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authorAldo Cortesi <aldo@nullcube.com>2014-01-22 13:33:02 +1300
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-
-
-Mitmproxy is an enormously flexible tool. Knowing exactly how the proxying
-process works will help you deploy it creatively, and take into account its
-fundamental assumptions and how to work around them. This document explains
-mitmproxy's proxy mechanism in detail, starting with the simplest unencrypted
-explicit proxying, and working up to the most complicated interaction -
-transparent proxying of SSL-protected traffic[^ssl] in the presence of
-[SNI](http://en.wikipedia.org/wiki/Server_Name_Indication).
-
-
-<div class="page-header">
- <h1>Explicit HTTP</h1>
-</div>
-
-Configuring the client to use mitmproxy as an explicit proxy is the simplest
-and most reliable way to intercept traffic. The proxy protocol is codified in
-the [HTTP RFC](http://www.ietf.org/rfc/rfc2068.txt), so the behaviour of both
-the client and the server is well defined, and usually reliable. In the
-simplest possible interaction with mitmproxy, a client connects directly to the
-proxy, and makes a request that looks like this:
-
-<pre>GET http://example.com/index.html HTTP/1.1</pre>
-
-This is a proxy GET request - an extended form of the vanilla HTTP GET request
-that includes a schema and host specification, and it includes all the
-information mitmproxy needs to proceed.
-
-<img src="explicit.png"/>
-
-<table class="table">
- <tbody>
- <tr>
-
- <td><b>1</b></td>
-
- <td>The client connects to the proxy and makes a request.</td>
-
- </tr>
-
- <tr>
-
- <td><b>2</b></td>
-
- <td>Mitmproxy connects to the upstream server and simply forwards
- the request on.</td>
-
- </tr>
- </tbody>
-</table>
-
-
-<div class="page-header">
- <h1>Explicit HTTPS</h1>
-</div>
-
-The process for an explicitly proxied HTTPS connection is quite different. The
-client connects to the proxy and makes a request that looks like this:
-
-<pre>CONNECT example.com:443 HTTP/1.1</pre>
-
-A conventional proxy can neither view nor manipulate an SSL-encrypted data
-stream, so a CONNECT request simply asks the proxy to open a pipe between the
-client and server. The proxy here is just a facilitator - it blindly forwards
-data in both directions without knowing anything about the contents. The
-negotiation of the SSL connection happens over this pipe, and the subsequent
-flow of requests and responses are completely opaque to the proxy.
-
-## The MITM in mitmproxy
-
-This is where mitmproxy's fundamental trick comes into play. The MITM in its
-name stands for Man-In-The-Middle - a reference to the process we use to
-intercept and interfere with these theoretically opaque data streams. The basic
-idea is to pretend to be the server to the client, and pretend to be the client
-to the server, while we sit in the middle decoding traffic from both sides. The
-tricky part is that the [Certificate
-Authority](http://en.wikipedia.org/wiki/Certificate_authority) system is
-designed to prevent exactly this attack, by allowing a trusted third-party to
-cryptographically sign a server's SSL certificates to verify that they are
-legit. If this signature doesn't match or is from a non-trusted party, a secure
-client will simply drop the connection and refuse to proceed. Despite the many
-shortcomings of the CA system as it exists today, this is usually fatal to
-attempts to MITM an SSL connection for analysis. Our answer to this conundrum
-is to become a trusted Certificate Authority ourselves. Mitmproxy includes a
-full CA implementation that generates interception certificates on the fly. To
-get the client to trust these certificates, we [register mitmproxy as a trusted
-CA with the device manually](@!urlTo("ssl.html")!@).
-
-## Complication 1: What's the remote hostname?
-
-To proceed with this plan, we need to know the domain name to use in the
-interception certificate - the client will verify that the certificate is for
-the domain it's connecting to, and abort if this is not the case. At first
-blush, it seems that the CONNECT request above gives us all we need - in this
-example, both of these values are "example.com". But what if the client had
-initiated the connection as follows:
-
-<pre>CONNECT 10.1.1.1:443 HTTP/1.1</pre>
-
-Using the IP address is perfectly legitimate because it gives us enough
-information to initiate the pipe, even though it doesn't reveal the remote
-hostname.
