Necessity of GPG when using SSL

Henry Hertz Hobbit hhhobbit7 at
Fri Feb 24 12:06:17 CET 2006

Benjamin Esham <bdesham at> wrote:

>On Feb 22, 2006, at 6:22 AM, Janusz A. Urbanowicz wrote:
>> And there is really no point in ecryptiong the whole access since the
>> contents, the emails usually travel the rest of the net unencrypted.
>But wouldn't it be much easier for an attacker to intercept all of
>your e-mail by listening in on an unencrypted webmail session than by
>trying to intercept each e-mail individually somewhere else?  I think
>there certainly is a benefit to having SSL-encrypted webmail for
>exactly that reason:  less determined attackers will not have access
>to the plaintext of the messages. (Although granted, it would be kind
>of foolish to depend upon SSL webmail if the messages are sent in
>plain text.)

Last then first.  Generally, it is very difficult to intercept email
en-transit.  That was not always the case.  There was a time when you
had hubs and you could listen in to everything on a LAN.  Those days are
gone with switches (multi-port bridges) making it very difficult to
listen in on communications since the only traffic you see now at the
LAN level is the broadcast traffic.  There are some switches and routers
that have a listening port, and this is what the FBI and others want,
but they are the exception, not the rule.  Once packets start hitting
the WAN pipes, the torrent of packets you have to sift through becomes
almost impossible to manage, even if you know the person's WAN IP
address, and it is just that - a person.  If you have several hundred
people sharing that WAN IP address, then en-transit capturing has to be
done at the LAN level.  How do you say this packet from WAN IP address is Bob's and not Bill's when up to 100 people share that WAN
IP address?  You have to go inside the firewall where that IP address is
and find out on the LAN.  Lo and behold, when you do that, they are
using DHCP, so you then have to know their MAC address (which used to be
something you couldn't change, but now with MS Windows you can change
it).  So let's just go to Bob's machine and put something on it instead.
And that is usually exactly what is done.

Where your email is most easily compromised is on the mail server.  There
it sits until you start to pull it down.  SSL isn't even a factor.  All SSL does is secure the transmission, not the data at the end points.  In fact,
a hacker can pull down your email using SSL to cover their tracks - and
that is usually exactly what they do. It is usually pretty easily done
too, since ALL of the messages are usually in just one file.  They just
have to suck down that one file and now they have ALL of your messages.
Now, if the email on the server is in plain-text, how secure is that?
On the other hand, if it is encrypted with some OpenPGP package like
GnuPG with strong encryption, how secure is that?  Pretty darn secure.
So the hacker pulls down your file. Whoopity doo.  He gets to read all
that crappy spam in plain text, but the juicy email messages that contain
your financial information is encrypted.

So, I repeat - SSL is not good enough unless all of your messages don't
convey financial information or anything else important.  If they are
important, use GnuPG or other strong end-point encryption and the only
thing you have to watch for now are those pesky key loggers.  But even
then if they get your passphrase, they still need your keyring, but if 
they have a keylogger working for them, then they probably have all your
GnuPG DB files.


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