, ensure
Outlook Anywhere is configured and turned on, that the split DNS and External and Internal URLs are setup, etc. The client is external but all the ports are open (unless there is a new one that we are unaware of but then the analyzer should fail too shouldn't
it?) and the DNS names resolve on this client.
Basically it all looks like it should be working from the server end and from running the analyzer but the client cannot setup an account for some reason.
We are wondering if anyone else ran into anything similar setting up Exchange 2019 or, if it's not a version issue, even 2016 or 2013? We are continuing to search for a solution but we are running out of things to check so I thought maybe one of you have been
down this rabbit hole before and could help us out.
Thanks in advance.