-
-Mitmproxy has a cunning mechanism that smooths this over - [upstream
-certificate sniffing](@!urlTo("features/upstreamcerts.html")!@). As soon as we
-see the CONNECT request, we pause the client part of the conversation, and
-initiate a simultaneous connection to the server. We complete the SSL handshake
-with the server, and inspect the certificates it used. Now, we use the Common
-Name in the upstream SSL certificates to generate the dummy certificate for the
-client. Voila, we have the correct hostname to present to the client, even if
-it was never specified.
-
-
-## Complication 2: Subject Alternative Name
-
-Enter the next complication. Sometimes, the certificate Common Name is not, in
-fact, the hostname that the client is connecting to. This is because of the
-optional [Subject Alternative
-Name](http://en.wikipedia.org/wiki/SubjectAltName) field in the SSL certificate
-that allows an arbitrary number of alternative domains to be specified. If the
-expected domain matches any of these, the client will proceed, even though the
-domain doesn't match the certificate Common Name. The answer here is simple:
-when extract the CN from the upstream cert, we also extract the SANs, and add
-them to the generated dummy certificate.
-
-
-## Complication 3: Server Name Indication
-
-One of the big limitations of vanilla SSL is that each certificate requires its
-own IP address. This means that you couldn't do virtual hosting where multiple
-domains with independent certificates share the same IP address. In a world
-with a rapidly shrinking IPv4 address pool this is a problem, and we have a
-solution in the form of the [Server Name
-Indication](http://en.wikipedia.org/wiki/Server_Name_Indication) extension to
-the SSL and TLS protocols. This lets the client specify the remote server name
-at the start of the SSL handshake, which then lets the server select the right
-certificate to complete the process.
-
-SNI breaks our upstream certificate sniffing process, because when we connect
-without using SNI, we get served a default certificate that may have nothing to
-do with the certificate expected by the client. The solution is another tricky
-complication to the client connection process. After the client connects, we
-allow the SSL handshake to continue until just _after_ the SNI value has been
-passed to us. Now we can pause the conversation, and initiate an upstream
-connection using the correct SNI value, which then serves us the correct
-upstream certificate, from which we can extract the expected CN and SANs.
-
-There's another wrinkle here. Due to a limitation of the SSL library mitmproxy
-uses, we can't detect that a connection _hasn't_ sent an SNI request until it's
-too late for upstream certificate sniffing. In practice, we therefore make a
-vanilla SSL connection upstream to sniff non-SNI certificates, and then discard
-the connection if the client sends an SNI notification. If you're watching your
-traffic with a packet sniffer, you'll see two connections to the server when an
-SNI request is made, the first of which is immediately closed after the SSL
-handshake. Luckily, this is almost never an issue in practice.
-
-## Putting it all together
-
-Lets put all of this together into the complete explicitly proxied HTTPS flow.
-
-<img src="explicit_https.png"/>
-
-<table class="table">
- <tbody>
- <tr>
- <td><b>1</b></td>
- <td>The client makes a connection to mitmproxy, and issues an HTTP
- CONNECT request.</td>
- </tr>
- <tr>
- <td><b>2</b></td>
-
- <td>Mitmproxy responds with a 200 Connection Established, as if it
- has set up the CONNECT pipe.</td>
- </tr>
- <tr>
- <td><b>3</b></td>
-
- <td>The client believes it's talking to the remote server, and
- initiates the SSL connection. It uses SNI to indicate the hostname
- it is connecting to.</td>
- </tr>
-
- <tr>
- <td><b>4</b></td>
-
- <td>Mitmproxy connects to the server, and establishes an SSL
- connection using the SNI hostname indicated by the client.</td>
-
- </tr>
- <tr>
- <td><b>5</b></td>
-
- <td>The server responds with the matching SSL certificate, which
- contains the CN and SAN values needed to generate the interception
- certificate.</td>
- </tr>
- <tr>
- <td><b>6</b></td>
-
- <td>Mitmproxy generates the interception cert, and continues the
- client SSL handshake paused in step 3.</td>
- </tr>
- <tr>
- <td><b>7</b></td>
-
- <td>The client sends the request over the established SSL
- connection.</td>
- </tr>
- <tr>
- <td><b>7</b></td>
-
- <td>Mitmproxy passes the request on to the server over the SSL
- connection initiated in step 4.</td>
- </tr>
- </tbody>
-</table>
-
-
-<div class="page-header">
- <h1>Transparent HTTP</h1>
-</div>
-
-When a transparent proxy is used, the HTTP/S connection is redirected into a
-proxy at the network layer, without any client configuration being required.
