Problems with corporate proxy

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Karaoke

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Nov 23, 2018
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I'll start by apologizing that I am clearly not a professional sysadmin, so I have only a rudimentary working knowledge of unix-based systems.

I set up a FreeNAS 9.1 server awhile back without much of a hitch; computers on the LAN can connect without a problem, etc. At the time, I couldn't get outgoing email to work via gmail (error code 65; no route to host), which is clearly due to being behind a restrictive corporate firewall. I didn't have the energy to fix it at the time, and had been manually checking the NAS health, but that's obviously suboptimal, so I'm revisiting the issue. I haven't found anything in the forums that could help, so here I am. I've realized that this issue essentially blocks the server from accessing anything outside of the local network. The HTTP Proxy is set appropriately in the network gui (in the format: 'http://proxy.foo.bar:3128'), but this is clearly insufficient. As one might expect, I'm also unable to connect to the update server so cannot download an upgrade nor grab e.g. jail templates. I'm getting the following error attempting to access e.g. the update servers.

Host proxy.foo.bar:3128 returned an invalid certificate ([SSL: UNKNOWN_PROTOCOL] unknown protocol (_ssl.c:590))

This suggests to me that our IT doesn't have an appropriate certificate for the proxy server. My guess is that's not going to change any time soon. Am I way off in this interpretation? Any suggestions are more than welcome. I'd note that I have several other vanilla linux set ups (debian), that work fine on our network (able to pull updates without a hitch with the http_proxy set). That said, these other computers cannot find a route to smtp.gmail.com via e.g. ping (though the DNS lookup is fine), so it may be a matter of whitelisted sites for the debian update servers (To access outside sites via browsers, one must enter a password which is stored for 24h, but the proxy itself does not have a login).

Thanks in advance.
 

c32767a

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Dec 13, 2012
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The HTTP Proxy is set appropriately in the network gui (in the format: 'http://proxy.foo.bar:3128'), but this is clearly insufficient. As one might expect, I'm also unable to connect to the update server so cannot download an upgrade nor grab e.g. jail templates. I'm getting the following error attempting to access e.g. the update servers.

Host proxy.foo.bar:3128 returned an invalid certificate ([SSL: UNKNOWN_PROTOCOL] unknown protocol (_ssl.c:590))

That's an SSL error. Are you sure your proxy URL is http:// and not https:// ?
 
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