I’m looking for a rather specific program that is capable of being put on a flash drive, and upon entering the flash drive into a computer, will automatically open web browsers, visit specified websites, and authenticate with my login information. Has anyone ever seen such a program? Ideally it’d be as automatic as possible (my job involves logging into various different machines and logging in takes a while since my password is 36 characters long) and of course, free.
This might be the first step.
http://www.downloadsquad.com/2006/06/30/auto-launch-your-usb-workspace/
Perhaps not my place to say this, and maybe you already realise it, but this sounds like a terrible idea - for the sake of saving a bit of effort typing in passwords, you’re wanting to create an object that is simultaneously highly portable (and therefore easy to lose or be stolen), and holds absolute sway over your entire digital identity.
What happens if it falls into the wrong hands?
Yeah, the implications can be bad, but I’m generally good about keeping up with flash drives… And given the nature of it, I’d probably attach the USB drive itself to my key/badge reel, making losing/forgetting it virtually a non-issue. Thanks for the sanity check though. 
Optimally the device itself would be encrypted and need a password before the program could be run.
Does the website in question use regular HTTP authentication or does it have a login form?
If it’s the former, you can simply make a shortcut that says:
start "http://username:password@www.website.com"
and add that to the USB drive’s autorun.
If it’s the latter, hmm… maybe autorun a Portable Firefox installation with the login saved? There are probably Greasemonkey scripts and/or autologin scripts if you don’t even want to push the button.
i think lastpass can be put on a usedrive, or worse case you can just install it on firefox and put the protable firefox on the drive. i think keepass also has a portable version
I use a program called PasswordVault.
It doesn’t exactly do things automatically… but it does remember URLs, usernames and passwords. You select the site you want from a list and click an icon to launch it in a browser. Then you drag and drop icons to insert passwords and usernames.
There is a free version, though I wouldn’t do without the ability of the full version to sync passwords among multiple computers/users. There are versions designed specifically for USB flash drives (Mac, Windows and Linux) and versions that will run on the desktop.
I would probably use Opera USB to do this:
It would offer you an elegant, portable and simple to use browser and password manager solution.
Opera has an excellent in-built password manager. Just save the password once for each site, and then all you need to do is click the Password icon and it will login for you with your stored password. The other advantage of using Opera USB is that you can save a session of tabs, so that whenever you launch Opera USB from any machine, the browser will open each of your websites in a separate tab, all at once. You won’t need to manually go to each wesbite.
The only limitation is that you will need to manually click on the Password icon to login for each site, but this would take less than a second per site. Other advantages are that it saves no password info on the local machine, and you can set a master password (optional) so that you only have to enter the master password once on each launch of Opera USB. If someone steals your USB device, they won’t have access to your stored passwords without knowledge of the master password.