Essential Business Server 2008 (EBS 2008) has in my experience been a very stable environment, but I have struck a few interesting issues. Here are solutions to some of the issues I have encountered:

Outlook prompts for authentication every few minutes

I found the solution to this was to change authentication on “AutoDiscover” in IIS on the Messaging Server. Details can be found on the Essential Business Server Team Blog

.NET Framework 3.5 will not install

To resolve installation errors with .NET 3.5 I downloaded the “.NET Cleanup tool” and removed all copies of .NET 3.5. I then restarted the server with the issue and reinstalled .NET 3.5 + service pack 1 sucessfully.

System Centre Essentials reporting stops after applying hotfix KB948109

Microsoft have released Hotfix KB957755 to resolve this issue.