outlook 2013 keeps prompting for password on exchange email acct after installing windows server essentials

Question

Hello all,

I have a win 2012 r2 server running exchange 2013. all was working fine. I put windows server essentials on it and my exchange account in outlook began prompting for a password and i couldn't get it to stop.

Trying to load the Exchange management shell I get "Failed to connect to an exchange server in the current site.
Looking at the running services all the exchange services seem to still be installed and running but I cannot connect to the exchange server with outlook.
when i try to setup a exchange account I get the message " an encrypted connection to your mail server is not available. Click next to try an un-encrypted connection. After that it fails and says "having trouble connecting to your account

I uninstalled the windows server essentials from the server but the exchange management icon still doesn't work.
I guess I F.U.B.A.R. the exchange server is there a reinstall option to repair it I really only need to get my calendar info back.
Any thoughts are appreciated.

Thanks for any ideas

Answer 1

Hi @Mac Johnson ,

Are you able to access ECP or OWA using your administrator or the user account?
Have you check the Event Viewer on the Exchange server and see if there are any relevant error events?
Which CU of Exchange 2013 are you using?

Trying to load the Exchange management shell I get "Failed to connect to an exchange server in the current site".

Based on my research, this error could be related the .Net framework 3.5 and 4.5 on the server. Please go to Server Manager > Add/Remove Features, install the .Net 3.5 and 4.5 as shown in the image below:

In case they have already been installed, please try removing them, reboot the server, then install them again and check the result after a reboot.

Here is a similar thread for your reference: Error “Failed To Connect To An Exchange Server In The Current Site” While Running Exchange 2013 Shell.

As regards to the password prompt issue in Outlook 2013, may I know if the Outlook is installed on the same machine with Exchange?
What's the detailed build number of it? You can view the version information via File > Office Account > About Outlook.

To help narrow down the issue, please run the Test-E-mail AutoConfiguration in Outlook and share the output in the Log tab(Be sure to remove all private information like email addresses or domain name. ):

1. While Outlook is running, hold down the CTRL key and then right-click the Outlook icon in the system tray, select “Test Email Autoconfiguration”.
2. Confirm that your email address is in the address field, uncheck “Use Guessmart” and “secure Guessmart authentication” boxes. Then click the “Test” button.
3. Once it runs, check the Log tab:
   

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