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When you install a Exchange 2007 or 2010 client access server and using outlook 2007 or 2010. You will get a autodiscover error by default. Also connect with outlook webaccess or web app you get a certificate error.

To solve this problem you will have to import the certificate on all computers. Another way is to buy a trusted third party certificate. In most cases this will be a SAN / UCC certificate so you can use multiple names on the certificate, webmail.domain.name, autodiscover.domain.name, servername.domain.name and for a transition legacy.domain.name.

But after you request and installed the certificate you still get a autodiscover or certificate error.

Possible solution: you will have to change some autodiscover and client access setting, I will describe the wat to check and change the settings with the Exchange management shell. Some settings can also be changed by GUI.

Check the AutoDiscoverServiceInternalUri with the following command: Get-ClientAccessServer |ft Identity,AutoDiscoverServiceInternalUri
To change the setting: Set-ClientAccessServer -Identity “SERVERNAME” -AutoDiscoverServiceInternalUri “https://url.domain.name/autodiscover/autodiscover.xml”

For the next options you can set for both internal and external a different url. But you can choose to use same url for both in that case you will have to setup your internal and external dns right.

Check the AutodiscoverVirtualDirectory Get-AutodiscoverVirtualDirectory |ft internalurl,externalurl
To change the settings:
Set-AutodiscoverVirtualDirectory -Identity ‘SERVERNAME\Autodiscover (Default Web site)’ -ExternalUrl https://externalurl.domain.name/Autodiscover/Autodiscover.xml’
Set-AutodiscoverVirtualDirectory -Identity ‘SERVERNAME\Autodiscover (Default Web site)’ -InternalUrl ‘https://internalurl.domain.name/Autodiscover/Autodiscover.xml’

Check the WebServicesVirtualDirectory InternalUrl and ExternalUrl Get-WebServicesVirtualDirectory |ft internalurl,externalurl
To change the settings:
Set-WebServicesVirtualDirectory -Identity ‘SERVERNAME\EWS (Default Web site)’ -ExternalUrl ‘https://externalurl.domain.name/EWS/Exchange.asmx’
Set-WebServicesVirtualDirectory -Identity ‘SERVERNAME\EWS (Default Web site)’ -InternalUrl ‘https://internalurl.domain.name/EWS/Exchange.asmx’

You will have to do the same thing for all the next option. If you don’t use one of these options you can consider skipping the setting.

Get-OabVirtualDirectory |ft internalurl,externalurl
Set-OabVirtualDirectory -Identity “SERVERNAME\OAB (Default Web site)” -InternalUrl ‘https://internalurl.domain.name/OAB’
Set-OabVirtualDirectory -Identity “SERVERNAME\OAB (Default Web site)” -ExternalUrl ‘https://externalurl.domain.name/OAB’

Get-UMVirtualDirectory |ft internalurl,externalurl
Set-UMVirtualDirectory -Identity “SERVERNAME\UnifiedMessaging (Default Web site)” -InternalUrl ‘https://internalurl.domain.name/UnifiedMessaging/Service.asmx’
Set-UMVirtualDirectory -Identity “SERVERNAME\UnifiedMessaging (Default Web site)” -ExternalUrl ‘https://externalurl.domain.name/UnifiedMessaging/Service.asmx’

Note: when you using SBS 2008 you should replace (Default Web site) by (SBS Web Applications)

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