Hi,
Outlook cannot connecting to Exchange server may happen for many reasons.
To troubleshoot the issue, please first check you can connect to Exchange server properly from OWA. If you can connect via OWA, please also try switching your Outlook to online Exchange mode and then check if the sync issue will be gone. If the issue disappears in online Exchange mode, it means the OST file might be corrupt. We can try to recreate the OST file to resolve the issue.
In addition, if you are in an external environment, please also check if Outlook Anywhere is enabled. You can follow the instructions in the following article to do it:
If you can't connect to Exchange using OWA, it's more likely a server side issue. I'd recommend you post a new question in the Exchange forum for further assistance:
https://social.technet.microsoft.com/Forums/office/en-US/home?category=exchangeserver
The reason why we recommend posting appropriately is you will get the most qualified pool of respondents, and other partners who read the forums regularly can either share their knowledge or learn from your interaction with us. Thank you for your understanding.
Steve Fan
TechNet Community Support
It might be possible that the MAPI key (which enables Outlook to synchronize with Exchange) has been deleted due to the System crash. So, in order to establish the connection, you need to Reconnect the OST file to the original MAPI profile and then reconnect then MAPI profile to Exchange Server.
If the above method fails to resolve the issue, then the best option for you would be to take the help of any professional OST to PST Conversion Software, which will help you to Extract data from your OST file and convert it to PST file which you can import back to your Outlook to establish the connection with Exchange Server again.
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