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Outlook 2016 is not connecting to Exchange 2016 RRS feed

  • Question

  • This morning in my lab I built a new Active Directory with Server 2016. On a separate Server 2016 VM I installed with Exchange 2016 CU14.  On a third VM which I added to my AD; a workstation running Windows 10, 1809, and Outlook 2016.

    I log into the workstation with an account that has a mailbox on the Exchange system.  I launch Outlook and Outlook successfully built a new Outlook profile using autodiscover.  When I launch Outlook for the first time to retrieve my email I  receive the error: 

    Cannot Start Microsoft Outlook. Cannot open the Outlook Windows. The set of folders cannot be opened. The file <path>.ost is not an Outlook data file (.ost).

    Looking at the IIS logs I can see the workstation connecting to the autodiscover virtual directory endpoint but no other connections to the other Exchange virtual directories endpoints are made. I then perform a fiddler trace and see Outlook successfuily downloading the the autodiscover xml file and then the error appears.  Outlook never makes a connection to the mapi over http endpoint or rpc over http endpoint.

    I have disabled the Windows firewall on all of these machines and with it being my lab on an internal network no other security software is running on these VMs.  I am able to log into OWA from this workstation to this test account which outlook is not working.  I am unsure why Outlook 2016 is refusing to connect to any of the Exchange mailbox endpoints.  Any insight in how to fix my issue would be most helpful.

    Thanks,

    Joel

    Sunday, September 29, 2019 8:45 PM

All replies

  • Hi Joel,

    What's the Outlook build number? Is it the latest version?

    Do other users encounter the same issue? Or issue only exists in one user?

    Is there any proxy server? 

    For troubleshooting:

    Please run the following command to get the virtual directory settings of OA and MAPI/HTTP and let me know the result:

    Get-MapiVirtualDirectory | fl *auth*,*url*
    Get-OutlookAnywhere | fl *auth*,*hostname*


    Regards,

    Manu Meng


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    Monday, September 30, 2019 7:37 AM
    Moderator
  • Manu, I am running the latest version of Outlook 2016. I verified that by running Windows Update and there were no additional updates for Office which needed to be downloaded. This issues occurs with all the users within my lab. None of them can connect to Exchange with Outlook. This is an internal lab and they are not connected to the internet in anyway. So there is no proxy present on the network. All the VM are on the same subnet and virtual switch. Here is the powershell output you requested. Get-MapiVirtualDirectory IISAuthenticationMethods : {Ntlm, OAuth, Negotiate} InternalAuthenticationMethods : {Ntlm, OAuth, Negotiate} ExternalAuthenticationMethods : {Ntlm, OAuth, Negotiate} InternalUrl : https://e2k16.lab.local/mapi ExternalUrl : Get-OutlookAnywhere ExternalClientAuthenticationMethod : Ntlm InternalClientAuthenticationMethod : Ntlm IISAuthenticationMethods : {Basic, Ntlm, Negotiate} ExternalHostname : InternalHostname : e2k16.lab.local
    Monday, September 30, 2019 12:11 PM
  • Manu, I am running the latest version of Outlook 2016. I verified that by running Windows Update and there were no additional updates for Office which needed to be downloaded. This issues occurs with all the users within my lab. None of them can connect to Exchange with Outlook. This is an internal lab and they are not connected to the internet in anyway. So there is no proxy present on the network. All the VM are on the same subnet and virtual switch. Here is the powershell output you requested. Get-MapiVirtualDirectory IISAuthenticationMethods : {Ntlm, OAuth, Negotiate} InternalAuthenticationMethods : {Ntlm, OAuth, Negotiate} ExternalAuthenticationMethods : {Ntlm, OAuth, Negotiate} InternalUrl : https://e2k16.lab.local/mapi ExternalUrl : Get-OutlookAnywhere ExternalClientAuthenticationMethod : Ntlm InternalClientAuthenticationMethod : Ntlm IISAuthenticationMethods : {Basic, Ntlm, Negotiate} ExternalHostname : InternalHostname : e2k16.lab.local

    Did you enable the MAPI/Http in global?

    Get-OrganizationConfig | fl MapiHttpEnabled

    Check the site bindings in IIS manager, ensure that the correct cert are assigning to https service on Exchange Back End and Default Web Site.

    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.

    Wednesday, October 2, 2019 8:23 AM
    Moderator
  • Manu,

    As you suggested I ran the command Get-OrganizationConfig and verified MapiHttpEnabled was set to true. 

