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Exchange 2007/2010 Web services and Autodiscover Ultimate Troubleshooting Guide

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Hi, during my online activities I can see that Exchange 2007/2010 web services are causing a lot of issues to people, and lots are suffering from it.
I decided to put this ultimate guide to spare the hustle and allow smoother and nicer web services experience.
Well, let us first list the directories that are used in the Exchange web service:
EWS is used for OOF, Scheduling assistance and free+busy Lookup.
OAB provides offline address book download services for client.
Autodiscover is used to provide users with autodiscover service.
EAS provides ActiveSync services to Windows Mobile based devices.
OWA provides outlook web access for users.
ECP provides Exchange control panel feature for Exchange 2010 users only.
Issues that might be resolved using the troubleshooting steps here:
You cannot set the OOF using outlook client, you receive the server not available error.
You cannot view free/busy information for other users.
You cannot use scheduling assistance, also you might receive not free/busy information data retrieved.
You cannot download Offline Address book errors.
You cannot use autodiscover externally.
Certificate mismatch error in autodiscover, users prompted to trust certificate in outlook 2007/2010.
I will update this post to include all of the errors that I face and solve in my work or on EE to help experts all over EE to quickly solve their issues.
First let us start by the configuration required post Exchange 2007/2010 installation for the above to work correctly:
Configure External and Internal URLs for OWS, ref: http://technet.microsoft.com/en-us/library/bb691323(EXCHG.80).aspx 
You have to configure the internal URL to be the server name in case you have multiple servers in NLB.
External URL will be the URL used by users to access webmail e.g. https://mail.domain.com/owa
Mail.domain.com in multiple CAS servers will be the NLB FQDN.
Configure External and Internal URLs for OAB, ref: http://technet.microsoft.com/en-us/library/bb123710.aspx
This will point if multiple CAS servers are used then this will point to NLB FQDN.
If single server used this will point to the internal server FQDN in the internal URL, and the mail.domain.com which is used by webmail users.
Configure the autodiscover internal URL:
You will use the powershell cmdlet : Set-ClientAccessServer –Identity <CAS Server Name> -AutoDiscoverServiceInternalUri: <Internal URL>, this FQDN must match the URL included in the certificate.
If you cannot use autodiscover.domain.com internally (you have a domain name of domain.local and you must use it), you will get a certificate miss match error, you will have to include the internal name in the certificate if you purchase an external certificate.
If you have multiple CAS in NLB this will be the NLB FQDN.
You cannot set autodiscover external URL since outlook will try to access https://autodiscover.domain.com/autodiscover/autodiscover.xml, this behavior is by design and cannot be changed.
Autodiscover.domain.com must be included in the certificate that you assign to IIS if you purchasing a certificate externally from 3rd party provider.
Configure EAS internal and External URLs, ref: http://technet.microsoft.com/en-us/library/bb629533(EXCHG.80).aspx
This URL will point to the NLB FQDN internally
This IRL will point to NLB FQDN Externally.
Configure the EWS (which provides availability, OOF) internal and external URLs
You can set the internal FQDN and External FQDN using: get-webservicesvirtualdirectory | Set-WebServicesVirtualDirectory  –InternalUrl: https://url.domain.local/EWS/Exchange.asmx –ExternalURl: https://url.domain.com/EWS/Exchange.asmx
after all of the above settings you have to take into considerations the following note:
All of the above uses https connection, so SSL certificate must be configured and assigned to IIS on the CAS servers.
Since all of the above uses https, if you have a proxy traffic might be affected.
Make sure that clients can access the URL internally and externally, you can do that by going to the above URL using IE or Firefox and validate that you can access them.
For some people after doing the above configuration you still receive some errors so make sure of the following:
IIS is started.
OWA application pool, OAB application pool and EWS application pool are running and started with no errors
If you receive authentication error, error 500 service not available, error 400 login time out, or unspecified error you will need to rebuild your virtual directories. You can do that as following:
For OWA:
Get-owavirtualdirectory | remove-owavirtualdirectory
You can repeat this step for EWS (webservicesdirectory), OAB (OABvirtualdirectory) and autodiscover(autodiscovervirtualdirectory)
You will have to note that you will need to re-configure any customizations you made to OWA after removing and deleting it, also you will have to redo any internal and external URL configuration you have did in the past

Hope that I helped you in this post, the post will be updated to include all of the issues we solve to give you the smoothest Exchange experience.
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LVL 33

Author Comment

Just a quick correction:
the autodiscover inernal FQDN must be set using the following:
Set-ClientAccessServer -Identity CASServer -AutoDiscoverServiceInternalUri https://mail.domain.com/Autodiscover/Autodiscover.xml
so the URI must be the full address  https://mail.domain.com/Autodiscover/Autodiscover.xml
LVL 33

Author Comment

I found that you might get the following error also:
"Your Out of Office settings cannot be displayed, because the server is currently unavailable. Try again Later."
 please make sure that you have Anonymous authentication and windows authentication enabled on the EWS virtual directory
LVL 33

Author Comment

you might get
"Your Out of Office settings cannot be displayed, because the server is currently unavailable. Try again Later."
or you cannot set the OOF and get unspecified error
the solution:
mail sure The service Mailbox Assistant is running on the mailbox servers.  for some virtual servers or mailbox servers with low amount of memory set the service to delayed restart and restart the servers
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Expert Comment

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