There are several reasons why CRM for Outlook won't connect to the server - wrong credentials, excessive temporary files on the computer, corrupted client or other issues with MS Office. These could apply on any of the supported Windows versions, but...before you go through trying to fix any/all of that, there might be another very simple cause. In Windows 8, there is an issue with the Windows Identity Foundation 3.5 feature component. On Windows 8, with CRM for Outlook at Rollup 10 or earlier, this component is not active, by default and without it CRM for Outlook will fail to connect to the CRM server.
When inspecting the client configuration log, the following error information is found for both symptoms:
14:12:40| Error| Error connecting to URL: https://crm.contoso.com:444/XRMServices/2011/Discovery.svc Exception: System.IO.FileNotFoundException: Could not load file or assembly 'Microsoft.IdentityModel, Version=18.104.22.168, Culture=neutral, PublicKeyToken=31bf3856ad364e35' or one of its dependencies. The system cannot find the file specified.
File name: 'Microsoft.IdentityModel, Version=22.214.171.124, Culture=neutral, PublicKeyToken=31bf3856ad364e35'
at Microsoft.Crm.Outlook.ClientAuth.ClientAuthProvidersFactory`1.SignIn(Uri endPoint, Credential credentials, AuthUIMode uiMode, IClientOrganizationContext context, Form parentWindow, Boolean retryOnError)
at Microsoft.Crm.Application.Outlook.Config.DeploymentsInfo.DeploymentInfo.LoadOrganizations(AuthUIMode uiMode, Form parentWindow, Credential credentials)
at Microsoft.Crm.Application.Outlook.Config.DeploymentsInfo.InternalLoadOrganizations(OrganizationDetailCollection orgs, AuthUIMode uiMode, Form parentWindow)
Reference article KB2727137 http://support.microsoft.com/kb/2727137
The problem has been fixed in CRM 2011 Rollup 11, but if you are at an earlier Rollup version, you need to do the following to manually enable the Windows Identity Foundation 3.5 component:
1. In the Start menu, right-click, and then select All Apps
2. Under the Windows System group, select Control Panel
3. Click on Programs, and then click Programs and Features
4. In the left menu, click Turn Windows features on or off
5. Scroll through the list to find Windows Identity Foundation 3.5 - enable this feature.
Reboot your computer. Try running through the CRM configuration wizard again.