Win server 2019 - Outlook cannot connect to on prem Exchange server when terminal server is in different VLAN RRS feed

  • Question

  • Hello there,

    Sorry for my english.

    We are facing a weird problem on our new terminal server.
    Terminal server is Win 2019, there is installed Office 2019 Standard 32 bit via ODT.

    In our environment we using VLANs, terminal server is located in VLAN 9 (servers). But also there is an old SBS server with Exchange 2010 wich is located in VLAN 10 (users). Since new year we have started migration process. So we are replacing old VMs with new one to Win srv 2019. And SBS is the last one which is not migrated because there is on prem exchange.

    We will migrate exchange to O365 at the end of this year.

    So now to the problem what we have. When users try to open outlook on terminal server, outlook wont open. And it says that he is trying to get information from Exchange server, that is unable to connect to exchange server etc.

    But when I move term server to the same VLAN as SBS, outlook will open immeadiately. So we have checked our router, its FortiGate 60F, there is no blocking rule. Traffic is allowed between these two VLANs.

    I would appreciate any suggestions, ideas anything.


    Wednesday, July 1, 2020 7:22 AM

All replies

  • Hi Swabinsky,

    Sorry, I'm not familiar with VLAN, could you tell me whether the users‘ PCs are in the domain?

    For such Outlook connectivity issues, please use "Test Email Autoconfiguration" to test autodiscover when they are in different VLANs, here are the steps:

    1. Locate the Outlook icon in the notification area, hold the CTRL key, right click the icon, and then click Test E-mail AutoConfiguration.
    2. Enter the user's email address and password, only choose Use AutoDiscover. 
    3. View the result on the Log tab.

    Be free to post some snapshots here with personal information covered.


    Eric Yin

    Please remember to mark the replies as answers if they helped. If you have feedback for TechNet Subscriber Support, contact tnsf@microsoft.com.

    Thursday, July 2, 2020 5:39 AM
  • Hello Eric,

    The users' PCs are in the domain. The terminal servers' are in domain too.

    Thanks for suggestion, I gave it a shot and everything is ok. Autodiscovery works.

    But this somethimes happens... Sorry we have our terminal in Czech language, so error code is in Czech too.

    But it says, that Outlook is trying to load data from Microsoft Exchange server and name of on prem server.

    Damn I dont have verifyied my account yet. I will upload Screenshot later. Thanks

    Friday, July 3, 2020 12:12 PM
  • Hi,

    I'm here to confirm with you if your issue has been resolved. If the problem is successfully solved, you can share your solution and mark them or the helpful reply as answer, this will make answer searching in the forum easier and be beneficial to other community members as well.

    This Exchange Server 2010 Forum will be migrating to a new home on Microsoft Q&A, please refer to this sticky post for more details.


    Eric Yin

    Exchange Server 2010 forum will be migrating to a new home on Microsoft Q&A! We invite you to post new questions in the new forum.

    For more information, please refer to the sticky post.

    Thursday, July 16, 2020 8:50 AM