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Can't connect Office 365 Outlook client to Exchange 2016 On Premise Server RRS feed

  • Question

  • We have a On Premise Exchange 2016 server with external MX record pointing to our Exchange server.  We are already receiving external email successfully and I've already connected a Outlook 2007 client.

    However, now I'm trying to connect a client using Outlook via the Office 365 subscription,  but am getting the following error message;

    Please advise.

    Thursday, September 26, 2019 12:51 PM

Answers

  • I guess the Outlook 2007 client and Office 365 Outlook client are both domain-joined clients, is that true?

    If so, could you reproduce the issue in other non-domain-joined clients? 

    Did you configure the account in Outlook using Autodiscover or manual method?

    What is the result if you test the Outlook Autodiscover in ExRCA?

    In Outlook 2007 client, could you please check the connection status? 

    Open Outlook 2007 client, long press the Ctrl and click the Outlook icon:

    Regards,

    Manu Meng


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

    Friday, September 27, 2019 10:30 AM
    Moderator

All replies

  • Hi

    Where are your other records pointing for autodiscover and the other protocols? Did you perhaps enable mapi over http and configure mapi virtual directory and its DNS as well?


    Hope this helps. Please remember to click “Mark as Answer” on the post that helps you, and to click “Unmark as Answer” if a marked post does not actually answer your question. This can be beneficial to other community members reading the thread.

    Thursday, September 26, 2019 12:53 PM
    Moderator
  • My local DNS server has a CNAME for autodiscover.  ad.mydomain.com is my internal domain name, with mydomain.com being the external one.

    In my browser, when I visit https://autodiscover.ad.mydomain.com/autodiscover/autodiscover.xml, I'm prompted for a username and password.  If I enter the username/password for the client I get a screen showing

    <Autodiscover xmlns="http://schemas.microsoft.com/exchange/autodiscover/responseschema/2006">
    <Response>
    <Error Time="13:44:18.7451007" Id="2793805734">
    <ErrorCode>600</ErrorCode>
    <Message>Invalid Request</Message>
    <DebugData/>
    </Error>
    </Response>
    </Autodiscover>

    I don't recall enabling this 'Did you perhaps enable mapi over http and configure mapi virtual directory and its DNS as well?'

    Thursday, September 26, 2019 12:58 PM
  • hello

    your cname give autodiscover.domain.com ? where your mail is user@domaine.com  ?

    in exchange, could you give this information :

    get-clientaccessservice | fl AutoDiscoverServiceInternalUri

    and prompt the result ? (this is the SCP value, the first query for internal domain client)

    Olivier.

    Thursday, September 26, 2019 1:35 PM
  • Thursday, September 26, 2019 1:50 PM
  • this uri is working on IE ? (like the other test)

    you don't have a certificate error ?

    Thursday, September 26, 2019 2:37 PM
  • Yes I do have the certificate error

    Your connection is not private

    Attackers might be trying to steal your information from advexch01.ad.mydomain.com (for example, passwords, messages or credit cards). Learn more

    NET::ERR_CERT_AUTHORITY_INVALID

    Do I need to purchase a SSL certificate? Or can I use the self signed one?

    Thursday, September 26, 2019 3:16 PM
  • if you use a self signed, you have to install it on each computer by GPO.

    As its a self sign, its his own authority.

    for testing : go to your MMC certificate, computer side, and add it in trusted authority.

    Friday, September 27, 2019 6:36 AM
  • I guess the Outlook 2007 client and Office 365 Outlook client are both domain-joined clients, is that true?

    If so, could you reproduce the issue in other non-domain-joined clients? 

    Did you configure the account in Outlook using Autodiscover or manual method?

    What is the result if you test the Outlook Autodiscover in ExRCA?

    In Outlook 2007 client, could you please check the connection status? 

    Open Outlook 2007 client, long press the Ctrl and click the Outlook icon:

    Regards,

    Manu Meng


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

    Friday, September 27, 2019 10:30 AM
    Moderator
  • Kinly Check This

    1. Issue is with Internal network or external?

    2. If internal then try creating hostfile entry on client machine for "autodiscover.domain.com" pointing to IP address of your first installed CAS server

    3. If above works then there is an issue with DNS

    4. Check if proper DNS record for Autodiscover is configure, moreover if you've only exchange Onprem then Delete the "Autodiscover.domain.com" CNAME record and create Host A record for the same

    5. Run below command and check if MapiHttpEnabled:

    Get-OrganizationConfig | fl name, *mapi*

    6. If enabled then try to disalbed it and ran IIS reset and check the behaviour

    7. Run EXRCA.com test and check the connectivity

    8. Also, check your EWS, OAB, OutlookAnywhere namepsace and its corresponding DNS entry --> It should point to your internet facing CAS server

    Regards,
    Citrix Vdi and Windows Server 2019 Expert

    Wednesday, October 2, 2019 3:41 PM
  • Just checking in to see if above information was helpful. Please let us know if you would like further assistance.

    Regards, 

    Manu Meng


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

    Monday, October 7, 2019 7:39 AM
    Moderator