With the ill advised and inexplicable removal of the Exchange account setup dialog from Outlook 2016, we are left trying to get Outlook setup with autodiscover on an SBS 2011 box running of course Exchange 2010.
We have tried this with a CNAME for autodiscover and then removing that and using an SRV record but neither has allowed us to successfully setup an Outlook client remotely. We can resolve and see the autodiscover settings. However, testing using Outlook
2010 as a testbed (no 2016 to test with alas at this point), Outlook 2010 cannot finish setting up the account as it bails out during the following process:
We enter all the information (email address, password, etc), it goes out to find the autodiscover record, which DOES work, it prompts us to allow the website to configure the settings, which we allow. It then prompts for credentials, which it accepts and
then pops up what I believe is the first part of the problem:
You must restart Outlook for these changes to take effect.
After we hit okay on that box, we get a green check next to the Search for... section on the setup window. BUT we then get this popup, which I believe is related to the fact it cannot resolve the internal .local dns name of the server without using RPC over
HTTP, which won't work until Outlook is restarted...blah blah:
Outlook cannot long on. Verify you are connected to the network and using the proper server and mailbox name. Etc...
Once we hit okay to THAT, we are prompted for the Exchange server name and Mailbox name. At this point, the Exchange server name shows the Exchange servers internal .local name, and the mailbox shows =SMTP:name@mail.com and the usual Check Name box. Which
of course doesn't work, because it has to use RPC over HTTP to connect and it doesn't get to that dialog. So, it barfs and then says
The name cannot be resolved. The action cannot be completed.
Now normally you could just check the Manually configure server settings, go into the setup, enter the RPC over HTTP information, check the server name, and all is right with the world. But, Outlook 2016 doesn't LET ME do this. So we have to get this working
all the way through.
Before you ask, we use a self signed cert (certs are a damned rent-seeking racket) which we can install without a problem so it's not a cert mismatch issue, BUT that also means the Microsoft web site - which does let you ignore trust for SSL on many things
- doesn't let you ignore it for testing the Outlook side of things. So I cannot get past that, so no diagnostics to give you there.
So, what advice is there to resolve this? I figure if we can get Outlook 2010 to autoconfigure properly for remote clients, then it should work as well for 2016. Besides, this should sort of work for Outlook 2010 anyways I would presume. Somehow the RPC
over HTTP isn't being taken into account in a usable way during autoconfiguration. Any help would be appreciated, I have tinkered with this for a long time with no breakthrough. And prior, we really didn't have to deal with this, because we would always manually
setup the account anyways and enter the Outlook Anywhere information. But, Microsoft removed that option (for unknown reasons), so...
