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Is the SOCKS5 proxy on the same machine, or is it a separate one?

It would also help to say WHY you want to do this. We might be able to suggest some alternatives.

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Sounds like the OP wants to be sure that all traffic is going through the proxy (much like the TOR liveCD claims to do).

It's easier to proxy specific applications. If the application supports SOCKS proxies you can configure it directly. If it does not you can use a utility like tsocks or proxychains to sort of trick it into using a SOCKS proxy (it hijacks the system-calls and redirect network traffic through the proxy.)

Doing it system-wide is a bit more complicated, and depending on the circumstances, potentially ill-advised.

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