Today I had issues patching a Windows Server 2008 R2 server at one of my clients. Windows Update provided me with the following error message:
A error occurred while checking for new updates for your computer. Error Code 80244018
This error code is generated when a computer has issues connecting to the Windows Update server. My customer used Threat Management Gateway as a firewall solution. After reviewing the firewall rules there was a rule which prevented access to Microsoft Windows Update servers.