History YMMV / JailbreakRoblox

*** Speaking of which, you can only re-roll contracts if the contract hasn't been failed. If it was, then you need to wait out the timer until you can re-roll the contract, which can be bad news if you're in the middle of a firefight or a hacker spawnkilling you. Granted, the latter problem is rare, but it can be quite frustrating to wait out the timer to re-roll the contract you dislike. Also, you only get one re-roll per contract; if the re-rolled contract happens to be one you don't like, tough luck.

** The revamped Airdrop heist is a major pain to complete, in no thanks to the Bandits who can and will ignore your forcefield to riddle you with bullets. Furthermore, there is no indicator when the Bandits will spawn additional reinforcements, and compounded with the amount of time needed to open an airdrop, this means you can suddenly have Bandits dropping right into your face. And to make matters worse, while both Police and Criminals can shoot at the Bandits, in practice, the Police can use the Bandits as a distracts to sneak up on the Criminals to taze and arrest them, providing an unfair advantage to the Police unless they swarm them, which due to how airdrops don't have any robbery icons unlike the others, is not going to be noticed. And since this is the only way to obtain [[LootBoxes safes]] outside of purchasing them with in-game currency, good luck.

*** Speaking of which, you can only re-roll contracts if the contract hasn't been failed. If it was, then you need to wait out the timer until you can re-roll the contract, which can be bad news if you're in the middle of a firefight or a hacker spawnkilling you. Granted, the latter problem is rare, but it can be quite frustrating to wait out the timer to re-roll the contract you dislike.

** Casino, more specifically, the first part. You have to search around the first area to find a code to open the door to the elevator, which grants you access to the security and vault rooms. However, some of the codes can be [[GuideDangIt well-hidden without a guide to help]], making finding it much harder. To make matters worse, there's a chance for the code to ''not even spawn'', forcing players to [[LuckBasedMission brute-force the door code]]. Fortunately, once the code has been found, the rest of the heist is a breeze until the police arrive.

** Casino, more specifically, the first part. You have to search around the first area to find a code to open the door to the elevator, which grants you access to the security and vault rooms. However, some of the codes can be [[GuideDangIt well-hidden without a guide to help]], making finding it much harder. To make matters worse, there's a chance for the code not ''not even spawn'', forcing players to [[LuckBasedMission brute-force the door code]]. Fortunately, once the code has been found, the rest of the heist is a breeze until the police arrive.

* ThatOneSidequest: A few contracts have been proven to be very difficult. Most of them have been removed during Season 6, and those that did remain were simplified, for good reason:

* AuthorsSavingThrow:
** Season 6 heavily reduced and simplified all the contracts to "Rob (place) without dying!" for criminals and "Arrest X amount of people without dying!" for police while also making it that not only you automatically accept them, but you accept all of them at the same time. Granted, dying does still give you a timer before you can re-accept the contract, but since those contracts are easy to do, you pretty much can easily complete them without worrying about dying, and said contracts are auto-accepted once the cooldown time is gone. Later, when Season 7 un-simplified the contracts, they still kept the auto-accept for all contracts, allowing a player to easily complete them all in one scheduled sweep.
** The 2022 Live Event not only expanded the map, which made it easier for players to rob the Cargo Plane, but also automatically ejected them from it after a certain amount of time regardless if they have a Keycard or not, which is useful for players who have "Rob the Cargo Plane without dying!" contract since prior to that, if they didn't have it, they have to get lucky with getting the cargo that has the Keycard or risk getting killed.

** Bank Heist has become this thanks to the July 2021 update. This heist was a semi-decent way for Criminals to make money, and was one of the first heists to be released. However, that all changed when the Police HQ was added to the game. Where is that location, perhaps? Well, it's ''right near the bank''. Because of this, robbing the bank is much harder than usual given that police will spawn right near it just in time to arrest the criminals involved. The Presidential Vault bank floor deserves special mention, because [[UpToEleven even the police can have trouble entering the vault to arrest all the criminals inside the bank]], due to the moving lasers that can throw multiple players off even without lag, resulting in multiple failed attempts to enter the vault. Quite fittingly, it has one of the biggest payouts in the game at around $7,200.

* AuthorsSavingThrow: Season 6 heavily reduced and simplified all the contracts to "Rob (place) without dying!" for criminals and "Arrest X amount of people without dying!" for police while also making it that not only you automatically accept them, but you accept all of them at the same time. Granted, dying does still give you a timer before you can re-accept the contract, but since those contracts are easy to do, you pretty much can easily complete them without worrying about dying, and said contracts are auto-accepted once the cooldown time is gone. Later, when Season 7 un-simplified the contracts, they still kept the auto-accept for all contracts, allowing a player to easily complete them all in one scheduled sweep.

** "Rob the Cargo Train and Passenger Train without dying!" seems simple enough... Until you realize that due to the way how trains spawn in Jailbreak, there's a ''very'' good chance that the Passenger Train might not spawn at all, even when buying a train spawn in the Control Tower in nighttime or during a storm. What makes it worse is that if you die, you have to start over again. Season 6 later made it so you that you can rob either train once and you can complete the contract easily, and while it did made a return in Season 7 for a brief while, it was later replaced afterwards.
** "Arrest (certain amount of money) worth of criminal bounty without dying." The CrooksAreBetterArmed trope is in full force here, and unless you gang up on an unsuspecting Criminal, expect to see the "FAILED" screen a LOT.
** "Rob the Bank without dying!" and "Rob the Museum without dying!" See ThatOneLevel for more details.

** "Rob the Money Truck without dying!" Aside from the fact that you're attacking a heavily defending Bank Truck which is notoriously skewed towards police without criminals using a Blackhawk, there's also the matter of starting the heist in the first place, as seen in ScrappyMechanic. Expect to take potentially ''hours'' for the Bank Truck heist to start.