I've been thinking a fair bit about the EFF's lawsuit against AT&T. According to court papers and press reports, AT&T is giving the NSA a direct network tap at multiple locations around the country, giving the US government access to all unencrypted email/IM conversations and web traffic that flow through AT&T's network. It's probably fair to assume that a few other backbone providers are also doing the same thing.
Consider the following situation:
Alice sends an email from her home computer (connected via Verizon DSL Connection) to her friend Bob, who checks his email from his desktop computer at work. Alice uses Hotmail, and Bob uses his company's email servers.
Alice's web connection to hotmail will most likely flow across AT&T's backbone, and if it doesn't, it'll cross one of the other Big Boys, like Level 3. Once Alice has created her email, it'll flow from Microsoft's email servers to Bob's employer's email server - unencrypted, again, probably over one of the major backbones, until it reaches Bob's desk.
There will be at least a couple chances for the NSA to sniff this.
What if Alice sends an email to her pal Charlie, who also uses hotmail?
Well, again, the spooks will have a chance to watch Alice construct the email, and then will be able to see Charlie login to hotmail and read it. Key to note here, is that since the email stays within Hotmail's network, it never has to flow across the Internet to go from Alice to Charlie.
Which brings me to the subject of gmail.
Google is nice enough to allow SSL encrypted sessions. Whereas Yahoo and Hotmail merely allow you to login via SSL (just to stop a passive network sniffer learning your email password), google allows the entire session to remain encrypted. Thus, any interaction between a user at their home computer, and Google's gmail servers remains secret, providing the user changes the url to be https://
Let us now consider a situation where Alice and Charlie each have gmail accounts, and each login via ssl. Alice's connection to google is encrypted, the email flows from one gmail user to another, so it never leaves google's network as it is transmitted from Alice's outbox to Charlie's inbox, and then Charlie's connection to Google is SSL encrypted, so the contents of his email is not revealed to anyone watching his packets cross the backbone.
Right now, very few of gmail's users are using SSL. It us turned off by default (mainly for performance reasons, I'm guessing. 10 million users all requiring an SSL handshake is expensive in processing power).
As gmail's user base grows, and if their users can be convinced to embrace SSL, the NSA's wholesale data slurping from the backbone will increasingly become less useful.
"If we all use encrypted email (PGP/GPG), we won't have this problem" - this is the very true. However, I cannot convince my less technically savvy friends/relatives to use PGP. It has far too many usability problems - still.
However, most of my friends already use gmail - due to the way accounts were given out in the early days, gmail has a very geeky user base. All I need to do now, is to convince them to use SSL... Which is where the Customize Google firefox extension comes in useful.
Customize Google is mainly used to screen out google's advertising - both in gmail, and in the "ads by goooogle" that you see everywhere on the web. I typically install this on the computers of most of my less tech savvy friends. In addition to blocking out ads, Customize Google also turns on SSL for all gmail/google calendar sessions, without requiring that the user do any fiddling themselves. Problem solved!
This only stops the massive sniffing of data currently done by the US government of backbone traffic. This in no way protects you from the feds asking Google for the contents of your email - either by presenting a warrant, or more likely (since it doesn't involve asking a judge), a national security letter. I have good reason to believe that the FBI did this to me - but that's beside the point. This at least requires them to know who you are, and to be interested in you - whereas under the current NSA sniffing scheme, they can watch all email flow by, and analyze it without knowing who they're interested in spying on.