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Message: [QUOTE="Matt T., post: 4503456"] Fixed! I just wanted to get this into the archives, in case anybody else has this same problem later. It turns out that PGP Desktop 9, of all things, was causing problems. PGP Desktop 9 installs a Winsock 2 service to allow it to do on-the-fly IM and e-mail encryption without interacting with IM and e-mail applications. Even though I had the option to do this encryption turned off, it was still interfering with Ruby. The fix is to use LSP-Fix (available from [URL]http://www.cexx.org/lspfix.htm[/URL] ) to get rid of the PGPISP.dll (I believe that's the exact name -- the DLL doesn't show up once removed) service from your Winsock stack. Click on the "I know what I'm doing" check-box, move said DLL to the right hand column and then click "Finish". Ruby should start working from then on. I'm still doing research to make sure everything came out OK. I'll update this thread if I more information comes to light. -Matt [/QUOTE]