-This makes transparent proxying ideal for those situations where you can't
-change client behaviour - proxy-oblivious Android applications being a common
-example.
-
-To achieve this, we need to introduce two extra components. The first is a
-redirection mechanism that transparently reroutes a TCP connection destined for
-a server on the Internet to a listening proxy server. This usually takes the
-form of a firewall on the same host as the proxy server -
-[iptables](http://www.netfilter.org/) on Linux or
-[pf](http://en.wikipedia.org/wiki/PF_\(firewall\)) on OSX. Once the client has
-initiated the connection, it makes a vanilla HTTP request, which might look
-something like this:
-
-<pre>GET /index.html HTTP/1.1</pre>
-
-Note that this request differs from the explicit proxy variation, in that it
-omits the scheme and hostname. How, then, do we know which upstream host to
-forward the request to? The routing mechanism that has performed the
-redirection keeps track of the original destination for us. Each routing
-mechanism has a different way of exposing this data, so this introduces the
-second component required for working transparent proxying: a host module that
-knows how to retrieve the original destination address from the router. In
-mitmproxy, this takes the form of a built-in set of
-[modules](https://github.com/mitmproxy/mitmproxy/tree/master/libmproxy/platform)
-that know how to talk to each platform's redirection mechanism. Once we have
-this information, the process is fairly straight-forward.
-
-<img src="transparent.png"/>
-
-
-<table class="table">
- <tbody>
- <tr>
- <td><b>1</b></td>
- <td>The client makes a connection to the server.</td>
- </tr>
- <tr>
- <td><b>2</b></td>
-
- <td>The router redirects the connection to mitmproxy, which is
- typically listening on a local port of the same host. Mitmproxy
- then consults the routing mechanism to establish what the original
- destination was.</td>
- </tr>
- <tr>
- <td><b>3</b></td>
-
- <td>Now, we simply read the client's request...</td>
- </tr>
-
- <tr>
- <td><b>4</b></td>
-
- <td>... and forward it upstream.</td>
-
- </tr>
- </tbody>
-</table>
-
-<div class="page-header">
- <h1>Transparent HTTPS</h1>
-</div>
-
-The first step is to determine whether we should treat an incoming connection
-as HTTPS. The mechanism for doing this is simple - we use the routing mechanism
-to find out what the original destination port is. By default, we treat all
-traffic destined for ports 443 and 8443 as SSL.
-
-From here, the process is a merger of the methods we've described for
-transparently proxying HTTP, and explicitly proxying HTTPS. We use the routing
-mechanism to establish the upstream server address, and then proceed as for
-explicit HTTPS connections to establish the CN and SANs, and cope with SNI.
-
-<img src="transparent_https.png"/>
-
-
-<table class="table">
- <tbody>
- <tr>
- <td><b>1</b></td>
- <td>The client makes a connection to the server.</td>
- </tr>
- <tr>
- <td><b>2</b></td>
-
- <td>The router redirects the connection to mitmproxy, which is
- typically listening on a local port of the same host. Mitmproxy
- then consults the routing mechanism to establish what the original
- destination was.</td>
- </tr>
- <tr>
- <td><b>3</b></td>
-
- <td>The client believes it's talking to the remote server, and
- initiates the SSL connection. It uses SNI to indicate the hostname
- it is connecting to.</td>
- </tr>
-
- <tr>
- <td><b>4</b></td>
-
- <td>Mitmproxy connects to the server, and establishes an SSL
- connection using the SNI hostname indicated by the client.</td>
-
- </tr>
- <tr>
- <td><b>5</b></td>
-
- <td>The server responds with the matching SSL certificate, which
- contains the CN and SAN values needed to generate the interception
- certificate.</td>
- </tr>
- <tr>
- <td><b>6</b></td>
-
- <td>Mitmproxy generates the interception cert, and continues the
- client SSL handshake paused in step 3.</td>
- </tr>
- <tr>
- <td><b>7</b></td>
-
- <td>The client sends the request over the established SSL
- connection.</td>
- </tr>
- <tr>
- <td><b>7</b></td>
-
- <td>Mitmproxy passes the request on to the server over the SSL
- connection initiated in step 4.</td>
- </tr>
- </tbody>
-</table>
-
-
-[^ssl]: I use "SSL" to refer to both SSL and TLS in the generic sense, unless otherwise specified.