itch.io

I wouldn't know how to help you without more information. Please go to the help channel in the disord.

You can also just switch the game to easy mode and it will guide you through the punishments automatically.

Just switch to easy mode under preferences and restart the punishment. You'll have the option to be guided through automatically.

FYI - The public release is being delayed while I work on some extra content for version 0.17. I've posted about it publicly on my Patreon page. 

I can't post the link though. It seems that Itch doesn't allow developers to post links to their own Patreon, even though I have to delete several fake links from scammers every day.

Just switch to easy mode under preferences then restart the punishment for guided mode.

A new version is out for patrons. I'll release it here for free soon enough.

Usually people get stuck here because they didn't spy on Cassandra after spanking her after school.

The latest version is out for patrons on the $10 and above tiers. It will be released to $5 and above tiers next Friday and it will be here for free January 16th.

I will be releasing it to Patrons on December 12th. It will be here for free on January 16th.

There might be another quest-line conflicting with Cassandra's. Trying checking the shower room. If you can't figure out what to do just carry on with different quests and come back to it later

It only works on Monday afternoons.

From our FAQ: To find Sally's keys:

You need to complete the first main quest 'order to the chaos' and have stolen the big towel. Only then will Jimmy give you the keys.

(You need to open the lake during the Friday meetings to be able to talk to Jimmy during the weekday about it.)

to complete 'order to the chaos', the following needs to be done: (the night after completion, a cut scene plays)

1)Get Discipline to 20.

2)Complete the first scene that Miss Potts cosplays as a student.

3)Hire a Lab Assistant for Miss Chang, and tell her you have done so.

4)Give Priti's password to Wilson.

5)Pass any rule

To steal the towel, visit the men's showers twice on a Monday afternoon, stealing the towels on the second visit, and then talk to sally right after

With easy mode it is literally automatic. You don't need to do anything.

I promise you it does work. Either you haven't met all the prerequisites, or you aren't using the right actions. At the start of the punishment it will tell you if the girl is ready to level up. If she is, switch to easy mode under preferences and the game will walk you through the right steps. If she isn't ready to level then see what the hint says to do next, or check the quest log.

Just switch to easy mode under preferences and it will guide you through the steps.

You can switch to easy mode under preferences and you will have the option to be led through the punishment automatically.

The changes from 16.4.3 to 16.4.4 were pretty tiny, and I know it works for most people. We did switch to the latest version of Renpy, so maybe that's the issue. Without seeing the log file, I can''t really give you much advice. I would suggest going onto out Discord help channel and posting the log file there. 

There are a few basic troubleshooting issues that you can try as well.

1. Delete the persistent file:  A corrupted save or persistent file is a common cause for a game not launching. 
   • Navigate to %appdata% on Windows. 
   • Find the Renpy folder and then locate the specific game's folder. 
   • Delete the persistent file to clear corrupted save data. 

2. Update graphics drivers.

I've also seen people say fixing issues with Renpy games not starting is as simple as renaming the folder it's in. I'm afraid I can't verify or test any of these this as the game runs fine on my computer.

At the weekly board meeting. Under other rules.

To play with Joiplay you need to download the windows version.

The itch app is the best way to download the game on Windows or Mac

The last three updates had about ~180,000 words of dialogue in them (all together) several thousand renders and hundreds of videos. Either you are an insanely fast reader or you have missed/ignored/skipped the vast majority of the content. I would advise you to check the event log (top right button in the main map). Also, content decisions are based on Patreon polls. I’m afraid the science teacher has never been highly requested.

It could be that you need to punish Cassandra, even it it says "not ready to level up". Then spy on her room.

Updated walkthrough link, couple of very minor bugs fixes.

No date set, but I am aiming for a mid-late October release for patrons.

I mean... Maybe you have your answer then.

Probably because some other event is blocking it. Work on the other quests and come back to it.

I post detailed monthly progress reports on Patreon and SubscribeStar.

There is a lengthy walk through. You can find a link to it in the cheat menu (press the big red button 3 times). Alternatively there are hints to all the horniness points in the quest log. 

The full version is available here completely for free. The game is not available on Steam.

It's like holding back the tide, my friend. I just have to keep deleting these stupid links.

The version on Itch is the latest version, just download the game again. saves will transfer automatically.. No patches are required. 

If you head over to our Discord someone will be able to help you. https://discord.gg/Btnw9z7tan

Yeah, pretty sure I'll be fine. Stuff like this happens every so often and usually blows over. I've always been careful to stick to Patreon's terms and conditions (also dictated by payment processors), so I should be good.

I'm still working on it. Next update is likely to be in the fall.

Ruth's exam will mark the end of Chapter 2, but that won't be in the next update (which will have the punishment system for Faye and the Twins). The end of Chapter 2 will likely come in version 0.18 next year sometime. Games like this are extremely time consuming to make unfortunately. 

The next version will be 17.0 coming later this year. October would be my best guess at the moment.

From our Discord:

Known Good Versions - April 2025

JoiPlay 1.20.590 https://joiplay.net/repo/joiplay/1.20.590.apk Ren'Py 8.2.3 Plugin 1.00.70 https://joiplay.net/repo/renpy8.2.3/1.00.70.apk You CANNOT use the Ren'Py 8.3.7 plugin to play v0.16 of The Headmaster, it will crash the game on launch. You can install both plugins on your device and Joiplay will pick the right one, but if you only have the 8.3 plugin, it will fail.

There was a bug like that in an older version. Make sure you're playing the most up to date version from this site.

Probably sometime in October on Patron and it'll be here for free around November.

Why not just use easy mode then? The puzzles are entirely optional.

It's a windows app. I've got it on my PC.