I think removing a Thief from Gaol automatically makes them “Free”, so the second sentence is redundant.

Also, because a Thief in Gaol cannot take dynastic actions, even “lose a Lockpick” can’t be done, because it’s a dynastic action.

If you want to allow this, you’ll have to change that wording in the rule. Something like this:

A Thief who is in Gaol may not take dynastic actions, except for the following specific actions:
* If a Thief in Gaol has a Lockpick in their inventory, they may remove it from their inventory and then remove themselves from Gaol

We can then add to list any other dynastic actions that Thieves in Gaol should be able to take.

If you do make that change, be sure to preserve the latter part of that rule:

is always considered to have a Plan of “Rest” and an Attitude of “One of Us”.

It’s probably best just to add “A Thief who is in Gaol” to the beginning of that second statement as a separate paragraph.

I thought Prioritisation might work there, but it does look like it doesn’t clear the bar of “the part with more limited scope applies” and so falls at “the negative rule applies”.

Updated.

I may need this someday <.< >.>