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Well, while it may be easy to DF a shortwave signal if you have
adequate resources (like the government's), it's nearly impossible to
tell who is receiving that transmission.

Point taken, but DFing a signal doesn't require government-level
resources.  I've participated in a few DF events before, none of them
using anything much more complex than a directional antenna for the
band we're working and the signal meter built in to the radio.
Granted, there's much better hardware out there to do it with - but
remember that it was a couple of hams who found Yosemite Sam, not the
FCC (although that's likely another story in and of itself).

In the web world- however, there's a log for everything.

Yes and no.  Things get logged, assuming that:

a) Logging is enabled.
b) There's space to store the logs.
c) The logs aren't rotated and written over.

Every person
who visited that Craigslist link is logged.

We can't say that for certain because we don't know Craigslist's
logging policies.  More:

The poster himself was
logged.

While this is likely the case, again, we don't know their policies on
logging.  And, of course, that doesn't cover the logs the VoIP
providers have, or any of the other websites that were following the
experiment.  Further, just because logs exist doesn't mean that access
to them by third parties (such as law enforcement, or the intelligence
community) is automatic.

Following on from that, though, we can probably *assume* (note the
emphasis) that people from the original poster on down were logged.
However, it's important to remember that there are any number of ways
to obfuscate an IP address: use a public access terminal such as in an
Internet cafe or library; use a proxy or similar anonymizing service;
route your traffic through compromised machines.  There are others,
but that should serve to demonstrate the less-than-useful nature of
relying on an IP address when attempting to physically locate someone.

Also, there's one other thing that's probably worth pointing out: in a
real-world scenario, this likely would've been an overly-complex way
of communicating with an agent.  There are two sides to the
communication - one on Craigslist telling the agent to call a
particular number, then the actual communication to the agent recorded
on the VoIP station.  Using Craigslist alone probably would've
sufficed; the messages could've been encrypted steganographically
within posts to, say, the rants & raves section.  I'm specifically
picking rants & raves here because it's a) not uncommon to see long
messages posted there, allowing for a longer encrypted message to be
hidden, and b) there are literally hundreds of posts there on any
given day for any given city, which would again have made finding the
intended recipient extremely difficult.

With respect to the VoIP station, it worked fine as a transmission
medium both from the standpoints of availability and obfuscation:
people recorded it and made it available in many formats from MP3 to
text to radio broadcasts, so knowing the intended recipient .
However, the downfall is that it provides a second level of logging
and if you're trying to avoid leaving an audit trail, multiple levels
of logging can either work in your favour or against you - they can
either serve to baffle an investigator by overwhelming them with data,
or enable correlation of events allowing a list of suspects to be
drawn up and chased down.

And thanks to a powerful search engine like Google, one could
search a large chunk of the internet for places where "MEIN FREULEIN"
exists.

Sure.  But remember that we were never intending from the get-go for
this to be clandestine; the idea was to put a high level of
signal-to-noise around the stations by having their content spread for
us by unwitting third parties.  In a sense, this is some of the best
obfuscation you could hope for.  People already listen to shortwave
transmissions and discuss them openly; that doesn't necessarily mean
that their intended recipients are any more or less secure in their
comings and goings than if nobody had heard them in the first place.
As long as the message itself remains uncrackable and can't be tied to
a particular individual, then all it is is a bit of spurious - but
nonetheless interesting - data.

From there, it's just a matter of filtering the data, then a
quick subpeona of the telco's records for users from a certain area.

Believe me, this is nowhere near as easy as it sounds.

Posting at an internet cafe with an anonymous account isn't safe
either, due to the prevalence of cameras in such places.

Sure.  But, as mentioned earlier, that's not the only option.  And
even if one were posting from a location such as an Internet cafe,
there are steps that can be taken to very effectively make it appear
as though this is not the case.

No the best way to covertly communicate online is to open an anonymous
email account with Gmail or hotmail or something...then share the
login/password with the person you intend to communicate with.

No.  Absolutely not.  This would be about the *worst* way you could do
it.  Gmail archives *everything* and is highly-searchable; ditto
Hotmail.  Even if you're emailing encrypted content between two
parties, you've still got an established link between them, and the
email itself is in plaintext - so it's trivial to look at a message,
say, 'yup, that's encrypted traffic', and then start watching for
communication between the sender and recipient.  Decrypting the
transmitted content would be an entirely more complex matter, but at
least it'd be possible to infer that a channel of communication exists
between the two parties.  Further, working in the shared-login
scenario that you suggest, that effectively compromises the login and
exponentially widens the chances of it falling into the wrong hands.

Simply
leave messages for each other from within the same account; voila, you
avoid a lot of the risk online. You could even rot13 your one time
number pad :)

I just want to know why nobody's done rot26 yet - I mean, it should be
twice as secure, right? ;)

- skroo.
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