There's no personal risk to writing regime circumvention tools. Iran isn't going to have you assassinated for your work on Tor.
There is serious risk to using Tor in Iran. Death squads and disappearances aren't a conspiracy theory in Iran; they are the regime's well-understood M.O. When circumvention tools like Tor work, they hide your traffic from the regime. When they stop working, or are turned, they do exactly the opposite: they attach a statistical marker to your traffic that says "whether or not you can read these packets, the person sending them is interesting".
The people working on circumvention tools are mostly well-intentioned (many of them are friends of mine), but they are delusional about the SWOT analysis at play here. None of them have any unique skills that aren't available to an organization willing to shell out 6-7 figures to a team in a month. Money buys competence. A lot of money buys a lot of competence. Iran has a lot of money. Circumvention projects do not.
Kickstarter hasn't seen the amount of money that a world government could spend without director-level approval on a project to turn a circumvention tool against its users.
And that's before you get to the fact that many, if not most, of the computers in authoritarian regimes are probably already rootkitted.
While I agree with most of your post, I do have to take issue with this statement:
"There is serious risk to using Tor in Iran."
While there certainly is a chance of getting in trouble for using Tor, I wouldn't classify it as "serious risk." The government in Iran faces a situation w.r.t. filter circumvention similar to what the US faces when cracking down on illegal file-sharers. From my (admittedly limited) experience in Tehran last year, anyone with even a little computer know-how will have either some proxy service or Tor installed on their computers. The more knowledgeable ones have their own VPNs. Most use it to get through to Facebook and chat with their friends. It would be impossible to persecute everyone who's used circumvention tools without emptying half of Tehran.
The government certainly doesn't shy away from the measures you mentioned, but they generally go after for more grievous "offenses" than browsing the internet through Tor. Being gay, for example.
All the competence in the world won't let you break basic crypto algorithms without at least breaking a sweat.
The playing field between Alice and Bob on the one hand and Eve on the other hand is inherently asymmetrical. Given equal competence and time to work on it, Alice and Bob are going to come up with an encryption scheme that Eve won't be able to break. You seem to be convinced that given almost unlimited resources, Eve can break any scheme Alice and Bob can come up with. I'm not sure I see any evidence for that.
In some cases, Eve is willing to arrest/maim/kill anyone caught using Bob's encryption scheme. Eve has the ability to control at least some of the intermediary systems. Eve doesn't need to specifically break the scheme, just be able to figure out who's using it so she can go apply some lead pipe cryptanalysis [0].
I don't think he's saying that at all. I interpreted it as, given unlimited resources, Eve can determine that Alice and Bob are communicating over encrypted channels which, for Alice and Bob, is almost as bad as having their encryption broken.
I took that to be a specific example -- Tor may be detected using traffic analysis -- of a more general principle -- circumvention tools can not hope to withstand nearly unlimited resources. I thought tptacek was pretty explicit in making this more general statement.
One thing that a lot of circumvention tool promoters get wrong is the threat model. The threat model isn't "attacker can read your traffic" --- although some of the best known circumvention tools have made cryptographic mistakes that did allow that. The threat model is "tractable attacks that isolate traffic using your tool from bulk Internet traffic".
A torture cell will do just peachy at decrypting the actual packets.
There's no personal risk to writing regime circumvention tools. Iran isn't going to have you assassinated for your work on Tor.
There is serious risk to using Tor in Iran. Death squads and disappearances aren't a conspiracy theory in Iran; they are the regime's well-understood M.O. When circumvention tools like Tor work, they hide your traffic from the regime. When they stop working, or are turned, they do exactly the opposite: they attach a statistical marker to your traffic that says "whether or not you can read these packets, the person sending them is interesting".
The people working on circumvention tools are mostly well-intentioned (many of them are friends of mine), but they are delusional about the SWOT analysis at play here. None of them have any unique skills that aren't available to an organization willing to shell out 6-7 figures to a team in a month. Money buys competence. A lot of money buys a lot of competence. Iran has a lot of money. Circumvention projects do not.
Kickstarter hasn't seen the amount of money that a world government could spend without director-level approval on a project to turn a circumvention tool against its users.
And that's before you get to the fact that many, if not most, of the computers in authoritarian regimes are probably already rootkitted.