Your issue is likely TLS issues
https://www.microsoft.com/security/blog/2017/07/20/tls-1-2-support-added-to-windows-server-2008/
http://www.catalog.update.microsoft.com/Search.aspx?q=KB4019276
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I am trying to update a new virtual Windows 2008 32 bit server. Every time I go to Windows update the new server with all Windows 2008 patches, I get the error "windows update error 80244019", any suggestion? It was working fine few weeks ago.
What is TLS:
https://www.cloudflare.com/en-ca/learning/ssl/transport-layer-security-tls/
TLS1.2 is what you should be using. 1.0, 1.1 are deprecated, and 1.3 is not widely used.
While you're at it, you'll want to update for SHA256 signing as SHA-1 is deprecated too
Old OS note: Windows Server 2008 and 2008 R2 are NO LONGER receiving security updates by Microsoft as they went out of support on January 14, 2020. You should be looking to update those systems, and not use 2008.
I'd verify system and servicing health by running;
sfc /scannow
also system update readiness tool
https://support.microsoft.com/en-us/kb/947821
Then check for errors in;
%SYSTEMROOT%\Logs\CBS\CheckSUR.log
--please don't forget to Accept as answer if the reply is helpful--
The TLS 1.2 patches fixed this error for me. Server 2008 was the Windows Vista equivalent. It's simply amazing that TLS 1.2 was even added to this EOL leftover.
I've tried evertything seen here but it didn't work on my Windows Server 2008 SP2. The issue is related with the deprecation of SHA1 cypher.
To fix this issue i've installed KB4474419 (without WSUS and non joined domain pc). If you use WSUS KB4484071.
More information: https://support.microsoft.com/en-us/help/4569557/windows-update-sha-1-based-endpoints-discontinued