How to transfer a file securely?

[Master Razor]

I want to send a project of mine to a friend but wouldn't want other people/services to read it (like online sharing, or email).
I was thinking about archiving it with a password and send it though mail. What are my other options of doing this?

[supermarrioh]

Encrypt it via Truecrypt, send it via physical mail, Share it in a VPN

[anon]

Anything involving strong end-to-end encryption should work. I would use a 7-Zip archive with a huge random password and encrypted filenames. Of course, you must find a way to transfer said password securely also.

Steganography might also be an option, depending on your needs.

[Master Razor]

That's the thing. I would be very easy to send the encrypted archive with its password in the email message body. But incredibly stupid as well..

[supermarrioh]

Encrypt the Mail? PGP and stuff? If you can verify your partners identity, that should be no problem.
Send and receive encrypted file attachments with Thunderbird / Enigmail / OpenPGP - makandropedia

[Instab]

pgp has been cracked years ago.

your best bet probably is to send the password of the encrypted file to a completely unrelated place that's using ssl. forum pm for example or something.
email, facebook and other public services are a very bad idea for anything of that kind

[leus]

I'm still for a TrueCrypt container. Maybe upload it to a filelocker. From an internet cafe if you're that paranoid.

[Master Razor]

Thanks all for your input. I'll consider TrueCrypt for now.

[supermarrioh]

Even if PGP can be cracked by some Institutions, it is still a LOT of work. Since it is open-source and nobody did Crack it in public until now, i assume its pretty secure. The risk that your machine is infected by a NSA-Virus is much higher than your PGP message will be cracked.

[shadowww]

Well, if you want something more robust, and if your friend is running Linux (and he should... actually everyone should ) then its quite trivial for him to enable SSH service on his machine. So he makes you a shell account on which you connect and transfer files via scp / sftp. All securely, via trusted, audited open source software, direct pc-to-pc transfer without relying on 3rd party hosters.

Thats how secure transfer is done propertly.

[joe1982]

With every user it's getting more and more complex. I'd say - be practical:
Encrypt the archive with a loooogng password and email it.
Give the password personally to your friend.

Relevant XKCD