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This is a simple Secret Santa organizer which uses JavaMail and GMail SMTP to send out Santa-Assignments.  I designed it so that I could simply type a bunch of information into a text file and have it automatically send out the emails rather than me being omniscient as to who's getting what, including who's gifting me.
 
The JAR is self-executing and contains the JavaMail API inherently, so just put it on your desktop and double click it.  It will then ask you for a file which contains the configuration information.  The configuration should look something like this:
 
---File Begin---
[gmail address of organizer]
[gmail password of organizer]
[Rules typed out on one line]
[Santa 1's Name]
[Santa 1's Email (gmail or otherwise)]
[Santa 1's Description (can include their t-shirt size, or other important info)]
[Santa 1's Mailing Address (put NA if your gift exchange will be done locally)]
[Santa 2's Name]
[Santa 2's Email]
[Santa 2's Description]
[Santa 2's Mailing Address]
....
---File End---
 
Only the organizer has to be using Gmail; the rest of the emails can be any ISP or provider in the world.  Also, it is important to note that if the organizer wants to particpate he/she must include t  Once you click okay, it'll go through and map the Santa's other Santa's in the list and email them individually.  At the end you should get a dialog box stating that the emails have been successfully sent.
 
The program is very basic right now, so double-check and then triple-check your configuration file to make sure it's formatted properly.  If it's not then some emails might go out while others fail and you thus would have to re-send out the assignments.