I'm not going to sugarcoat it. I want to install a game to my thumb drive so I can play at home, but then pick up where I left off on my work computer. I also don't want the game to leave any traces behind. I know different games have varying requirements on where files go and I'm namely talking about the OLD games in DOSBox wrappers like Zork and Planetfall.

Would this be at all possible?

According to This Thread, it should be possible.

How "portable" a game is depends on the game. Some will write entirely to their own game folder (eg, store settings in a local .ini and save game saves in a local \save subfolder). Others may well write a registry entry. It's hard to tell which is which as it varies so much per game. What you could do is search PCGamingWiki for each game, and scroll down to the "Game Data" section. If both config files & save game are something like path-to-game\ then they stand a good chance of being "portable".

For old DOS Games, it may be unlikely GOG installers "out of the box" will set it up like that, but you should be able to download the normal version of DOSBox or ScummVM and set them up via your own dosbox.conf file to run off a USB drive and point towards data files on save drive. Other source ports, eg, GZDoom are 100% portable. Obviously it's advisable to try and make sure the USB drive has the same drive letter on both PC's (something you can change in Computer Management -> Disk Management -> Right-click -> Change drive letter).

All Unity games store a bunch of settings in the registry. But you can delete them every time using the command line or a .reg file.

No personal games on company hours! :p

You can stick a whole operating system along with the game on the thumb drive. This way it won't mess with what's installed on the computer.

That's the best way. Boot into Linux and keep dosbox on the live USB.

Not sure where you work but you may be making a lot of assumptions about network security where you work. This would not be possible on the network I administer due to group policies, but I've managed many networks that run screen recording software on all the employee devices.

How does the screen recorder work if I boot off a thumb drive?

Presumably it records anything showing up on the screen being used.

Not all businesses run them, but it you work in a larger office environment they're common. They work by having a hidden client software installed on the devices that records screen shots and keystrokes and sends them to a server. There are several kinds of software that do this. Spectresoft would be one example. Running off a thumb drive wouldn't change anything. The software literally records all actions on the device.

Any business that needs to maintain PCI compliance would also be aggregating event logs from all the devices that would show what programs are being run.

The networks I ran would make it very difficult. Unregistered USB devices would get flagged for security reasons, so if you stuck your stick in one of my slots, it would send an alarm back to the admin server and shut your machine down locally with an administrator lock on it. You'd probably be escorted from the building by security as well with your belongings and be asked to leave a forwarding address for your last paycheck.

Can you provide any references? So I looked it up on wikipedia and Spectresoft appears to be a company, not a piece of software. They have multiple different kinds of monitoring software. I checked the system requirements for each of them, and they they all seem to require Windows, Mac, or Android.

So how how exactly is that software supposed to run and monitor me when I boot off a thumbdrive that does not have said software and does not run one of the required operating systems?

How do they gain administrator access to my OS on my thumbdrive?

1. Innuendo o.0

2. Would one such instance really be grounds for a dismissal? What if someone plugs in a mouse or something and doesn't know it;s verboten?
Your thumb drive will output visual info to the screen and that's what is being captured....along with any keystrokes/mouse clicks.

I think you're misunderstanding what I was talking about. If you're booting from an OS on a thumb drive than it wouldn't work. But we were talking about booting individual applications from a thumb drive, not an OS. We were talking about different use cases. Spectresoft 360 is the application I was talking about as an example. This discussion was about devices in a business environment, so my assumption was that the devices we are discussing would be domain joined.