Just my $3.50, indexed for inflation:
Any questions explicitly or implicitly asking about circumventing/violating an institutional or government policy are off topic for Server Fault. Period. Do not pass Go. Do not collect unemployment when fired for cause.
I don't think we need to adjust the FAQ to clarify this -- It is implied in the first line:
Server Fault is for system administrators and desktop support professionals, people who manage or maintain computers in a professional capacity…
As a community for PROFESSIONAL system administrators is is not our place to help others break local policy. We may think the policy is stupid. We may suggest that people work with their institution/government/whatever to change the policy, and we may even discuss circumvention techniques in chat/on twitter/on our own blogs, but as professionals addressing other professionals on the main site it is not appropriate for us to advise breaking local policy at someone else's organization, or to assist people asking questions in such activities.
When questions are in a gray area we often ask for clarification in comments. If clarification isn't forthcoming within a few hours (or it becomes obvious the question is about circumvention with no legitimate technical/SA goals) the question gets zotted.
What kind of "policy circumvention" questions might be allowed? I like Shane's example:
"My firewall blocks all outbound HTTP requests due to a policy requirement; how do I get WSUS/package manager to work?"
This question is not "how do I break my company's policy", it is "We have this policy (no HTTP outbound). We also have a business need for this piece of software (WSUS). Can I make WSUS work in the context of this policy, or do we need to craft exceptions?"
What kind of "policy circumvention" questions should not be allowed?
My employer only allows outbound SSH to corporate-controlled sites - What techniques can I use to bypass this block and SSH into my remote machines?
No -- the policy says "No SSH", and you're asking us how to do something your employer forbids. Quite probably for good (legal) reasons.
My employer blocks Facebook. How can I get on Facebook?
No -- C'mon, be serious. What's the business case for Facebook? MAYBE for the marketing department, in which case they can have IT craft a firewall/proxy/blacklist exception for the people who need it.