I have 5 packet flip proxies I use with my browsers.

It's a paint to switch among proxies manually. Is there a program that will switch among my 5 proxies by just hitting a button?

And how do I instant message through a proxy? How do I use Outlook through a proxy?

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For outlook use the web client rather than the outlook app. For AIM use the web client at meebo.com. There's a firefox add in that lets you switch proxies easily https://addons.mozilla.org/en-US/firefox/addon/125 . Theres probably something similar for IE if you look, too, but who cares?

proxifier

Well, I have proxifier. But my HTTP proxies from packet fl1p don't work w/ OUtlook and my ftp programs.

What kind of proxy do I need? SOCKS5?

A VPN will do just fine.

For switching proxies in your browser: Foxy-Proxy, SwitchProxy, Proxy-Firewall.

HTTP proxies will not work for mail and FTP. You would need either a SOCKS proxy or look into a VPN like sdesignb has said.