Outlook 2016 Autodiscover Exchange 2013 over Always On VPN

PeterL 86 Reputation points
2020-08-27T14:18:53.27+00:00

When creating an Outlook profile for Exchange 2013 while onsite, the autodiscover process works completely. If I am off-site and connected using Microsoft Always On VPN the process fails as per the following:

  • Autodiscover gets correct email address - click next
  • Establishing network connection - works
  • Searching for [email address] settings - prompts for credentials
  • Enter credentials - click OK
  • 'You must restart Outlook...' message - Click OK
  • Logging on to the mail server - Generates message 'Outlook cannot log on. Verify you are connected to the network and are using the proper server and mailbox name' - click OK
  • 'The action cannot be completed' message - click OK

The same process works without a problem when connected to the network while onsite. Is the process treated as an external connection when connected over Always On VPN? Any other pointers appreciated.

Current environment:
Exchange 2013 CU23
Client – Windows 10LTSC with Outlook 2016
Connected via Microsoft Always On VPN
Device - split tunnel
User - forced tunnel no exceptions

Regards,

Pete.

Outlook Management
Outlook Management
Outlook: A family of Microsoft email and calendar products.Management: The act or process of organizing, handling, directing or controlling something.
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Exchange Server Management
Exchange Server Management
Exchange Server: A family of Microsoft client/server messaging and collaboration software.Management: The act or process of organizing, handling, directing or controlling something.
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Accepted answer
  1. Lucas Liu-MSFT 6,161 Reputation points
    2020-08-28T03:05:52.367+00:00

    Hi Pete.
    According to my research on Always On VPN, if you connect to the Exchange server through Always On VPN, it will be an external connection.
    According to the information you provided, I think this error is caused by the Autodiscover service not working properly. Please following the steps and see if the issue is resolved.

    1. If you activate the firewall, please make sure that your firewalls allow the traffic that is necessary for both VPN and RADIUS communications to function correctly.
      For more information: Always On VPN technology overview
    2. If your Outlook client is connecting from outside your network or the client isn’t domain-joined, the Autodiscover.domian.com has to be in DNS and in the certificate. You can also create SRV records if you're don't want to adding Autodiscover domains to your certificate and DNS.
      21089-2222.png
    3. You could use ExRCA to detect whether Outlook can connect normally and whether the automatic discovery service is working normally. If an error occurs, ExRCA will also provide a detailed error message, which will be of great help to our problem solving.
      About ExRCA: Microsoft Remote Connectivity Analyzer.

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