SSL Traffic Inspection - Wrong certificates returned

gshergill

Hi,

Sorry if this is the wrong category, wasn't sure which this would fall under.

Essentially the situation is this - We have two externally facing services, for which we have COMODO certificates. When you perform an openssl command (openssl s_client -showcerts -connect wiki.domain.com:443) externally from the firewall'd network we see the COMODO certificates. However, in the network (e.g. from the box running the services) we don't see the COMODO certificates, we see self-signed certificates.

As a result, a feature on the services doesn't work, as it tries to verify the validity of the other, and self-signed certificates are not accepted.

I posted on stackexchange and someone suggested the following:
"Most likely you have a proxy that uses a self signed certificate in order to inspect SSL traffic, some Secure Web Gateway solutions such as McAfee, Cisco, or Websense use a self signed certificate that users install in their computers in order to inspect encrypted traffic for malware prevention, so what you are seeing is the self signed certificate used for the proxy, you should contact the network engineers in your company in order to be sure."

We don't have SQUID configured (as far as I can tell) so I don't think this is the problem, but I'm not sure if there is anything else on pfSense which could be causing this.

Thank you.

Kind Regards,

Gary

johnpoz

here is the thing you say from inside? Your still going to the public IP? This is not going to be a good setup.

Setup how overrides in your network so when you try and go to www.somedomain.tld ie your public fqdn tha on the internet resolves to your public IP.. Internally it will resolve to the private IP address of the box running your ssl services.

gshergill

Hi,

I'm not entirely clear on what you mean, sorry.

So we have a server, orion, running both of these services. If I ping one of these services via their public fqdn, say wiki.domain.com, I see it's public ip address (same with the other service too).

Is this not the setup you are suggesting?

Thank you.

johnpoz

U the want to get back the private ip when your private your on the machine or on the same local network so why should u go to public ip which ia on your router to be reflected back in when your on the same network

gshergill

Hi,

Thanks, I changed the hosts files to point locally to our proxy server (e.g. wiki.domain.com points to the local ip of the proxy) and this is working great now, the COMODO certificates are returned and the application works.

Thanks for the help.

Kind Regards,

Gary