[Pecos_Bill (OP)]

I take note of reports that Syrian government IT is being used to hit opposition computers with malware and to ID opposition members.

In the science fiction book "Little Brother" VPN and "Onion Router" technology are used to protect people opposed to an evil version of homeland security.

Are these effective in the current milieu?

[Mazurka]

As I understand, connecting to onion routers (such as TOR) via VPN will make determining a server's location more or less impossible.  Due to the way that each layer of the "onion" encrypts and decrypts it is not possible to meaningfully intercept data, except where it leaves the system
 
However, it is still (theoretically) possible using a combination of surveilance techniques to identify/ monitor users by looking at the systems that they log into that are outside the TOR network...

Encyption using Pretty Good Privacy (PGP) provides (what is thought/ assumed) to be an unbreakable way to transfer data (files, emails etc) assuming that it is used properly.  The weakness in this system sits facing the monitor.

[FunkyWorm]

The best explanation of how TOR works can be found on Steve Gibson's "Security Now" podcast; http://twit.tv/sn70 [nofollow]. As I understand it you can even have compromised machines along the route but so long as there are at least three "free" machines in the onion then your traffic is entirely anonymous (but slow!).
There is one problem that if you monitor the inlet and outlet nodes it might be possible to match incoming IPs with outgoing packets just by observing their timing, but TOR2 apparently gets around this by inserting random timing fluctuations into the packet stream.

[RD]

If you use Tor but don't encrypt the message, the exit node in the Tor network can read the message ...

By necessity, however, the last node through which traffic passes has to decrypt the communication before delivering it to its final destination. Someone operating that exit node can therefore read the traffic passing through this server.

http://www.wired.com/threatlevel/2010/06/wikileaks-documents/

Anyone can volunteer to be part of the Tor network , so if you don't use "end to end encryption" [ like PGP as suggested by Mazurka above] you should assume anyone can read what you are sending via Tor, [ the sender may be identifiable by the contents of the message ].

[evan_au]

When using the internet in China, I was not particularly surprised to find some websites blocked - I had previously heard of the "Great Firewall of China".

Governments can block websites they don't like, including onion routers (if they can recognise them fast enough). Alternatively, they could choose to block particular protocols or encrypted streams.

Worst of all, generating encrypted streams may draw attention to the very people who want to avoid attention!

It may be better to use steganography to hide messages where people don't expect to see them. Of course security organisations will be on the lookout for this too...

[yor_on]

Or we can pass international laws restricting governments and business interests tampering with our Internet. That way, if a country/government spy on you, you at least can take it to a international court, not domestic nota bene It all depends on how much we value personal integrity, and what 'trust' we are prepared to give our national institutions. In the end it's not what we have that should decide that though, but what we might get.

[Schema]

I am not sure I entirely understand your question. As stated a few times, end point isn't encrypted. But depending on what your agenda is, TOR may or may not suit your needs. If you are worried about someone tracing your logs back to you, that is impossible. It would take years to trace logs, even for a  government. Eventually, your logs will be traced back to a hop in a country that has no discourse treaty. Tor equals anonymity. You can also point your applications to tor to hide various things like port scanners and the like.

If you are worried about the encryption of your information, I would suggest renting a VPN and using a version of linux so you can freely change your mac addy.

I will mention that it has been rumored that the United States Government own/control some of the hops you hit along the way. Of course it is just rumor fueled by NSA conspiracy. There is no real way to verify that.

[evan_au]

A recent podcast on different ways to secure your digital life (21 minutes):
http://www.sciencefriday.com/segment/07/12/2013/protecting-your-online-privacy.html

[Szostak]

In the case of FBI to arrest that guy on UK ( i believe) they used some javascript to inject some malware code into the readers, and revealing their MAC adress, then using geolocalization on them. My solution would be using a virtual machine, spoofing the mac adress, using a VPN, paid one, as those free are most likely not to fight for your privacy in court, and also using a good firewall (it'd be good if we could resolve IPs right on the firewall, to see if they come from the site we're visiting).

At least i hope i'm half right D: .