Hi, some of our users who are working externally are experiencing an odd issue with outlook when trying to access there emails / add there exchange account to outlook.

when adding a new account to outlook it asks for username and password, which it accepts fine, however on "Log on to server and send a test e-mail message" it requests a logon to a random server known as "Plymouth.footholds.net" not "mail.domain.com" as expected, this is not a server within our network or something that we control, no DNS settings point to this server, and no settings were changed prior to this issue occurring.

It is a server hosted by "vidahost", they provide us with web hosting for our website but nothing else, there is no reason for this to have found its way into the auto discovery configuration

does any1 have any suggestions on how to troubleshoot this, I cant find any trace of "Plymouth.footholds.net" in any of my auto discovery settings / DNS settings and auto discovery is functioning correctly on other systems such as Mozilla Thunderbird, seems to be an outlook issue.

Internally within the domain autodiscovery functions correctly and as expected, this only effects external users.

Many Thanks
Gordon

Hello

tip: try check your domain with https://testconnectivity.microsoft.com/

Yes I ran that test, forgot to mention in the original post, it all comes back green, no problems, also MX Toolbox shows no issues too.

Many Thanks

Gordon

Hello

tip: check wrong client host file
and check externalurls in exchange

Thanks for the reply,

yep checked the host files, there is no odd settings in there ( it affects multiple users who are external on different systems and my test system I have internal so I will rule out host files being an issue) however,

Get-AutodiscoveryVirtualDiectory | FL seems to returns fine (see Below),

and

Get-ClientAccessServer retuns the correct AutodiscoverServiceInternalURI

[PS] C:\Windows\system32>Get-AutodiscoverVirtualDirectory | fl

RunspaceId                      : d0ff3c24-b951-45ab-a079-f61a771cf54f
Name                            : Autodiscover (Default Web Site)
InternalAuthenticationMethods   : {Basic, Ntlm, WindowsIntegrated, WSSecurity, OAuth}
ExternalAuthenticationMethods   : {Basic, Ntlm, WindowsIntegrated, WSSecurity, OAuth}
LiveIdNegotiateAuthentication   : False
WSSecurityAuthentication        : True
LiveIdBasicAuthentication       : False
BasicAuthentication             : True
DigestAuthentication            : False
WindowsAuthentication           : True
OAuthAuthentication             : True
AdfsAuthentication              : False
MetabasePath                    : IIS://Exchange2013.InternalDomain.co.uk/W3SVC/1/ROOT/Autodiscover
Path                            : C:\Program Files\Microsoft\Exchange Server\V15\FrontEnd\HttpProxy\Autodiscover
ExtendedProtectionTokenChecking : None
ExtendedProtectionFlags         : {}
ExtendedProtectionSPNList       : {}
AdminDisplayVersion             : Version 15.0 (Build 712.24)
Server                          : EXCHANGE2013
InternalUrl                     :
ExternalUrl                     :
AdminDisplayName                :
ExchangeVersion                 : 0.10 (14.0.100.0)
DistinguishedName               : CN=Autodiscover (Default Web Site),CN=HTTP,CN=Protocols,CN=EXCHANGE2013,CN=Servers,CN=Exchange Administrative Group (FYDIBOHF23SPDLT),CN=Administrative Groups,CN=External Domain,CN=Microsoft Exchange,CN=Services,CN=Configuration,DC=InternalDomain,DC=co,DC=uk
Identity                        : EXCHANGE2013\Autodiscover (Default Web Site)
Guid                            : 067122c0-f992-45ae-96b5-f003d666bb53
ObjectCategory                  : InternalDomain.co.uk/Configuration/Schema/ms-Exch-Auto-Discover-Virtual-Directory
ObjectClass                     : {top, msExchVirtualDirectory, msExchAutoDiscoverVirtualDirectory}
WhenChanged                     : 10/10/2013 12:20:21
WhenCreated                     : 10/10/2013 12:20:16
WhenChangedUTC                  : 10/10/2013 11:20:21
WhenCreatedUTC                  : 10/10/2013 11:20:16
OrganizationId                  :
OriginatingServer               : DC1.InternalDomain.co.uk
IsValid                         : True
ObjectState                     : Changed

• Edited by BpdZenithLtd 19 hours 14 minutes ago

Can you run Get-OutlookAnywhere | fl name, *url*

yes I can run it, outlook anywhere functions fine to.

