Ed Felten and Randy Picker [who] point to an interesting ruling from the 6th Circuit Court of Appeals: Because people have a reasonable expectation of privacy when they communicate over e-mail, the court ruled that the government must obtain a search warrant to get your e-mail from your ISP.
The logic of the ruling is the same as the logic behind requiring a warrant for a wiretap or to search a mailed letter or package. Some legal scholars think the ruling is likely to be overturned for technical reasons, but I for one hope the legal reasoning ultimately prevails.
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I agree that most people expect privacy in their emails. However, the technology has never supported it; email has always been transmitted in clear text, wide open to every machine between its source and its destination. They all copy it, if for no other reason to transmit it. A small but significant portion of email has always been monitored, indexed and databased for various reasons - the portion only being small because there is so much email, and so little of it is of any interest.
The same is largely true of all other unencrypted internet traffic; all of your non-https web browsing can be recorded and databased by any machine between you and the web pages you download.
Making the law match people's expectations would have some advantages, but without widespread use of cross-platform open-source encrypted email, it would mean very little, as the law would be unenforceable.
On the other hand, I don't encrypt my paper mail, and I don't use a scrambler on my telephone. I have a reasonable expectation of privacy, and that's what the Constitution protects.
Or at least, what it's supposed to protect. Since we pretty much know that the NSA was tapping phone calls and reading emails without warrants, principle and practice here are not perfectly aligned, and I agree that the world would be moderately better if more people had pgp-enabled email software. I've got my email set up to handle it, but no one I correspond with signs, let alone encrypts, their mail.