Hmm... it depends on which priority the role have taken.

I don't mean to get into heavy theory or anything - I'd leave that to Jude or Rowen - but there's a thing called Natural Action Resolution that clarifies in what order power role actions are executed. The order becomes important when there's many night actions all activating at once!

When I was looking up grinding, I also decided to do a spot of reading to help us defeat the traitors, and came across the Natural Action Resolution. Basically, roles that have higher priority would override ones below in cases of conflict. Here's the list, and I've also provided a link here:

Commute - Commuter
Blocking - Roleblocker, Rolestopper
Jailkeep - Jailkeeper
Protection - Doctor, Bodyguard
Miscellaneous - Neighborizer, Friendly Neighbor
Kill - Mafia factional kill, SK factional kill, Strongman, Vigilante
Role Investigation - Cop, Gunsmith, Role Cop, Vanilla Cop, Neapolitan
Action Investigation - Tracker, Watcher, Voyeur, Follower, Motion Detector

So in the event that a Roleblocker and a Jailkeeper targeted each other, the Roleblocker would prevent the Jailkeeper from keeping. At least, that's if you were following the list laid out in this book I was reading. Supreme Overlord Kohaku might've followed another procedure.

It does get so confusing though. Here's an example found on the Roleblocker that makes my head hurt:

Quote Originally Posted by Of Mafia Bondage by Milla Maxwell
Suppose Roleblocker A blocks Roleblocker B, who blocks Roleblocker C, who blocks Roleblocker D, who blocks Doctor E. If Roleblocks are resolved in such a way that conflicts are minimized, A blocks B, preventing B from blocking C, thus C blocks D, preventing D from blocking the Doctor - in short, the Doctor's protection would have an effect. If all Roleblocks are simultaneous, the only player who is NOT technically Roleblocked is A; the Doctor would be blocked.

I guess ultimately it is up to Kohaku how she would resolve such confusing instances! I will say though that 'cancelling each out out' implies both abilities were allowed to fire - as in, both the Roleblocker and the Jailkeeper were allowed to activate their ability. If the Roleblocker is above the Jailkeeper in priority, then the Jailkeeper would never be allowed to activate their ability, and so I would question the use of the term 'cancellation'.

This is all assuming the Jailkeeper and Roleblocker are the two roles in question here. It's hard to speculate at this moment because we don't know if they're in the game, or if they targeted each other.

But hopefully I've put forward a possible suggestion as to how night actions might be resolved? What Raven says can't be proven, but it can't be denied also.