how secure is email
hi everyone leo notenboom here for
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dive right into the question my boss
requires the emailing of some sensitive
information on a regular basis i've
spoken with my boss and co-workers about
all of us using an encrypted email
system but no one seems to think there
is a significant threat or danger out
there to require
these extra steps in security
can you offer any data to help me
convince them that this is a good idea
well no i don't have any hard data to
say one way or the other
i do know that email encryption turns
out to be surprisingly difficult
but on the other hand the email system
was designed in a simpler time and
data privacy security
hiding your data and sending sensitive
information via email
honestly wasn't really baked in and that
means that adding it as an afterthought
as we want to do
can be kind of problematic
the risk honestly varies to too much
depending on who's communicating what
they're communicating what systems they
happen to be using and of all things the
path between the two communicants
so let's think first about what i call
the practical risk
most people
have an over inflated sense of risk for
things that they don't understand
i get it it makes total sense certainly
from an evolutionary point of view but
even from a technological point of view
it's certainly safer to assume the worst
for something that you don't understand
and lord knows email is incredibly
difficult to understand
not the how do i send and receive emails
that has its own level of complexity but
the behind the curtains magic that
happens once you press send
how does that message make it from point
a to point b
you or i probably don't have all the
details
and that's fine you shouldn't have to
know
but when it comes to understanding the
security of your email
it's really worth understanding just how
many different places along the way
your email might be exposed
the bottom line is that anybody that has
access to the network the networking
equipment your mail servers or the pcs
across which your message transmits
has an opportunity to actually take a
look at the message
that might include for example
anyone with access to your machine so if
you have somebody else that can sign
into your machine or can use your
machine it's a good chance they can see
the email you've sent
malware that's just sort of an
all-encompassing term for any malicious
software that might land on your machine
and since i've said many times malware
can do anything
one of those anythings is let's have a
look at this guy's mail
other machines on your network
maybe and i have to say maybe because
this is where it really starts to get
down into the technical
rats nest of issues right depending on
how your email is transmitted from your
machine out of your network to your
router
it's possible that some other machines
on your network could listen in they
could see what's transmitting across the
wire even if they're not involved in the
conversation it's very very similar to a
wi-fi hotspot
which by definition anybody within range
can listen in to the radio communication
that is the transmission of your email
to your email server your isp your isp i
mean they're providing you with this
service almost by definition that means
they have to be able to see what it is
you're doing
and they can
your email provider again same story
they have to be able to understand your
email in order to be able to handle it
to deal with it to send it on to where
it's supposed to go
now
all of a sudden we're talking about you
know what the other side of this happens
too so
your recipient's isp
your recipient's email provider your
recipients network other machines on the
recipient's network
malware on your recipient's machine and
of course anybody that might have access
to your recipient's machine
all of these are i'll just call them
opportunities
for an individual or an entity to have a
look at the messages that are being
transmitted between you and your
recipient
now that sounds really scary because
honestly there's a lot of people
involved there's a lot of places
where things can be exposed
i don't believe it's any cause for panic
lord knows i rely on email every single
day
and i don't panic i know how many steps
to go through but what i also know is
that
these servers these services the people
who might be interested they're too busy
i've said before that you and i just
aren't that interesting nobody's out
there scanning what we do
with the hopes of finding out something
about us
could they of course there's lots of
things that could happen but do they is
the question and my sense is my very
strong sense after having done this now
for decades and transmitted a lot of
honestly very sensitive information via
email
is that in general
no
it's just not something that i spend a
lot of worry about
the real risks
the risks that i want you to focus on
the most
are at what i call the end points
you and your machine and your recipient
and their machine
getting things secure in between those
two points we'll talk about that in a
minute
but making sure that your machine
doesn't have malware making sure that
your machine
your email account is configured
properly that your machine is locked
that individuals can't just walk up to
it and view your email those are the
kinds of things that
probably matter the most and bonus
they're in your control those are the
kinds of things you do have control over
now what if
what if
you are quote unquote that interesting
right i've said before you and i aren't
that interesting but but but what if we
are right what if for some reason we are
well then unfortunately the answer boils
down to
encryption
that's where things start to get
really really confusing
and unfortunately because there is i
don't want to call it a lack of
standards because there are standards
but there are three standards
the most common one no encryption at all
the next one is probably
s mime and the next one is probably pgp
yes you can use you already are using
