Hello all! So we have a new Exchange 2013 install with a few users. Everything was working fine except for Outlook which could not send email. When clicking on the send/receive button an error came up saying that it could not connect, even though the bottom right of the window said that it was connected.

After fooling around with the outlook anywhere settings I was able to get it working. Before long the connection to Exchange dropped and asked for a username and password. Now it doesn't accept the username and password and doesn't give an error. When connecting via OWA everything works fine.

So I went to control panel, clicked on the mail icon and deleted the exchange server account and tried to add it again. Unfortunately I cannot add it. It asks for the username and password as part of the setup but will not accept it even though I know that the credentials are correct. Again OWA works fine.

Here are some other things that I did but not sure if it caused this problem: Changed passwords and used an exchange cmdlet to configure email forwarding for a couple of accounts (which didn't work). All this was just before my authentication issues began. It seems as though Outlook is not communicating with the Exchange server even though I can login to OWA using the FQDN of Exchange.

Any thoughts???

You have no other Exchange servers in the organization?

Have you installed a valid certificate?

Does the certificate properly match the InternalURL and ExternalURL settings on the various virtual direcotries?

Is the client access server configured with the proper AutodiscoverServiceInternalUri property, and is that name in your certificate?

Is your Outlook Anywhere properly configured and, in particular, does the certificate principal name properly match the certif

Are you trying to setup the profile manually in Outlook by specifying the server name? If so, you need to let Outlook use autodiscover, as the end point is the mailbox guid @ smtp domain and not the server name.

Thanks Ed. Not sure if it is a certificate issue. We were connected fine for a couple of weeks and then yesterday outlook disconnected from the server and asked for a password. Now it won't authenticate. I wiped out the profile and tried again and during setup it asks for the email address and password but still won't accept it. It eventually says "The connection to the Microsoft Exchange Server is unavailable. Outlook must be online or connected to complete this action".

Yes, after i wiped out the profile, that used to work fine, I proceeded to setup a new account. It automatically recognized my email account. After clicking next it goes through the configuration process and I get a popup that says "You must restart Outlook for these changes to take effect." After hitting OK it asks for my username and password in a window titled "Connect to mail.mycompany.com". It auto populates my email address and I type in my password. When i click OK the windows pops right back up asking for the same information. This is as far as i get. If I hit cancel it says "The connection to the Microsoft Exchange Server is unavailable. Outlook must be online or connected to complete this action".

Everything was working fine before yesterday. The only thing that changed was a password reset on AD, and a few CMDLETS in exchange to store and forward email to an external email account.

Thanks!

Try clearing the cached credentials on your Windows profile.

I'll try that. Thanks.

Thanks Rajith but that didn't clear the issue. Ed, I'll double check the certs.

OK, we don't have any other exchange servers. We have 3 certs that were installed with the load (Microsoft Exchange Server Auth Certificate, Microsoft Exchange, and WMSVC). I haven't install any yet. The first is for smtp services. The second is for SMTP, POP, IMAP, and IIS. The third doesn't have any services checked. Onlty the Misrosoft Exchange  cert has the FQDN of the mail server and it is in the section 'Subject Alternative Names'.

The IIS certificate is the one Outlook must trust since Outlook must use Outlook Anywhere with Exchange 2013.  There are other Outlook Anywhere settings that must also be configured.

Looks like i may have to perform a fresh install. There seems to be no resolution readily available and it's taking too much of my time. Thanks guys for your feedback.

Good luck.