Quadjumper is cloaked, Bossk has Jabba on board.

The Quadjumper rolls for end phase result for the Cloaking Device and rolled a focus.

Cloaking Device: "At the end of each round, if you are cloaked, roll 1 attack die. On a focus result, discard this card, then decloak or discard your token."

Removes 1 illicit token instead of discarding the card.

Jabba: "When you equip this card, place 1 illicit token on each Illicit Upgrade card in your squad. When you are instructed to discard an Upgrade card, you may discard 1 illicit token on that card instead."

My question:

The last part of the Cloaking Device card states that you decloak or discard the token.

When you roll a focus result and discard the illicit token because of Jabba, does the Quadjumper then have to decloak or discard the token?

I would conjecture that you do still decloak or discard because that clause is triggered by the die roll rather than the discarding of the card.

Yes you do.

The mechanics come down to rolling the focus result means you may discard your illicit token instead of the cloaking device card. Then you can either stay where you are and discard the cloak token, or preform a decloak (which also spends the cloak token).

The advantage to having Jabba in the squad being that (though when you roll the focus you are still becoming non-cloaked) you at least have the card around for at least one more shot at running cloaked.

Consider instead that BobaFett comes and removes the Cloaking Device while a ship is cloaked. Now the Cloak Token is still subject to all of its normal rules but the text from the card has been removed. Now when the CD's own effect removes it you're still doing everything even if the card is staying because you're removing the token instead.