This AP story describing the backstory of USAID contractor Alan Gross’s imprisonment in Cuba is interesting in its own right. Past reporting had made it clear that Cuba had declared Gross a spy because he was setting up secure communications technology for Cuba’s Jewish community.

Gross’ company, JBDC Inc., which specializes in setting up Internet access in remote locations like Iraq and Afghanistan, had been hired by Development Associates International Inc. of Bethesda, Maryland, which had a multimillion-dollar contract with USAID to break Cuba’s information blockade by “technological outreach through phone banks, satellite Internet and cell phones.”

The AP story describes the vast array of telecom equipment Gross and some Jewish humanitarian groups he partnered with smuggled into Cuba, where some of it is explicitly prohibited:

12 iPods, 11 BlackBerry Curve smartphones, three MacBooks, six 500-gigabyte external drives, three Internet satellite phones known as BGANs, three routers, three controllers, 18 wireless access points, 13 memory sticks, three phones to make calls over the Internet, and networking switches.

And it explains what it was that finally got Gross arrested: his importation of a “discreet” SIM card that would make it impossible to track satellite phone transmissions.

On his final trip, he brought in a “discreet” SIM card — or subscriber identity module card — intended to keep satellite phone transmissions from being pinpointed within 250 miles (400 kilometers), if they were detected at all.

The type of SIM card used by Gross is not available on the open market and is distributed only to governments, according to an official at a satellite telephone company familiar with the technology and a former U.S. intelligence official who has used such a chip. The officials, who spoke on condition of anonymity because of the sensitivity of the technology, said the chips are provided most frequently to the Defense Department and the CIA, but also can be obtained by the State Department, which oversees USAID.

So Gross was arrested for trying to make sure a subset of Cuba’s population could access the Internet in privacy.

Back when Alan Gross was “convicted,” the White House officially condemned the decision, as they’ve condemned his treatment repeatedly since.

Alan Gross has been unjustly detained and deprived of his liberty and freedom for the last 14 months. Instead of releasing Mr. Gross so he can come home to his wife and family, today’s decision by Cuban authorities compounds the injustice suffered by a man helping to increase the free flow of information, to, from, and among the Cuban people.

We remain deeply concerned for Mr. Gross’ well being and that of his family and reiterate our call for his immediate release.

Gross’ case would make you think the government inherently valued secure Internet communication.

But compare their treatment of Gross with the treatment they’ve given Jacob Appelbaum, the Tor researcher who they’ve treated like a suspected terrorist.

Tor, like the communications equipment Gross was installing, makes it easier for dissidents and other members of civil society to communicate freely.

Tor is a network of virtual tunnels that allows people and groups to improve their privacy and security on the Internet. It also enables software developers to create new communication tools with built-in privacy features. Tor provides the foundation for a range of applications that allow organizations and individuals to share information over public networks without compromising their privacy.

Individuals use Tor to keep websites from tracking them and their family members, or to connect to news sites, instant messaging services, or the like when these are blocked by their local Internet providers. Tor’s hidden services let users publish web sites and other services without needing to reveal the location of the site. Individuals also use Tor for socially sensitive communication: chat rooms and web forums for rape and abuse survivors, or people with illnesses.

Journalists use Tor to communicate more safely with whistleblowers and dissidents. Non-governmental organizations (NGOs) use Tor to allow their workers to connect to their home website while they’re in a foreign country, without notifying everybody nearby that they’re working with that organization.

And like Gross, Appelbaum has traveled internationally to help foster such private communications. If you follow him on Twitter, you can even see him tracking and responding to attacks on secure networks in the Middle East.

So if Administration expressions of concern about the free flow of information were sincere, you’d think they’d be celebrating Appelbaum’s efforts.

Instead, partly because of his ties to WikiLeaks, they routinely harass him. Not only have they subpoenaed his Twitter IP information and a slew of other data as part of their WikiLeaks investigation, but every time he returns to the country, they temporarily detain him. Whereas with Gross in Cuba, authorities were looking for equipment that was actually illegal under its laws, our border guards are trying to get to Appelbaum’s First Amendment protected data (which, on a recent occasion of such harassment quite literally consisted of the First Amendment).

• The CPB specifically wanted laptops and cell phones and were visibly unhappy when they discovered nothing of the sort.

• I did however have a few USB thumb drives with a copy of the Bill of Rights encoded into the block device. They were unable to copy it.

• The forensic specialist (who was friendly) explained that EnCase and FTK, with a write-blocker inline were unable to see the Bill of Rights.

[snip]

• All in all, the detainment was around thirty minutes long. They all seemed quite distressed that I had no computer and no phone.

• They were quite surprised to learn that Iceland had computers and that I didn’t have to bring my own.

• There were of course the same lies and threats that I received last time. They even complemented me on work done regarding China and Iran.

• I think there’s a major disconnect required to do that job and to also complement me on what they consider to be work against police states.

[snip]

The CBP agent asked me for data – was I bringing data into the country? Where was all my data from the trip? Names, numbers, receipts, etc.

Our government, from the White House on down, has decried the treatment of a man trying to ensure the free flow of information. And yet, it similarly–though not (thus far) as severely–criminalizing efforts to ensure the free flow of information.