Why does Input/Output Error Occur?

Hi folks,

Just to append to this original post.

I have tested access to this site via our no longer used, Cisco IronPort Web Security Appliances (which the Sophos UTM replaced!!) and was able to access the site fine, even with SSL Scanning enabled on the IronPorts.

Best regards,

John P

"The destination site somehow doesn't like how the UTM is intercepting the HTTPS traffic and possibly sees the resulting traffic emerging from the UTM as a Man-In-The-Middle attack?"

Yes.  If there was no such exception in the IronPort, then I would get a support case open with Sophos.

Cheers - Bob

"The destination site somehow doesn't like how the UTM is intercepting the HTTPS traffic and possibly sees the resulting traffic emerging from the UTM as a Man-In-The-Middle attack?"

Yes.  If there was no such exception in the IronPort, then I would get a support case open with Sophos.

Cheers - Bob

Hi Bob,

Thank you for your reply. It's always good to get a sanity check when these sort of things happen.

I have a couple of calls open with Sophos Support, one of which I think is quite similar to this in that their recommendation is to exempt the site from SSL Scanning as I'm getting a 'broken pipe' error message.

My main concern is the apparent lack of appetite on behalf of Sophos to resolve these problems. All that is being offered is a workaround which, let's face it, is not totally satisfactory. Having to exempt an increasing number of sites from SSL Scanning sort of defeats the purpose of scanning them in the first place.

Monday morning rant over!!

Back to work.

Thanks again,

John P

John, I ALWAYS configure to skip SSL scanning for the Finance/banking, Health and Pharmacy categories.

Did you check to confirm that you had no such exception in the IronPort?  Please do let us know Sophos' response.

Cheers - Bob

Hi Bob,

Like you I do not impose SSL scanning on sites classified as Finance/Banking. However, the site I was attempting to access on this occasion was classified (by the UTM Policy Helpdesk) as a 'Business' website with a 'Neutral' URL Reputation.

I can also confirm the the site in question (https://www.ward.ie) was not included as an exception in our old IronPort installation.

The response from Sophos, prior to closing the case, was:

"Certain servers don't like proxied traffic and in this cases the server responds in this manner. Thats the reason those URLs have to bypassed. As this is not an issue with UTM but the end server, modifying anything on UTM wont help.

If SSL scanning was bypassed for the same, the certificate TLS check is bypassed and hence proxy scanning for that website will not occur. We will definitely make note of this to our development but for now if it works, may we go ahead and close this case ?"

I'm still unconvinced that the UTM is entirely blameless in this situation as were able to access the site fine via the IronPorts. However, I'm willing to live with the minor inconvenience of creating an exception. I stated my concern to Sophos that this trend of exempting traffic from security scans did not address the underlying problem so, the ball is in their court. Hopefully it is something that will be addressed in future updates.

Best regards and thank you again for your input.

John P