    I check the site's https binding on both the Default Web Site and Exchange Back End. Originally both sites were using the self sign certificated which is created during the install of Exchange.   As this issue might be caused by certificate miss match I installed an enterprise CA on my lab DC.  In a single certificate request I added the DNS names for autodiscover, outlook and the FQDN of the server.  From that request I created a valid certificate from my enterprise CA and assigned that certificate to the Default Website/Frontend.   I checked and the back end site and the site is still using the self signed certificate. 

    I verified the new root certificate from my new enterprise CA was installed on my test Windows 10 workstation.  I ran Outlook and received the same error.

    Joel

    Wednesday, October 2, 2019 7:15 PM
  • Manu,

    As you suggested I ran the command Get-OrganizationConfig and verified MapiHttpEnabled was set to true. 

    I check the site's https binding on both the Default Web Site and Exchange Back End. Originally both sites were using the self sign certificated which is created during the install of Exchange.   As this issue might be caused by certificate miss match I installed an enterprise CA on my lab DC.  In a single certificate request I added the DNS names for autodiscover, outlook and the FQDN of the server.  From that request I created a valid certificate from my enterprise CA and assigned that certificate to the Default Website/Frontend.   I checked and the back end site and the site is still using the self signed certificate. 

    I verified the new root certificate from my new enterprise CA was installed on my test Windows 10 workstation.  I ran Outlook and received the same error.

    Joel

    Hi Joel,

    Please run the following command to test end-to-end Microsoft Outlook client connectivity in the Microsoft Exchange organization. 

    Test-OutlookConnectivity -RunFromServerId "<ServerId>" -ProbeIdentity OutlookMapiHttpSelfTestProbe

    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 9:59 AM
    Moderator
  • Manu,

    The test ran successfully with the following output.



    PSComputerName     : e2k16.lab.local
    RunspaceId         : 6c1bf4cf-73ff-4d02-8b61-7017546d32db
    PSShowComputerName : False
    Server             : e2k16.lab.local
    MonitorIdentity    : OutlookMapiHttp.Protocol\OutlookMapiHttpSelfTestProbe
    RequestId          : c9a4986b-d7b0-4553-a7ab-2f00858798d4
    ExecutionStartTime : 10/8/2019 11:27:18 PM
    ExecutionEndTime   : 10/8/2019 11:27:18 PM
    Error              : 
    Exception          : 
    PoisonedCount      : 0
    ExecutionId        : 18837784
    SampleValue        : 8.3482
    ExecutionContext   : 
    FailureContext     : 
    ExtensionXml       : 
    ResultType         : Succeeded
    RetryCount         : 0
    ResultName         : InvokeNow-OutlookMapiHttpSelfTestProbe
    IsNotified         : False
    ResultId           : 355165
    ServiceName        : InvokeNow
    StateAttribute1    : 
    StateAttribute2    : 
    StateAttribute3    : E2K16
    StateAttribute4    : E2K16
    StateAttribute5    : {06507A49-8E27-4460-8B80-1B0486DC9C72}
    StateAttribute6    : 0
    StateAttribute7    : 0
    StateAttribute8    : 0
    StateAttribute9    : 0
    StateAttribute10   : 0
    StateAttribute11   : 
    StateAttribute12   : 
    StateAttribute13   : VgEAVAdXaW5kb3dzQwBBCEtlcmJlcm9zTBdDQ1xIZWFsdGhNYWlsYm94YzJkOTk5M1UtUy0xLTUtMjEtMzI0NDM3MDkxNC0xMj
                         Q4NjIyMzItMjI2NzMzNDkxMC0xMTMyRwcAAAAHAAAALFMtMS01LTIxLTMyNDQzNzA5MTQtMTI0ODYyMjMyLTIyNjczMzQ5MTAt
                         NTEzBwAAAAdTLTEtMS0wBwAAAAdTLTEtNS0yBwAAAAhTLTEtNS0xMQcAAAAIUy0xLTUtMTUHAADAEVMtMS01LTUtMC02MDcxMj
                         YzBwAAAAhTLTEtMTgtMkUAAAAA
    StateAttribute14   : 
    StateAttribute15   : 
    StateAttribute16   : 0
    StateAttribute17   : 0
    StateAttribute18   : 0
    StateAttribute19   : 0
    StateAttribute20   : 16
    StateAttribute21   : /o=Lab/ou=Exchange Administrative Group 
                         (FYDIBOHF23SPDLT)/cn=Recipients/cn=3b3ba3ff06c343afa24f52f1cd78218f-HealthM
    StateAttribute22   : 
    StateAttribute23   : http://e2k16.lab.local:81/rpc/rpcproxy.dll?e2k16.cc.canisius.edu:6001
    StateAttribute24   : 
    StateAttribute25   : [2]10/8/2019 7:27:18 PM  RpcProxy connectivity verification; [5]10/8/2019 7:27:18 PM  Dummy 
                         verification.; 
    Identity           : c6485de8c2b1493e8bdf5b4c14656b74
    IsValid            : True
    ObjectState        : New



