Can you break through the level cap by going to jail? [duplicate]

Solution 1:

No you can't. In Skyrim you only lose progress towards one or more skill advancements, not already increased skills.

Source: UESP and ingame loading screens.

Solution 2:

No, going to jail will not lower your skills nor raise your level cap.

On PC, you can use Uncapper along with SKSE in order to raise the level caps. You can modify the script to be virtually unlimited, but the level cap is raised to 300 using Uncapper mod. Uncapper is a "plugin" for SKSE so you must have SKSE installed to use Uncapper.Without Uncapper I would no longer have any interest continuing playing Skyrim after I'm maxed out.

Here's the link to the Uncapper mod: http://skyrim.nexusmods.com/mods/1175/
and here's the link to SKSE: http://skse.silverlock.org/