One of the things that bugged me about the countdown videos was the moment when Elisabeth visited Jim in prison and told her she was recruited for Terra Nova.
In the episode, when she told Jim she was recruited, she also said the 10th Pilgrimage would leave "next week".
In the 3th psychiatric evaluation video of Elisabeth Shannon, she said she had visited Jim. My best guess is that this video was unlocked in the Countdown app at August 22. The content of the countdown app is supposed to happen at the date it was unlocked. So, I saw a conflict.
However, I doubt that this evaluation video and the pilot episode talk about the same visit. In the pilot, the impression is given that Elisabeth bribed the guard to visit Jim. I doubt Elisabeth would tell anyone about an illegal visit. Furthermore, Jim does not respond in the pilot like he has not seen Elisabeth for a long time.
So, it could be Elisabeth visited Jim in August and visited him later in September and told him about Terra Nova and gave him the means to break out.
In the pilot, Jim first hears about Terra Nova during the illegal visit. Jim first mentions Terra Nova during his 4th psychiatric evaluation. My best guess is that this video was unlocked in the app at September 14. Not really the week before the 10th pilgrimage left, but a lot closer.
How did Jim escape?
We never see on-screen how Jim escapes from a high security prison. In Jim's final psychiatric evaluation, Jim asks if he could have "leave to go to the communications room" to make a call we know he doesn't want to make. The interviewer grants this request.
When FOX posted this video to Facebook, they added the comment: "Jim secretly lays the groundwork for his prison escape!"
I guess this means that this visit to the communications room is how Jim got out of his cell without raising suspicions. I guess that he used his laser-pen to disappear quietly from the communications room.
Thi final video was unlocked in the app at September 23. Meaning that Jim started his escape only a few days before the 10th Pilgrimage would leave. A smart move if you've got a plan.