It Returned

[PS] C:\Windows\system32>Get-OutlookAnywhere| fl name, *url*
Name    : Rpc (Default Web Site)
XropUrl :

Many Thanks

Sorry... i gave you the wrong information i was looking for... 

Can you run get-outlookanywhere | fl server, *host*

I was just doing some CAS stuff and URL on my mind. apologies.

No problem, yea I can run that command it returns the expected External and internal hostnames for the Exchange server.

nothing out of the ordinary there.

Many Thanks

Gordon

Thanks for the reply,

yep checked the host files, there is no odd settings in there ( it affects multiple users who are external on different systems and my test system I have internal so I will rule out host files being an issue) however,

Get-AutodiscoveryVirtualDiectory | FL seems to returns fine (see Below),

and

Get-ClientAccessServer retuns the correct AutodiscoverServiceInternalURI

[PS] C:\Windows\system32>Get-AutodiscoverVirtualDirectory | fl

RunspaceId                      : d0ff3c24-b951-45ab-a079-f61a771cf54f
Name                            : Autodiscover (Default Web Site)
InternalAuthenticationMethods   : {Basic, Ntlm, WindowsIntegrated, WSSecurity, OAuth}
ExternalAuthenticationMethods   : {Basic, Ntlm, WindowsIntegrated, WSSecurity, OAuth}
LiveIdNegotiateAuthentication   : False
WSSecurityAuthentication        : True
LiveIdBasicAuthentication       : False
BasicAuthentication             : True
DigestAuthentication            : False
WindowsAuthentication           : True
OAuthAuthentication             : True
AdfsAuthentication              : False
MetabasePath                    : IIS://Exchange2013.InternalDomain.co.uk/W3SVC/1/ROOT/Autodiscover
Path                            : C:\Program Files\Microsoft\Exchange Server\V15\FrontEnd\HttpProxy\Autodiscover
ExtendedProtectionTokenChecking : None
ExtendedProtectionFlags         : {}
ExtendedProtectionSPNList       : {}
AdminDisplayVersion             : Version 15.0 (Build 712.24)
Server                          : EXCHANGE2013
InternalUrl                     :
ExternalUrl                     :
AdminDisplayName                :
ExchangeVersion                 : 0.10 (14.0.100.0)
DistinguishedName               : CN=Autodiscover (Default Web Site),CN=HTTP,CN=Protocols,CN=EXCHANGE2013,CN=Servers,CN=Exchange Administrative Group (FYDIBOHF23SPDLT),CN=Administrative Groups,CN=External Domain,CN=Microsoft Exchange,CN=Services,CN=Configuration,DC=InternalDomain,DC=co,DC=uk
Identity                        : EXCHANGE2013\Autodiscover (Default Web Site)
Guid                            : 067122c0-f992-45ae-96b5-f003d666bb53
ObjectCategory                  : InternalDomain.co.uk/Configuration/Schema/ms-Exch-Auto-Discover-Virtual-Directory
ObjectClass                     : {top, msExchVirtualDirectory, msExchAutoDiscoverVirtualDirectory}
WhenChanged                     : 10/10/2013 12:20:21
WhenCreated                     : 10/10/2013 12:20:16
WhenChangedUTC                  : 10/10/2013 11:20:21
WhenCreatedUTC                  : 10/10/2013 11:20:16
OrganizationId                  :
OriginatingServer               : DC1.InternalDomain.co.uk
IsValid                         : True
ObjectState                     : Changed

• Edited by BpdZenithLtd Wednesday, March 11, 2015 12:06 PM

what does autodiscover.domain.com resolve to externally? Is it the external ip of the vip on your load balancer?

looks like the issue was external to our network, as a I rasied a ticket with vidahost and they resolved the issue, still no idea what caused the problem sadly

• Proposed as answer by Hinte 18 hours 31 minutes ago