    Tuesday, October 8, 2019 11:29 PM
  • Hello,

    if you go to this url : https://e2k16.lab.local/owa

    do you have a certificate error ?

    Olivier.

    Thursday, October 10, 2019 7:46 AM
  • Manu,

    The test ran successfully with the following output.



    PSComputerName     : e2k16.lab.local
    RunspaceId         : 6c1bf4cf-73ff-4d02-8b61-7017546d32db
    PSShowComputerName : False
    Server             : e2k16.lab.local
    MonitorIdentity    : OutlookMapiHttp.Protocol\OutlookMapiHttpSelfTestProbe
    RequestId          : c9a4986b-d7b0-4553-a7ab-2f00858798d4
    ExecutionStartTime : 10/8/2019 11:27:18 PM
    ExecutionEndTime   : 10/8/2019 11:27:18 PM
    Error              : 
    Exception          : 
    PoisonedCount      : 0
    ExecutionId        : 18837784
    SampleValue        : 8.3482
    ExecutionContext   : 
    FailureContext     : 
    ExtensionXml       : 
    ResultType         : Succeeded
    RetryCount         : 0
    ResultName         : InvokeNow-OutlookMapiHttpSelfTestProbe
    IsNotified         : False
    ResultId           : 355165
    ServiceName        : InvokeNow
    StateAttribute1    : 
    StateAttribute2    : 
    StateAttribute3    : E2K16
    StateAttribute4    : E2K16
    StateAttribute5    : {06507A49-8E27-4460-8B80-1B0486DC9C72}
    StateAttribute6    : 0
    StateAttribute7    : 0
    StateAttribute8    : 0
    StateAttribute9    : 0
    StateAttribute10   : 0
    StateAttribute11   : 
    StateAttribute12   : 
    StateAttribute13   : VgEAVAdXaW5kb3dzQwBBCEtlcmJlcm9zTBdDQ1xIZWFsdGhNYWlsYm94YzJkOTk5M1UtUy0xLTUtMjEtMzI0NDM3MDkxNC0xMj
                         Q4NjIyMzItMjI2NzMzNDkxMC0xMTMyRwcAAAAHAAAALFMtMS01LTIxLTMyNDQzNzA5MTQtMTI0ODYyMjMyLTIyNjczMzQ5MTAt
                         NTEzBwAAAAdTLTEtMS0wBwAAAAdTLTEtNS0yBwAAAAhTLTEtNS0xMQcAAAAIUy0xLTUtMTUHAADAEVMtMS01LTUtMC02MDcxMj
                         YzBwAAAAhTLTEtMTgtMkUAAAAA
    StateAttribute14   : 
    StateAttribute15   : 
    StateAttribute16   : 0
    StateAttribute17   : 0
    StateAttribute18   : 0
    StateAttribute19   : 0
    StateAttribute20   : 16
    StateAttribute21   : /o=Lab/ou=Exchange Administrative Group 
                         (FYDIBOHF23SPDLT)/cn=Recipients/cn=3b3ba3ff06c343afa24f52f1cd78218f-HealthM
    StateAttribute22   : 
    StateAttribute23   : http://e2k16.lab.local:81/rpc/rpcproxy.dll?e2k16.cc.canisius.edu:6001
    StateAttribute24   : 
    StateAttribute25   : [2]10/8/2019 7:27:18 PM  RpcProxy connectivity verification; [5]10/8/2019 7:27:18 PM  Dummy 
                         verification.; 
    Identity           : c6485de8c2b1493e8bdf5b4c14656b74
    IsValid            : True
    ObjectState        : New



    OK, could you share some details of your IIS log?

    "Looking at the IIS logs I can see the workstation connecting to the autodiscover virtual directory endpoint but no other connections to the other Exchange virtual directories endpoints are made."

    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.

    Thursday, October 10, 2019 8:48 AM
    Moderator