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I've recently gotten a new job on the other side of the planet. Exciting stuff.

But then I need to concern myself with my data. My computer set-up is as follows:

  • Home Server
    • Windows Server HDD
    • A HDD that serves as a repository for all of my ISOs and large important downloads
    • Another HDD that holds Hyper-V VM VHDs
    • Another HDD that serves as the "data" drive for a Hyper-V VM that runs MS DPM
    • Another HDD that a Hyper-V VM running Exchange 2010 uses to store the EDB
  • Desktop
    • System HDD
    • User profile HDD (I modified my Windows installation so all the profiles are D:\Users)
    • My old computer's HDD with documents from 1996-2008 stored on it (I need to make backups!)
  • Laptop
    • Single 256GB SSD

That's a lot of HDDs.

My problem is that my job is in a country with a bit of a repressive regime and there is no uncertainty in my mind that any computers in my company-provided air-freight crate will have their HDDs examined, so I've decided to remove all HDDs from my computers before they go into shipping (except for my laptop, which will be in my carry-on).

This leaves at least 8 3.5" drives, roughly 5TB of data, that I need to sneak into the country.

I'm paranoid about my data because it's almost everything to me, including my personal diary, and I also frequent on sites like 4chan and Fark so I have a lot of "unsavoury" (but far from illegal!) content on my drives that I'd rather not part with. I think I also have stuff like The Anarchist Cookbook on my drives too - I'd rather not answer questions about those, of course.

One possibility I thought of is consolidating as much data onto a single drive, for example I could mount my desktop computer's HDDs on my server and copy their contents onto a huge 2TB drive and leave only the System HDD (which contains no confidential or personal information). I could do the same with the server.

I could wipe the DPM backup drive and leave it in the server, which means I'd only need to smuggle two 3.5" drives: my Exchange VM server's dedicated HDD, and "the drive with everything on it" - all of the drives left in shipping are just system disks. I could fit the 3.5" drives into fairly compact external HDD caddies that go with my laptop.

Obviously I'd then make another backup of that "one drive" and leave it with a trusted friend at home.

Does that sound like a sound strategy to everyone?

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closed as not constructive by Nifle, Mokubai, Canadian Luke, Indrek, Kez Sep 9 '12 at 15:26

As it currently stands, this question is not a good fit for our Q&A format. We expect answers to be supported by facts, references, or expertise, but this question will likely solicit debate, arguments, polling, or extended discussion. If you feel that this question can be improved and possibly reopened, visit the help center for guidance.If this question can be reworded to fit the rules in the help center, please edit the question.

Encrypt everything. – Nifle Sep 7 '12 at 22:18
That's not really an option for my system drives, and it seems like more hassle compared to just moving data around. I did encrypt my drives in the past, but I lost the password or the data on the disks themselves got corrupted and I lost a lot of data that way. – Dai Sep 7 '12 at 22:23
-1 This question could have been asked in one or two sentences. – Baarn Sep 7 '12 at 22:31
If you think encrypting is to much hassle then you're not really that concerned about your privacy. – Nifle Sep 7 '12 at 23:25
@Informaficker: edit it? – Mechanical snail Sep 8 '12 at 2:14

If you are so paranoid:

  • Compress, encrypt, burn most important data on DVD's
  • Encrypt all HDD's using proper software for example TrueCrypt
  • Buy external drive (~$100 2TB), encode, compress and copy most important data

But this is not safe way to go! Please read this:

Man jailed over computer password refusal

Safer approach:

Compress and encrypt everyting. Give it to your best friend on some hard drive. When you get abroad ask friend to open FTP server for you for 3-4 days. Download data.

Responding to your comment: You can make an image of your system disk (using tools like Norton Ghost) and then restore it when you arrive.

share|improve this answer
That works fine for my data, but not system drives. I'd rather not have to reinstall everything. – Dai Sep 7 '12 at 22:23
It totally makes sense to encode (what? I guess you mean encrypt) everything and then transmit it over an unsecure channel like FTP… – Baarn Sep 7 '12 at 22:25
@Informaficker This why you encrypt data. If you are even more paranoid use SFTP :D – Peter Sep 7 '12 at 22:26
Well transmitting the encrypted file actually does make sense. Sorry, I always expect people to do it the stupidest way possible :) (And FTP always is backwards technology for me, somewhat like telnet for files) – Baarn Sep 7 '12 at 22:29
@David - Image your system disks then, then compress/encrypt – Logman Sep 7 '12 at 22:30

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