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I am looking to share sensitive documents but I don't want to send them over email. Because the document is visual, I don't care to send it via FAX either, since it won't reproduce well.

Is there a well known, reliable application that will allow two parties to do this easily?

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Hm, you're not keen on them installing software (7z) and you don't want a website. FedEx? – hyperslug Jul 25 '10 at 1:45
I didn't way I don't want to use a website, I said I don't have a website. – Rhubarb Jul 25 '10 at 2:51
I think the question needs to be edited then, it reads as if you don't want to use a website. Maybe edit to: ...", without having a web server of my own?" – Robert S Ciaccio Jul 25 '10 at 3:40
thanks for the edit gnoupi, and i love the avatar :P – Robert S Ciaccio Aug 1 '10 at 20:24
up vote 6 down vote accepted

When you say without a website, I'm assuming you mean you don't have a website rather than don't want to use a website. If that is correct, dropbox might work well for you - they have an application, but you can also share documents via their web interface without installing the application. It's free to use for smaller file sizes, and prices are reasonable for more gigabytes of files.

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Quite frankly, if the documents are sensitive, I wouldn't trust a third party server... You're just handling your files to another party. – Andrew Moore Jul 25 '10 at 4:19
+agreed... however, he doesn't appear to be TOO concerned about the sensitivity of the documents if he doesn't want to have the other party install 7zip so they can be encrypted :) – Robert S Ciaccio Jul 25 '10 at 6:36
@Andrew Very good point. Depending on how sensitive the documents are it would be best to setup his own file sharing system. – direct00 Jul 27 '10 at 1:49

What's wrong with email?

Zip/7z the documents with a strong password and AES-256. Attach the zip to your email, and use the phone to transmit the password...

If someone intercepts your mail, he cannot read the documents.
If someone eavesdrops on your phone, he doesn't have the documents.

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Good one. Not sure about asking the party to install 7z. I have it though. – Rhubarb Jul 25 '10 at 0:55
Then just a regular AES-256 protected zip should do the trick. – Andrew Moore Jul 25 '10 at 3:04
If you can't ask the party to install something standard like 7z, you can't rely on such party do share sensitive data in first place. It all depends on how sensitive your data is. – user39559 Sep 14 '10 at 13:31
I would think 7-zip supports creating a "self-extracting" file, which will prompt the user for a passphrase. – TOOGAM Apr 8 at 5:39
@AndrewMoore: "What's wrong with email?" Plenty, for this task. Non-encrypted SMTP has been standard for a long time. E-Mail is often backed up. Unnecessarily large E-Mails can overburden systems like backups, malware scans, and maybe even E-Mail delivery (if staff designed the systems for messages, not large files). These days, 10KB files usually work, but multi-gigabyte files may have unintended (bad) consequences. The original question didn't specify a file size, so small sizes is not currently a safe assumption. A more sensible way is using a system designed for the intended task. – TOOGAM Apr 8 at 5:45

There are any number of options, but if you want something that's relatively secure and fairly simple for a non-technical user to use then I suggest using Opera and it's Unite feature.

All you need do is install the Opera browser on the two machines you want to share the information between.

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Good suggestion, are there any solutions that require only a website? I am not keen on asking the other party to install more software now that I think about it. – Rhubarb Jul 24 '10 at 22:18

I believe is what you're looking for.

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If you need to encrypt docs without the other party having an encryption package, why not use something like PGP and encrypt to a self decrypting archive. Exchange the passphrase by phone, SMS, email or other mechanism, then you can pass the data anyway you like - Dropbox or email or whatever, and all the other party has to do is use the passphrase to access your documents.

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