Vista - Encrypting for Dummies

I am getting a new 16G Flash Drive today in the mail from Newegg. I want to use this as a means to keep very important personal documents on it to transport easily with me.

-- What is the best way to encrypt them incase I ever (god forbid) lose this drive?

-- When you encrypt files, how would it work if I want to open a file between different locations?

I am sure I have other questions, but those are the two major ones that come to mind right now....

Look here:
Free PGP Encryption Utilities downloads. Only freeware

If there THAT important to you why not get a https://www.ironkey.com/ USB key with built in HARDWARE security. No use mucking around if youre serious, but if youre not serious, well there are plenty easilly cracked software solutions out there.

Built in security on it. I actually have a few these for work and personal files, they work great.

try turecypt its free, stable, many options, easy to use, good documnetation,
you cant go wrong

even though the file is encrypted it is still handeld by the system as a normal file

With truecrypt, youre SOL if both systems dont run it.

example:

System A has true crypt, so I encrypt USB drive.

System B does not, I insert truecrypt encrypted drive...I am screwed.

Its not truely portable, while https://www.ironkey.com/ is truely portable. Any software solution wont be truely portable unless every system you want to read the USB stick on has that software.

Wow, those drives are not cheap! lol....

The reason these documents are important is that they have my SSN on them. That's all. I just really want an encryption program that I can install on my computer at work and on my home pc (i do great work while i'm "working").

I am just interested in the best program that I can get to install on both PC's.

No, there not cheap, but they are the best of breed also. I hjave a 8GB personal I bought and a 8GB enterprise for work.

1Gig for $80.... I can afford it but it's not really worth it. Thanks though for informing me that those drives exist. One day I might need one for something. But until then I'm happy with my 16Gigs "Diesel" drive I got for $35.

For any program I get to encrypt my files, as long as I have that program on the PC I am working on, will it automatically decrypt it? or are things password protected? how does that work? and again, I ask what is the best program out there for it? Free or not does not matter. Truecrypt?

(just re-read this post.... didn't mean to sound like a dick if I came acrossed that way at all)

So Truecrypt?

is there anything I should know about using encryption software before I attempt anything? I have never done this before