Hi, I got frustrated searching for a solution for this problem here, I didn't see anything useful other than "why you wanna do that huh" and "I think the proxy is blocking winamp", well DUH I already knew that, so I solved it myself instead and figured I'd share the fun because I LOVE the Winamp community, it's that simple. 
Problem 1:
THE corporation, with an anal content filter on their proxy, killing both music and surf for me, the busy bee employee.
Solution:
Port forwarding via an encrypted proxy tunnel. I'm not going to write all the details for that here, since this is Winamp.com, so I'll stay on topic for the forum. I'm assuming you have an SSH server at home, and that your're using Tunnelier or Putty to "phone home". Your tunnel works already for surfing, and I assume you're using Firefox to disable DNS leakage via about:config, but you keep getting the [Error syncing to stream] in Winamp.
Problem 2:
Trying to listen to aacPlus or any shoutcast streams in general from .pls files in Winamp will render an [Error syncing to stream] in Winamp, despite you having entered the correct proxy settings, as in pointing to your Tunnelier or Putty forwarding port.
Solution:
Since the actual problem is, that Winamp is expecting a HTTP proxy, and the ones mentioned above use SOCKS, the solution is to set up another proxy on your work computer, for example the simple, brilliant and "free for up to three users" Youngzsoft CCproxy. I use one install at home and one at work now for this to work, btw.
So, with a working tunnel already in place, add CCproxy on work comp, with a cascading proxy setup, so it forwards to the SOCKS forwarding Tunnelier or Putty, via the CCproxy HTTP proxy port. Make sure to avoid port collisions, and to disable the HTTP forwarding in Tunnelier, just use the C2S port forward. Also make sure to use the built-in IP-masking in CCProxy so it only allows localhost IP.
You then tell Winamp to use the CCProxy, which forwards to Tunnelier or Putty, which forwards encrypted stuff to the corporate proxy, which forwards home, which in turn hooks me up to where the fun is at.
Yupp yupp.
Having set up the above correctly, I now have any .pls webradio anhywhere in the world available at work. I'm also smart enough to use the aacPlus ones, for like 24-36 Kbit bandwidth, so I generate low amounts of traffic to stay under the radar.
Oh, this also works for the dreaded WMP .asx ones, but that crappy program keeps opening the "Now playing" for the .asx files, so even though I get the stream playing, I also generate a "content denied" page from my corporation, which is conspicuous if it happends alot. If you solve that, please reply to this thread with the solution since WMP defaults to the IE settings for the "Now playing", and I need IE untouched for the internal corp stuff.
If this helped you, I'm glad, and the beer is on me. Cheers from Sweden.

Problem 1:
THE corporation, with an anal content filter on their proxy, killing both music and surf for me, the busy bee employee.
Solution:
Port forwarding via an encrypted proxy tunnel. I'm not going to write all the details for that here, since this is Winamp.com, so I'll stay on topic for the forum. I'm assuming you have an SSH server at home, and that your're using Tunnelier or Putty to "phone home". Your tunnel works already for surfing, and I assume you're using Firefox to disable DNS leakage via about:config, but you keep getting the [Error syncing to stream] in Winamp.
Problem 2:
Trying to listen to aacPlus or any shoutcast streams in general from .pls files in Winamp will render an [Error syncing to stream] in Winamp, despite you having entered the correct proxy settings, as in pointing to your Tunnelier or Putty forwarding port.
Solution:
Since the actual problem is, that Winamp is expecting a HTTP proxy, and the ones mentioned above use SOCKS, the solution is to set up another proxy on your work computer, for example the simple, brilliant and "free for up to three users" Youngzsoft CCproxy. I use one install at home and one at work now for this to work, btw.
So, with a working tunnel already in place, add CCproxy on work comp, with a cascading proxy setup, so it forwards to the SOCKS forwarding Tunnelier or Putty, via the CCproxy HTTP proxy port. Make sure to avoid port collisions, and to disable the HTTP forwarding in Tunnelier, just use the C2S port forward. Also make sure to use the built-in IP-masking in CCProxy so it only allows localhost IP.
You then tell Winamp to use the CCProxy, which forwards to Tunnelier or Putty, which forwards encrypted stuff to the corporate proxy, which forwards home, which in turn hooks me up to where the fun is at.

Yupp yupp.

Having set up the above correctly, I now have any .pls webradio anhywhere in the world available at work. I'm also smart enough to use the aacPlus ones, for like 24-36 Kbit bandwidth, so I generate low amounts of traffic to stay under the radar.
Oh, this also works for the dreaded WMP .asx ones, but that crappy program keeps opening the "Now playing" for the .asx files, so even though I get the stream playing, I also generate a "content denied" page from my corporation, which is conspicuous if it happends alot. If you solve that, please reply to this thread with the solution since WMP defaults to the IE settings for the "Now playing", and I need IE untouched for the internal corp stuff.
If this helped you, I'm glad, and the beer is on me. Cheers from Sweden.
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