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<v Instructor>Email header analysis.</v>
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In this lesson we're going to talk about those email headers,
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those things that are essentially hidden from view
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but contain a lot of important information.
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An email internet header
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is a record of the email servers involved
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in transferring an email message
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from the sender to a recipient.
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Let's talk a little bit about how this works
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when you send an email.
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Now, when the email is created,
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you create this on what's called a mail user agent, or MUA.
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This is essentially going to be your email program
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or Gmail, if you're running in the browser.
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We're going to use Gmail as our example here.
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Now this program is going to create your initial header
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and then it forwards that information
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over to a mail delivery agent, known as an MDA.
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This essentially goes from your email client
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to your email server, and this happens over SMTP.
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Now, that mail delivery agent is going to do some checks,
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like ensuring that the sender
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is authorized to send the message from that domain.
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This may be done using digital certificates
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or using a username and password,
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which is much more common.
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Now, once that's done, the MDA is going to check and see
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if that email can be served locally from its server.
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For example, if I'm sending an email
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from myself to my video editor,
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we both use the same email server, diontraining.com,
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and so in that case,
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the MDA would simply take that message
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and put it in their mailbox.
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But if I'm sending something to you at Gmail.com,
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it now has to transfer that to Gmail servers,
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and so the MDA passes it over to an MTA,
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which is a message transfer agent.
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This message transfer agent
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is going to route the message to the recipient
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using DNS to locate the different recipient's
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mail transfer agent to accept that message.
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Once I get it over to Gmail servers,
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or Microsoft servers,
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or whoever it is I'm sending it to,
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the MTA collects that message.
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Now, a lot of times this doesn't go
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straight from my server to the destination,
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but it routes between multiple servers
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going across the internet.
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Every time it goes to a new message transfer agent,
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that message transfer agent
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is going to add information into the email's internet header
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and this way we have a log
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of every single place this message went.
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Once it gets to an MTA, that MTA finally looks and says,
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"Ah, this is on my server,
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I'm going to send this to my person."
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And so it will send it over to the MDA,
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the mail delivery agent for its server.
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Once it does that,
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the mail delivery agent puts it into the mailbox
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and then it sits there and waits
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until you connect using something like POP3 or IMAP
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to access that message from your mailbox
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into your desktop client, the MUA,
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which, again, is our mail user agent.
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And so again, this is a simple example of how mail goes
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from a mail user agent on one end
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through the different mail delivery agents,
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through the mail transfer agents,
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and eventually back through the mail delivery agents
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to the mailbox and over to the mail user agent once more,
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where it's going to get to its destination and be read.
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So now that we've talked about how email goes
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from one place to another,
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let's talk about some of the vulnerabilities
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that could be exploited by attackers.
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First, attackers can exploit the fact
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that there are actually three sender address fields
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inside of an email, and this is something
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that is going to be something that they can exploit.
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The first one is what's known as the Display From address.
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For instance, if you get an email from my support team,
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you're going to get an email that looks like this.
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It's going to say Support &lt;support@diontraining.com&gt;.
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That is the Display From.
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Now, that doesn't actually mean anything.
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We can make that say whatever it is we want it to say
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but that is what's going to be displayed
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and that's part of the three fields that we're going to have
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as part of this internet header.
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This is what's known as the From header
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or the Display From header, and this Display From
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is going to be basically just a pretty friendly name
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with anything we want to put in there.
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Now, what attackers will often do
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is they'll change it to make it look
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like it comes from Support at Dion Training,
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even though if you looked underneath,
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it might actually be something
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like Support@diontraining.com &lt;theft@badguy.com&gt;.
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If I had that
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and you only saw the Support@diontraining part,
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that's all you're going to be seeing,
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because a lot of our mail clients only show
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the friendly part outside of the brackets
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and not what's inside the brackets.
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So you might see support@diontraining in your Gmail client
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and not the theft@badguy.com, for example.
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Now the second thing they can exploit
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is what's called the Envelope From.
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This is another from field.
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Now, the Envelope From
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is going to have various labels
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that are actually hidden from your mail client.
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This is essentially your return address.
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And so if your email is actually rejected
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by the mail transfer agent,
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it's going to go and send it back
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to where the Envelope From is.
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So this field can be anything again.
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In this case we might have something
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like support@badguy.com,
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but you'd never see it
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because it's something that's hidden
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from your display client.
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And then the third thing we have
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is what's called to Receive From/By.
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And this is a list of all the different MTAs
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that have processed this email.
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Every time an MTA, a mail transfer agent, touches this email
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as it's going through these different servers along its way,
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there is a chance that this Received By could be changed.
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Now again, this is a field
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that's not displayed to your client,
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but it is in those internet headers.
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And so if you think you have a message
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that may have been spoofed,
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you can open up your internet headers
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and see all the different Received From/Bys
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and that would tell you exactly
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which servers it's gone through
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as it's passed along the internet.
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Now, as I said, most headers are not displayed
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by your email applications by default
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but, if you see something that looks suspicious,
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you can open up those headers and start doing some analysis,
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which is what we're going to do here on a sample email.
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Now, in the example I'm going to show you here
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we've actually removed some of the fields
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to make it a little easier to read
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and we've pulled out some of the original information
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and we've put in some placeholder information,
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things like spam.foo and things like that
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as opposed to using real IP addresses or real domain names.
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The reason we did this is because, on the exam,
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this is similar to what CompTIA will do for you
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because they don't want to have anybody's real IP addresses
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or domain names shown inside of an exam simulation,
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because those IP addresses change all the time
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and it may not be malicious anymore.
