I find the point of being a good warden is not to have complete control of the Reds or even to successfully complete every round. (Of course this is a sub-objective of the grand picture and quite high up the priorities list.)
Number 1 Priority - The point of the warden is to make sure people are having fun.
-Sub Priority 1.1 - The warden is there to facilitate the playing of (Fun) games for the reds to compete in using differing cruxes such as skill in the game or general knowledge or other talents etc.
-Sub Priority 1.2 - The warden is there to provide a (Moderately) oppressive force that the Reds can scheme to overcome either on their own or as a group.
Number 2 Priority - The point of the warden is to keep order in the prison.
-Sub Priority 2.1 - The warden must keep Reds in check and under (fair) control, ushering them from game to game and stopping reds from running a muck.
-Sub Priority 2.2 - The warden must keep Blues in check and under (total) control, making sure they aren't baiting, killing without just reason. Making sure they stand in the correct places in order to effectively manage reds without succumbing themselves.
-Sub Priority 1.1 (Expanded) - If we explore a wardens ability to get Reds to do games there appears to be a high number of Red players who are in favour of playing games, winning and losing them on their own terms, whether they had the skill level high enough to compete or not. Playing games seems to be much more enjoyable (Hence directly attributing to a wardens Number 1 Priority) than deaths that incur from observational mishaps or confusion. (ie Tricky orders, Miscellaneous cell days etc.)
Even greater than that, a large proportion of highly active reds (Mics in use, conscious and aware of their actions and reactions from guards and fellow reds.) will likely get bored with regular games that appear on the maps like Climb, Obby, Deathrun, etc and will engage and have more fun (Hence directly attributing to a wardens Number 1 Priority) if they get to play or compete in original games or games that involve active creative effort from the reds themselves then the highly active reds will really enjoy themselves.
Here's a list of fun games that I've found people to really enjoy.
-Dive competitions in Pool.
-Improvised acting scenes in groups.
-Couples Prom night.
-IED teams.
-Scenes from a hat
-Ingredient restricted diner
-Catwalk of Death
-Sub Priority 2.1 (Expanded) - If we look into the biggest cause of mad and people disconnecting on the server it's quite easy to spot a couple glaring problems. As mentioned before, "Playing games seems to be much more enjoyable...than deaths that incur from observational mishaps or confusion.". A warden who implements ludicrously strict AFK AFM rules is a warden who gets bored, frustrated, and restless Reds unless he/she keeps them constantly preoccupied with games or movement. A new Red will also be quickly turned off from the server if he/she just joins and is immediately killed for a reason that they don't fully understand, and now they have to sit there for 9 minutes watching other people enjoy themselves. Not exactly congruent to a fun time right? When I use the qualifier (fair) as a additive on control I mean this from the perspective of the Red. Often times if they are attempting to follow a wardens commands and are killed without warning that what they are doing is incorrect then they will feel as if it was unjust as if they had just been informed of their mistake then they would have corrected because they want to play games. So we arrive at a possible dirty word of "Warning shots". I find warning shots can be a natural solution to this but if the warden has blues in the right places then a slight mis-movement of a Red should not warrant death as they wouldn't pose a threat to a blue.
If people aren't having fun on your jailbreak server they won't come back, we're already a niche service provider. If we alienate folk by being super strict or killing them for impossibly small details they won't have fun.
Hope this helps.