How safe is it to transfer sensitive information over Tor Browser Bundle on a restricted network?

I am using the Tor Browser Bundle in Ubuntu from a client machine on a restricted network. In part, I do this because it appears that TBB's native encryption allows me to bypass certain network filters which cannot inspect my data packets.

However, how safe is it to transfer sensitive information (data that I publish, sites I visit, pages I read, etc.) from within a restricted network over the Tor Browser Bundle?

Tor should protect you from your local network, if that's what you're worried about.

The problem with Tor is the exit node (whose traffic could be sniffed) but that's hard to predict or manipulate (unless you're the NSA). If you're using SSL over Tor, that's even better.

Personally, I'd opt to just SSH to a server of mine and use its OpenSSH's built in SOCKS proxy.

ssh -D 9090 user@server

Then you can set your browser's proxy (remember it has to be a SOCKS proxy, not HTTP - that won't work) to localhost:9090 and boom, your traffic is fully encrypted all the way out to the server.

• Pro: To your local network it'll also look like standard encrypted SSH traffic. Much less suspicious than Tor traffic.
• Pro: It should be faster. There's less of the deliberate snaking that Tor encourages and server bandwidth is usually pretty great. This should keep things buzzing along.
• Meh: The endpoint (where you server sits) is still vulnerable but if it's yours, you should know the network more than you'll know the network of a Tor node.
• Con: It's not anonymous. Your server? Your IP. Not yours? Keeps a log of you connecting.

I will say that Tor is not as safe as you may think. And I argue this statement with the following quote from this article: Is Tor's Anonymous Internet Still Secure?

Browsing the Web with The Onion Router, or Tor, is supposed to make you anonymous. Many of the encryption algorithms used by this popular Internet anonymizing protocol have likely been cracked by the NSA, says one security expert – and upgrading to the newest versions of Tor software won’t be enough to protect your privacy.

There's still much we don't know about the NSA's reported ability to circumvent online encryption. The Sept. 5 articles by The New York Times and The Guardian are light on details, but they suggest that the NSA has cracked a significant portion of the Secure Sockets Layer (SSL), the encrypted protocol that oversees the connection between your browser and the websites it displays.

That means 76 percent of Tor's supposedly anonymous network traffic might be crackable by the NSA, according to the findings of security expert Robert Graham, the CEO of Errata Security.

MORE: 13 Security and Privacy Tips for the Truly Paranoid

See also: Tor is Not as Safe as You May Think.