HTTP Error 56: Failure when receiving data from the peer: Received HTTP code 400 from proxy after CONNECT : Trying to Configure Bigfix Proxy

I am attempting to set up a Windows Server 2022 as my Proxy server for patches. I have set the settings up with the besadmin tool and the set proxy settings. I have verified the FW is allowing traffic through port 80 and I can telnet to the proxy server from the bigfix server and vice versa.

When I review BESAdminDebugOut I see Error 28 and Error 404 not found.

Tue, 28 Jun 2022 15:05:50 +0100 – 8320 – An error occurred while testing the connection: HTTP Error 28: Timeout was reached: Connection timeout after 10014 ms
Tue, 28 Jun 2022 15:06:25 +0100 – 8320 – An error occurred while testing the connection: HTTP Error 28: Timeout was reached: Connection timeout after 10005 ms
Tue, 28 Jun 2022 15:07:41 +0100 – 8320 – An error occurred while testing the connection: HTTP Error 28: Timeout was reached: Connection timeout after 10014 ms
Tue, 28 Jun 2022 15:08:08 +0100 – 8320 – An error occurred while testing the connection: HTTP Error 28: Timeout was reached: Connection timeout after 10001 ms
Tue, 28 Jun 2022 15:31:22 +0100 – 8320 – An error occurred while testing the connection: Unexpected HTTP response: 404 Not Found
Tue, 28 Jun 2022 15:31:38 +0100 – 8320 – An error occurred while testing the connection: Unexpected HTTP response: 404 Not Found
Tue, 28 Jun 2022 15:33:21 +0100 – 8320 – An error occurred while testing the connection: Unexpected HTTP response: 404 Not Found

If this is a new Proxy, I’d start by verifying that browser connections through the proxy work correctly.

On the proxy, the patch sites work through web browser like chrome and IE. I’ve also modified the settings on the BF server to connect through the host. It’s just whenever I try to connect through the patch sites or curl command from the BigFix server I get an error. I can’t tell what is blocking the connection.

“on the proxy” - do you mean from the proxy server itself? What proxy product are you using?
It’s not clear to me that whether you actually have a proxy product installed and running.

Sorry, I meant the proxy server. We don’t have any special proxy product software running, just what I have with Windows Server. Would I need to load any special proxy software to configure ?

On the BigFix server, I modified the settings in Internet Explorer through the options to use the proxy server that we set up.

Yes, additional software is needed to perform the proxy function.
What is your goal? Why are you trying to use a proxy?
By the sound of it’s you should just use BESAdmin to remove the proxy client configuration and let it use direct internet connections.