probably the unencrypted one you can
look into encrypted services but the
problem is both you and your recipient
must and i have to say must be using the
same encrypted service in order for
email encryption to work
that's typically not particularly
practical
the fourth standard and it's the one
that a lot of attorneys seem to take
don't use email at all use a telephone
call use something other than email
something where what you're saying isn't
being recorded and more importantly what
you're saying isn't necessarily being
intercepted now there are some what i'll
call very pragmatic things that we
probably don't even realize are
alternatives to email
for example my online brokerage
they will send me an email but the email
itself will have no sensitive
information in it it will say hey
there's information in your account
go over log into it and then we can show
you what that sensitive information is
then i go to their website their https
configured website
and i view the secure message the the
information about my accounts the
whatever
that conversation between my browser and
their website
is point to point
there are
no intermediaries examining the data
because a the data is encrypted that's
what https is all about only i can see
it and only the brokerage can see it
anybody in the middle anybody who can
successfully intercept the communication
will see only encrypted garbage
again endpoints matter if you've got
malware on your machine well yeah i
could see the unencrypted data but
that's something that's in your control
choosing to use an https connection to
get messages from a provider or from
a brokerage or a bank or a health care
provider
that's the secure alternative to email
email serves only as a completely open
and unencrypted notification that you've
got something to look at and then you've
got a secure way to go and examine the
message that's being sent to you
now i do
want to talk about encryption in email
like i said there are multiple different
approaches
i'm not going to get into things like
mime or pgp because honestly
it's a lot more work than it's worth
and for the average user for sure and
there are simple conceptually simpler
alternatives that don't rely necessarily
on you know i could only send it to this
person because he's using this kind of
encryption i can only send it to that
person because they're using that kind
of encryption
the approach that i take when i'm backed
into a corner and i have to send an
encrypted message using my normal email
account is i will write my message as a
document a word document a plain text
document whatever
i will then zip it using 7zip or some
other zip utility with a password that
password encrypts the data and i will
then email that zip file as an
attachment to my recipient i'll then
make sure that they also get the
password but
usually through a different
communication path be it a telephone
call a text message an instant message
using some other service whatever but
the point is that the encrypted data
travels alone and encrypted
and the password travels separately so
that the recipient and only the
recipient can then decrypt the message
and read it
now there is one
more solution and honestly this is
probably the solution i would find
myself end up using more often these
days as it turns out i have a protonmail
account
protonmail
by definition
advertises itself as a completely
encrypted email system
which is
true to a point
it's true in the sense that when you
send email from your protonmail account
to another protonmail account
that email is encrypted it's stored
encrypted the only time it's ever
decrypted is when you're writing it or
when they're reading it protonmail can't
even see the message all they can see is
the encrypted blob which is pretty much
exactly how you want encrypted mail to
work
but what if you want to send to somebody
that doesn't have a protonmail account
well they kind of do a couple of the
combination of things that i've just
been talking about
if you send an encrypted message to a
non-proton mail email account
what gets sent to the recipient is not
the message
what gets sent to the recipient
is a message that says
you've got mail you've got a message
here's a link to that message and that
link goes to
protonmail.com
that then allows protonmail to use an
https connection to make sure that the
conversation between your recipient
and the protonmail servers are secure
and
then your recipient still has to give
the password for your encrypted mail
which you've again given to them via
some other mechanism that will allow
protonmail to then decrypt the message
in order for them to be able to see it
but they're watching it they're looking
at it they're reading it on a web page
they're not reading it via email all
they got via email was a notification
there was a message the message itself
is displayed on a secure website owned
operated and secured by protonmail and
they can reply they can actually hit
reply uh compose a message again all in
the web interface and send it back to
you usually with the same password or
maybe an opportunity to set up another
one but the bottom line is that the
encrypted message actually is never sent
via email other than within the
protonmail ecosystem so that's probably
the approach that i would take these
days if
even setting up you know a zip file
is a little bit too much for you and or
your recipient
i hope that helps like i said exactly
whether or not
encryption is really needed in email
that's something that i can't answer
because it varies much too much on the
specifics of the situation
and what i'll call the cost of failure
in other words just how bad is it really
if you're somebody actually does end up
looking at this email
but
there are alternatives there are ways to
get the message communicated securely
none of them
are as streamlined or as simple as we
might want them to be but at least they
exist
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i'm leo notenboom this is askleo.com
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