How does play by e-mail work? Do you have to generally play an entire game in one sitting?

I ask because i want to play with my bro but we have different schedules.

You play one turn and then e-mail to the next player and he then plays a turn. So on and so on. You do not have to play a game in one sitting.

Do you e-mail through the program or do you have to exit then send a file through your own e-mail manually?

Play by Emails are games where there can be 2-8 players. PBEM’s are downloaded from your email as either a .sav file or (more of a hassle) a .zip file and then placed (usually) into the saves folder of PTW (or c3c). Of course, some of the more die hard pbem people create a folder for different type of pbems (1 vs 1’s, lots of people, etc). They do this to organize the pbems better and easier to remember when the games were sent and played. Once saved, find that folder in the PTW screen under Load Games. Once you find the save, load it . First its gonna tell you to enter your password. If it’s the first turn of the pbem, you enter a password that you will NEED TO KNOW the rest of the game. If you press enter without entering anything, it leaves the password blank meaning there will be none. After you complete your turn, you press space and save it (giving it a new name or saving over the previous save). After completing the turn and saving it, you need to open up your email (yahoo, hotmail etc) and attach the file (preferably as a .sav file but a .zip works too). And you’re done til next turn where you repeat til finished.

Do you e-mail through the program or do you have to exit then send a file through your own e-mail manually?

I believe you e-mail the "sav" file through your regular e-mail service. I have never played an PBEM game so I am not 100% sure.