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Windows update fails for Windows 2003 server

I have a Windows 2003 server behind Astaro firewall, and I cannot access Windows update. The HTTP proxy is operating in transparent mode, and the message from Astaro after activating "Review and install updates" from the Windows Update page is:
Please check the spelling of your URL
Make sure that your proxy settings are in order
The following lines may provide some additional information to the cause of the failure
unparsable request line ' '

Any ideas on what's wrong?

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0 VelvetFog over 20 years ago

[ QUOTE ]
The HTTP proxy is operating in transparent mode

[/ QUOTE ]That's likely to be your problem.
Try it with the HTTP proxy in normal (non-transparent) mode instead.
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0 BPC over 20 years ago

I had the same problem, try using ssl instead

https://windowsupdate.microsoft.com

That should do the trick, atleast it did for me.
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0 John Agnew over 20 years ago in reply to BPC

Which version of ASL are you using ? I had this problem with 5.02x - an upgrade to 5.100 solved it.

John
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0 LegalEdge over 20 years ago in reply to John Agnew

I have the exact same problem on 5.100 with the proxy in user auth mode. It's defintely something to do with the http proxy, turning it off and adding packet filter rules to pass http and https traffic works fine. Have not experienced problems with any other web sites that I'm aware of or that my users have beat me up on. A pain in the butt though since Windows Update is kinda necessary for the M$ world!
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0 SalishSwede over 20 years ago

Burried in the details of the HTTP Proxy manual it indicates that the transparent proxy does not support HTTPS nor FTP (Normal Mode Does). So if your packet filter rules allow HTTPS, I things should work. At least they work for me.

This is how I have things set up:
Win2003 Server + misc clients
behind Astaro 5.102

The following services work fine:
Web-based Windows Update
Windows Update Services beta
Software Update Services
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0 William Warren over 20 years ago in reply to SalishSwede

I run my proxy in transparent without issues on WU.
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0 Tim F over 20 years ago in reply to SalishSwede

I have the same problem, running asl 5.100 http proxy in auth mode and cannot run Windows Update. Turned off Proxy and created rules and works fine.
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0 Sascha_Paris over 20 years ago in reply to Tim F

I HAD the problem with ASL 5.100. Update to 5.101 or 5.102 solved the problem...I do not remember exactly. However...this failure happened only in transparent proxy mode, but works now fine [;)]

After update you'll maybe have to clear the http proxy cache and / or the clients http cache (Internet Explorer)...
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