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So let's take a look at this email header.
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This is what it looks like.
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Now, this is a lot of text,
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so I'm going to give you a second to read through it.
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I'm not going to read through it all right this second
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because we're going to go through it step-by-step
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as we go through our analysis.
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Now, one of the first things I'm going to look for
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when I open up an email header is
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where is the authentication results
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and what do they look like?
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So if I skip down to the fourth paragraph here
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you'll see authentication results.
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In here you'll see the Header From,
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in this case it's spam.foo,
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and this came from smtp.mailfrom identified as spam.foo.
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So this was the spam server
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or the phishing server that sent that information.
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This is a clue that this is bad.
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Now, in the real world, it wouldn't be spam.foo,
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it might be a real domain name
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but this is the area that you'd be looking at
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to see where did that message actually come from
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and what was the IP address.
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In this case, it's been abbreviated as w.x.y.z,
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because again, we don't want to use a real IP address
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that's actually owned by some real server.
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After that, we are going to read from the bottom up.
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Now as we read from the bottom up
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going from that authentication,
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we are going to see all the servers it's gone through.
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Now the first one we see here
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is it went through openrelay.foo,
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which is our spam server here,
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and again, we have an IP address of w.x.y.z.
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Now as we look at this,
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we're going to be able to see exactly where it came from
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and that openrelay was somebody
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that was sending spam through that server.
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A server that's been taken over and used by a bad guy
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is what's known as an open relay,
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which is why we have that placeholder here.
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Now, this field is showing us the SMTP server
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where the message was actually originated from.
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In this case it came from openrelay.foo.
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Now, if I went and looked at openrelay.foo,
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I might look it up and get some information about it,
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do some open source intelligence and figure out,
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is this a known spam agent?
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And if it is, it may be found on some blacklist,
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and if so, we might want to add it to our blacklist as well,
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so we're not getting that spam inside our systems either.
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Now, the next thing I want to look at
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is how we can do a much cleaner and easier way
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of looking at this information.
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Well, one of the things
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is that this information is a lot of text
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and it's pretty heavy to look through,
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but there are some tools out there that you can use.
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One of them is called testconnectivity.microsoft.com,
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and if you go there, you'll find the tool
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called the Message Header Analysis.
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You can take your message header
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and paste it into the top block, like I've done here,
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hit Analyze headers, and it will actually break it down
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into areas for you to see in a much easier format.
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So for example, here you can see
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the first hop was openrelay.foo,
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and then at the bottom we can see
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that authentication results I showed you before,
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smtp.mailfrom=spam.foo
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and header.from=spam.foo.
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Both of those are the pieces of information we wanted
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as we started looking through the different headers
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and we wanted to see where it came from.
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By using something like this,
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it is a lot quicker and easier
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for you to identify things quickly
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as you're looking through them
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and identify exactly what the delays were in between
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and how long things sat.
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For instance, if a message sat someplace with a long delay
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that could have been time that an attacker was using
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to modify that message,
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and so it'd be something you'd want to look at as well.
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Now let's take a look at the actual message itself
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as we go through some of the rest of the headers here.
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As we continue down the header,
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we'll see some more information,
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for instance, the subject, in this case,
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"Your account is blocked by the administrator".
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That's a pretty alarming subject
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and it might get somebody's attention to open up
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and click that email and click a link inside of it.
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Then we can see the content inside of it.
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We can see different content type, the date,
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the MIME version, the From account, the To account,
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and the Return-Path.
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Let's take a look at that From account
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a little bit more in depth.
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Now look at that, it says:
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Gmail Accounts &lt;spammer@spam.foo&gt;.
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So again, remember that From header
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is just what we want it to display.
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I could type anything I want in there
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and so in this case, we're saying
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this is from Gmail Accounts, even though it's not.
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It's from spammer@spam.foo.
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And then we have the return path.
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This is where the email actually goes back to
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if there's a problem delivering it.
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And in this case you could see it's spammer@spam.foo,
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which is the real email address.
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Now, again, I can change that From account
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to anything I want,
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but the return path has to be the right one,
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otherwise the MTA will not deliver the messages.
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All right, let's look at the next part of the header.
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Here I have what are called the X headers
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and you'll see X-MS-Exchange,
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X-MS-Office, X-Sender, X-SID,
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bunch of different stuff here.
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Now, X headers indicate custom headers
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that are controlled by the SMTP server administrator.
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So you'll notice in my example here,
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we have things like MS Exchange, MS Office 365,
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Microsoft Anti-Spam.
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These are all things controlled by that server
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and, in the example I showed you earlier on the diagram,
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we were sending our information
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to a Microsoft Exchange server
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that was run by the Microsoft Corporation
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and that's who's controlling these headers.
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So if I look at that,
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you might see one here that has X-SID-PRA.
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Now, X-SID-PRA is giving me spammer@spam.foo again.
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Again, this is some information that helps us
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as we are going through and figuring out spam
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and it's something that we can actually use
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as part of our analysis
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by setting up these X headers
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to be able to document different pieces of information.
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This is one that is used by Microsoft 365
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as part of their anti-spam efforts.
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So I hope you enjoyed this quick walkthrough
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of the email's internet header
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as we looked at some of the basic information in it.
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For the exam, you should be able
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to read and pull out different pieces of information
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if you're given an email header.
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Now, later in this section
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we are going to go into our lab environment
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and I'm going to walk through some more headers with you
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so you can get comfortable with this concept.
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But in this lesson,
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I just wanted to give you the introduction
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and so you could understand
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how to read the different parts of it.
