Outlook is pulling incorrent settings from exchange 2010

cbdrako99
cbdrako99 used Ask the Experts™
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We have the external entries set in exchange for remote.COMPANY.com but when machines travel from inside the network to outside, Outlook changes the remote.company.com to mail.company.com. We have verified that the external settings all specify remote.company.com and the auto discovery looks fine. I am attaching the AutoDiscover file.

 
<Autodiscover xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" xmlns:xsd="http://www.w3.org/2001/XMLSchema" xmlns="http://schemas.microsoft.com/exchange/autodiscover/responseschema/2006">
<Response xmlns="http://schemas.microsoft.com/exchange/autodiscover/outlook/responseschema/2006a">
<User>
<DisplayName>Test User</DisplayName>
<LegacyDN>/o=COMPANY/ou=Exchange Administrative Group (FYDIBOHF23SPDLT)/cn=Recipients/cn=TestUser</LegacyDN>
<DeploymentId>58a0710e-1afc-4a99-b1a4-c12b87b8580a</DeploymentId>
</User>
<Account>
<AccountType>email</AccountType>
<Action>settings</Action>
<Protocol>
<Type>EXCH</Type>
<Server>SERVER.COMPANY.local</Server>
<ServerDN>/o=COMPANY/ou=Exchange Administrative Group (FYDIBOHF23SPDLT)/cn=Configuration/cn=Servers/cn=SERVER</ServerDN>
<ServerVersion>720180F0</ServerVersion>
<MdbDN>/o=COMPANY/ou=Exchange Administrative Group (FYDIBOHF23SPDLT)/cn=Configuration/cn=Servers/cn=SERVER/cn=Microsoft Private MDB</MdbDN>
<ASUrl>https://remote.COMPANYinc.com/EWS/Exchange.asmx</ASUrl>
<OOFUrl>https://remote.COMPANYinc.com/EWS/Exchange.asmx</OOFUrl>
<OABUrl>https://remote.COMPANYinc.com/OAB/5030dcac-1765-4469-abde-4a191ef3dd95/</OABUrl>
<UMUrl>https://remote.COMPANYinc.com/UnifiedMessaging/Service.asmx</UMUrl>
<Port>0</Port>
<DirectoryPort>0</DirectoryPort>
<ReferralPort>0</ReferralPort>
<PublicFolderServer>SERVER.COMPANY.local</PublicFolderServer>
<AD>SERVER.COMPANY.local</AD>
<EwsUrl>https://remote.COMPANYinc.com/EWS/Exchange.asmx</EwsUrl>
</Protocol>
<Protocol>
<Type>EXPR</Type>
<Server>mail.COMPANYinc.com</Server>
<ASUrl>https://remote.COMPANYinc.com/EWS/Exchange.asmx</ASUrl>
<OOFUrl>https://remote.COMPANYinc.com/EWS/Exchange.asmx</OOFUrl>
<OABUrl>https://remote.COMPANYinc.com/OAB/5030dcac-1765-4469-abde-4a191ef3dd95/</OABUrl>
<UMUrl>https://remote.COMPANYinc.com/UnifiedMessaging/Service.asmx</UMUrl>
<Port>0</Port>
<DirectoryPort>0</DirectoryPort>
<ReferralPort>0</ReferralPort>
<EwsUrl>https://remote.COMPANYinc.com/EWS/Exchange.asmx</EwsUrl>
</Protocol>
<Protocol>
<Type>WEB</Type>
<Port>0</Port>
<DirectoryPort>0</DirectoryPort>
<ReferralPort>0</ReferralPort>
<External>
<OWAUrl AuthenticationMethod="Fba">https://remote.COMPANYinc.com/owa/</OWAUrl>
<Protocol>
<Type>EXPR</Type>
<ASUrl>https://remote.COMPANYinc.com/EWS/Exchange.asmx</ASUrl>
</Protocol>
</External>
<Internal>
<OWAUrl AuthenticationMethod="Basic, Fba">https://remote.COMPANYinc.com/owa/</OWAUrl>
<Protocol>
<Type>EXCH</Type>
<ASUrl>https://remote.COMPANYinc.com/EWS/Exchange.asmx</ASUrl>
</Protocol>
</Internal>
</Protocol>
</Account>
</Response>
</Autodiscover>

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Commented:
Have you tried testing with www.testexchangeconnectivity.com and see what errors, if any, it shows?
Run the following and post:

get-owavirtualdirectory | fl name,*ternal*
get-oabvirtualdirectory | fl name,*ternal*
get-webservicesvirtualdirectory | fl name,*ternal*
get-clientaccessserver | fl name,*ternal*
AkhaterSolutions Architect

Commented:
your issue is most probably related to the outlook provider

issue a get-outlookprovider  and check the EXCh value if it is false change it using

set-outlookprovider exch -server remote.company.com

Author

Commented:
We have tried www.testexchangeconnectivity.com. Here is the output requested:


[PS] C:\Windows\System32>get-owavirtualdirectory | fl name,*ternal*


Name                                    : owa (SBS Web Applications)
RemoteDocumentsInternalDomainSuffixList : {}
InternalAuthenticationMethods           : {Basic, Fba}
InternalUrl                             : https://remote.COMPANY.com/owa/
ExternalUrl                             : https://remote.COMPANY.com/owa/
ExternalAuthenticationMethods           : {Fba}

Name                                    : Exadmin (SBS Web Applications)
RemoteDocumentsInternalDomainSuffixList :
InternalAuthenticationMethods           : {Basic, Ntlm, WindowsIntegrated}
InternalUrl                             :
ExternalUrl                             :
ExternalAuthenticationMethods           : {Fba}

Name                                    : Exchange (SBS Web Applications)
RemoteDocumentsInternalDomainSuffixList :
InternalAuthenticationMethods           : {Basic, Ntlm, WindowsIntegrated}
InternalUrl                             :
ExternalUrl                             :
ExternalAuthenticationMethods           : {Fba}

Name                                    : Exchweb (SBS Web Applications)
RemoteDocumentsInternalDomainSuffixList :
InternalAuthenticationMethods           : {Basic, Ntlm, WindowsIntegrated}
InternalUrl                             :
ExternalUrl                             :
ExternalAuthenticationMethods           : {Fba}

Name                                    : Public (SBS Web Applications)
RemoteDocumentsInternalDomainSuffixList :
InternalAuthenticationMethods           : {Basic, Ntlm, WindowsIntegrated}
InternalUrl                             :
ExternalUrl                             :
ExternalAuthenticationMethods           : {Fba}



[PS] C:\Windows\System32>
[PS] C:\Windows\System32>get-owavirtualdirectory | fl name,*ternal*


Name                                    : owa (SBS Web Applications)
RemoteDocumentsInternalDomainSuffixList : {}
InternalAuthenticationMethods           : {Basic, Fba}
InternalUrl                             : https://remote.COMPANY.com/owa/
ExternalUrl                             : https://remote.COMPANY.com/owa/
ExternalAuthenticationMethods           : {Fba}

Name                                    : Exadmin (SBS Web Applications)
RemoteDocumentsInternalDomainSuffixList :
InternalAuthenticationMethods           : {Basic, Ntlm, WindowsIntegrated}
InternalUrl                             :
ExternalUrl                             :
ExternalAuthenticationMethods           : {Fba}

Name                                    : Exchange (SBS Web Applications)
RemoteDocumentsInternalDomainSuffixList :
InternalAuthenticationMethods           : {Basic, Ntlm, WindowsIntegrated}
InternalUrl                             :
ExternalUrl                             :
ExternalAuthenticationMethods           : {Fba}

Name                                    : Exchweb (SBS Web Applications)
RemoteDocumentsInternalDomainSuffixList :
InternalAuthenticationMethods           : {Basic, Ntlm, WindowsIntegrated}
InternalUrl                             :
ExternalUrl                             :
ExternalAuthenticationMethods           : {Fba}

Name                                    : Public (SBS Web Applications)
RemoteDocumentsInternalDomainSuffixList :
InternalAuthenticationMethods           : {Basic, Ntlm, WindowsIntegrated}
InternalUrl                             :
ExternalUrl                             :
ExternalAuthenticationMethods           : {Fba}



[PS] C:\Windows\System32>get-oabvirtualdirectory | fl name,*ternal*


Name                          : OAB (SBS Web Applications)
InternalUrl                   : https://remote.COMPANY.com/OAB
InternalAuthenticationMethods : {WindowsIntegrated}
ExternalUrl                   : https://remote.COMPANY.com/OAB
ExternalAuthenticationMethods : {WindowsIntegrated}



[PS] C:\Windows\System32>get-webservicesvirtualdirectory | fl name,*ternal*


Name                          : EWS (SBS Web Applications)
InternalNLBBypassUrl          : https://SERVER.COMPANY.local/EWS/Exchange.asmx
InternalAuthenticationMethods : {Basic, Ntlm, WindowsIntegrated}
ExternalAuthenticationMethods : {Basic, Ntlm, WindowsIntegrated}
InternalUrl                   : https://remote.COMPANY.com/EWS/Exchange.asmx
ExternalUrl                   : https://remote.COMPANY.com/EWS/Exchange.asmx



[PS] C:\Windows\System32>get-clientaccessserver | fl name,*ternal*


Name                           : SERVER
AutoDiscoverServiceInternalUri : https://remote.COMPANY.com/Autodiscover/Autodiscover.xml



[PS] C:\Windows\System32>

[PS] C:\Windows\System32>get-outlookprovider

Name                Server              CertPrincipalName   TTL
----                ------              -----------------   ---
EXCH                                                        1
EXPR                mail.company...                         1
WEB                                                         1


[PS] C:\Windows\System32>

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Everything looks OK except your Outlook Provider as it is set to mail.company.com.  This is an easy fix and only differs based on which certificate type you are using.

Single name or SAN certificate:
Set-OutlookProvider -Identity EXPR -Server remote.company.com

Wildcard certificate:
Set-OutlookProvider -Identity EXPR -Server remote.company.com -CertPrincipalName *.company.com

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