What is the safest way to transfer important tax documents?

Safe in terms of them getting there or safe in terms of other people not being able to look at them?

I’d vote for FedEx.

Email is not safe in terms of having someone else read your documents, unless you use a separate encryption on the attachment. Anyone can easily access your email unless it is encrypted. Snail mail is fairly safe, but I would say a secure download would be the safest, assuming it uses the proper encryption standards.

@andrew Both, I guess. Fax will be ok if I stand there and fax them directly and the person collects them instantly, but I worry about the transmission or someone else picking up the documents.

I guess I should say this applies to all important documents. What is the most secure, but rapid method? The secure download seems insecure to me in that it is housed on someone’s cloud computer somewhere. Who, other than me, can access that?

Certified U.S. Mail.

Okay, now I’m curious, what kind of super-secret documents do you need to send?

Fed Ex, mail, scan and email. The odds of somebody snooping your mail are infinitesimally low. Unless you gave somebody else the password. Or you are a high-profile criminal. Or you are sending it physically to an office, where mail is routinely opened by clerks/secretaries. And if they work with tax documents, they are unlikely to be unprofessional enough to actually read the contents.

Or you could allow the other party to connect to your computer via Remote Desktop or VPN and let them download it.

A Windows 7 or Vista VPN is actually really simple and quick to set up.
http://www.publicvpn.com/support/Vista.php

If you have a web site, call the other person with a link, post the document, delete it as soon as they have downloaded.

@bob_ Nothing too secret. Just documents with enough information for an identity thief to have a field day.

Scan to PDF with password protection in place.. then ZIP it with another password protection, then email the ZIP file.

I agree with scan to PDF with password protection.

Safest would probably be carrying them yourself in a locked briefcase chained to your wrist and with an armed escort. Maybe that’s too safe…

If you want to be sure they get it and you use email, you’ll want to request a read receipt on the email.

Personally, I turn off “Send read reciepts” when I set up mail programs.

The Post Office actually provides confirmed email, but I’ve never heard of anyone using it.

“The USPS Electronic Postmark® (EPM)* is an auditable time-and-date stamp service offered by authorized service providers, under license by the United States Postal Service. The EPM can be used to verify the authenticity of a document or file sent electronically, and provides trusted proof of content as of a specific point in time.”

http://www.usps.com/electronicpostmark/welcome.htm

Upload ‘em to Fluther.