To what extent is using the standard library considered cheating?

There was a similar discussion for grep a while back, and they eventually did add some banned packages. For your case (Python), I definitely wouldn’t be using the http.server module, but the rest is really up to you.

Update: as noted here, there is already anti-cheat, which works by checking for HTTP headers commonly set by off-the-shelf HTTP server libraries but are not expected to be set by our own custom implementations.

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