>>> Of course, file by file encryption makes the encryption obvious.  Try
>>> truecrypt instead. :)
>>
>> Oh, GPG is quite capable of taking /multiple/ files and encrypting the
>> entire lot as one binary blob. So all you know is that it's encrypted,
>> and how big it is. You can't tell how many files are inside, nor what
>> their uncompressed size is...
>
> I haven't looked at GPG in a while, but didn't know it could do that.
> I'll have to have another look at it.

PGP can encrypt a bunch of files as a self-decrypting executable file. 
Then again, PGP [now] costs money. AFAIK, GPG doesn't have this feature.

> But with Truecrypt, you can encrypt the entire device and there's no
> indication of anything on it other than just random data.

Sure. There is that. In fact, I'm told there's a number of freeware 
whole-drive encryption products. They're usually applied to HDs, but I 
suppose they should apply equally to portable ones.

I also imagine that such products have to be /installed/ on any machine 
before they can be used. GPG has the advantage that it's just a single 
executable. I mean, the whole point of portable storage is to be, you 
know, /portable/. If I encrypt all my stuff and put it on a flash drive, 
and put a copy of GPG on there as well, I can decrypt on any PC I might 
visit. (Especially if I include a Linux binary as well as a Windows 
one.) If I use Truecrypt or similar, any time I visit another PC I have 
to spend time installing and configuring software before I can access my 
data.

The same advantages apply to drives with hardware encryption, of course...

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