It is common practice to keep your server up to date. I came across this error while updating my Exchange Server 2007 to the next service pack. I found many different methods to fix this problem on the internet but none of them worked.

Below was the error message I received when trying to visit the website.

Outlook Web Access did not initialize. An event has been logged so that the system administrator can resolve the issue. Please contact technical support for your organization.
Outlook Web Access was unable to access the Active Directory configuration settings for virtual directory “OWA” under Web site “owa”.

Request
Url: https://[OWA URL]:443/OWA/auth/error.aspx?replaceCurrent=1&url=https%3a%2f%2f[OWA URL]%2fOWA%2f
User host address: [Client IP Address]

Exception
Exception type: Microsoft.Exchange.Clients.Owa.Core.OwaInvalidConfigurationException
Exception message: Outlook Web Access was unable to access the Active Directory configuration settings for virtual directory “OWA” under Web site “owa”.

Call stack
Microsoft.Exchange.Clients.Owa.Core.OwaConfigurationManager.CreateAndLoadConfigurationManager()
Microsoft.Exchange.Clients.Owa.Core.Globals.InitializeApplication()
Microsoft.Exchange.Clients.Owa.Core.Global.ExecuteApplicationStart(Object sender, EventArgs e)

Inner Exception
Exception type: Microsoft.Exchange.Clients.Owa.Core.OwaInvalidConfigurationException
Exception message: Outlook Web Access was unable to access the Active Directory configuration settings for virtual directory “OWA” under Web site “owa”.

Call stack
Microsoft.Exchange.Clients.Owa.Core.Configuration..ctor(ADSystemConfigurationSession session, String virtualDirectory, String webSiteName, ADObjectId distinguishedName, Boolean isPhoneticSupportEnabled)
Microsoft.Exchange.Clients.Owa.Core.OwaConfigurationManager.LoadConfiguration()
Microsoft.Exchange.Clients.Owa.Core.OwaConfigurationManager.CreateAndLoadConfigurationManager()

After attempting many different lines and lines of PowerShell commands that did not work I came across the best way to fix this problem. The fix I found was to remove all virtual directories under the OWA and recreating them using these commands from PowerShell interface:

Remove-OwaVirtualDirectory “owa (Default Web Site)”
***(Default Web Site) may depend on what your directory name is. To find out what the correct directory names are use this the command: Get-OwaVirtualDirectory
New-OwaVirtualDirectory -WebSiteName “owa”

This re-synced the OWA Virtual Directory to the Active Directory and allowed OWA to be accessible again.

– Harry Caskey