Over the last few days, I’ve been having problems connecting to Microsoft Update from a newly built Windows Server 2003 R2 server. Whilst searching for updates, it’s was hanging (green progress bar pulsing across the screen) before eventually reporting:

[Error number: 0x80244023]

The website has encountered a problem and cannot display the page you are trying to view. The options provided below might help you solve the problem.

For self-help options:

Frequently Asked Questions
Find Solutions
Windows Update Newsgroup

For assisted support options:

Microsoft Online Assisted Support (no-cost for Windows Update issues)

Sadly, Microsoft’s Online Assisted Support didn’t do much assisting – it only pointed me back to the knowledge base, newsgroups, or paid incident support but the problem did go away all by itself (yes, really)!

In the meantime, I’d asked for help on the Microsoft Windows Update discussion group and a really helpful MVP called TaurArian replied pointing me in the direction of the MSDN reference for Windows Update agent networking error codes. Useful stuff – and it turns out that 80244023 is WU_E_PT_HTTP_STATUS_GATEWAY_TIMEOUT – i.e. proxy server problems (and probably the reason why the problem seemed to cure itself).