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  1. Web Security Academy
  2. Request smuggling
  3. Advanced

Advanced request smuggling

In this section, we'll build on the concepts you've learned so far and teach you some more advanced HTTP request smuggling techniques. We'll also cover a variety of HTTP/2-based attacks that are made possible thanks to Burp's unique HTTP/2-testing capabilities. Don't worry if you're new to HTTP/2 - we'll cover all the essentials as we go.

In particular, we'll look at:

To help you practice what you've learned, we've provided deliberately vulnerable labs throughout. These are based on real-world vulnerabilities first presented at Black Hat USA 2021 by our Director of Research, James Kettle.

HTTP/2 request smuggling

In this section, we'll show you how, contrary to popular belief, implementing HTTP/2 has actually made many websites more vulnerable to request smuggling, even if they were previously safe from these kinds of attacks.

HTTP/2 message length

Request smuggling is fundamentally about exploiting discrepancies between how different servers interpret the length of a request. HTTP/2 introduces a single, robust mechanism for doing this, which has long been thought to make it inherently immune to request smuggling.

Although you won't see this in Burp, HTTP/2 messages are sent over the wire as a series of separate "frames". Each frame is preceded by an explicit length field, which tells the server exactly how many bytes to read in. Therefore, the length of the request is simply the sum of its frame lengths.

In theory, this mechanism means there is no opportunity for an attacker to introduce the ambiguity required for request smuggling, as long as the website uses HTTP/2 end to end. In the wild, however, this is often not the case due to the widespread but dangerous practice of HTTP/2 downgrading.

HTTP/2 downgrading

HTTP/2 downgrading is the process of rewriting HTTP/2 requests using HTTP/1 syntax to generate an equivalent HTTP/1 request. Web servers and reverse proxies often do this in order to offer HTTP/2 support to clients while communicating with back-end servers that only speak HTTP/1. This practice is a prerequisite for many of the attacks covered in this section.

HTTP/2 downgrading

Note on HTTP/2 message representation

As HTTP/2 is a binary protocol, we've used some artistic license to represent HTTP/2 messages in a human-readable format throughout these materials:

  • We display each message as a single entity, rather than separate "frames".

  • We display the headers using plain text name and value fields.

  • We prefix pseudo-header names with a colon to help differentiate them from normal headers.

This closely resembles the way Burp represents HTTP/2 messages in the Inspector, but note that they don't actually look like this on the wire.

H2.CL vulnerabilities

HTTP/2 requests don't have to specify their length explicitly in a header. During downgrading, this means front-end servers often add an HTTP/1 Content-Length header, deriving its value using HTTP/2's built-in length mechanism. Interestingly, HTTP/2 requests can also include their own content-length header. In this case, some front-end servers will simply reuse this value in the resulting HTTP/1 request.

The spec dictates that any content-length header in an HTTP/2 request must match the length calculated using the built-in mechanism, but this isn't always validated properly before downgrading. As a result, it may be possible to smuggle requests by injecting a misleading content-length header. Although the front-end will use the implicit HTTP/2 length to determine where the request ends, the HTTP/1 back-end has to refer to the Content-Length header derived from your injected one, resulting in a desync.

Front-end (HTTP/2)

:method POST
:path /example
:authority vulnerable-website.com
content-type application/x-www-form-urlencoded
content-length 0

GET /admin HTTP/1.1 Host: vulnerable-website.com Content-Length: 10 x=1

Back-end (HTTP/1)

POST /example HTTP/1.1
Host: vulnerable-website.com
Content-Type: application/x-www-form-urlencoded
Content-Length: 0

GET /admin HTTP/1.1
Host: vulnerable-website.com
Content-Length: 10

x=1
GET / H

Tip

When performing some request smuggling attacks, you will want headers from the victim's request to be appended to your smuggled prefix. However, these can interfere with your attack in some cases, resulting in duplicate header errors and suchlike. In the example above, we've mitigated this by included a trailing parameter and a Content-Length header in the smuggled prefix. By using a Content-Length header that is slightly longer than the body, the victim's request will still be appended to your smuggled prefix but will be truncated before the headers.

H2.TE vulnerabilities

Chunked transfer encoding is incompatible with HTTP/2 and the spec recommends that any transfer-encoding: chunked header you try to inject should be stripped or the request blocked entirely. If the front-end server fails to do this, and subsequently downgrades the request for an HTTP/1 back-end that does support chunked encoding, this can also enable request smuggling attacks.

Front-end (HTTP/2)

:method POST
:path /example
:authority vulnerable-website.com
content-type application/x-www-form-urlencoded
transfer-encoding chunked

0 GET /admin HTTP/1.1 Host: vulnerable-website.com Foo: bar

Back-end (HTTP/1)

POST /example HTTP/1.1
Host: vulnerable-website.com
Content-Type: application/x-www-form-urlencoded
Transfer-Encoding: chunked

0

GET /admin HTTP/1.1
Host: vulnerable-website.com
Foo: bar

If a website is vulnerable to either H2.CL or H2.TE request smuggling, you can potentially leverage this behavior to perform the same attacks that we covered in our previous request smuggling labs.

Response queue poisoning

Response queue poisoning is a powerful request smuggling attack that enables you to steal arbitrary responses intended for other users, potentially compromising their accounts and even the entire site.

Request smuggling via CRLF injection

Even if websites take steps to prevent basic H2.CL or H2.TE attacks, such as validating the content-length or stripping any transfer-encoding headers, HTTP/2's binary format enables some novel ways to bypass these kinds of front-end measures.

In HTTP/1, you can sometimes exploit discrepancies between how servers handle standalone newline (\n) characters to smuggle prohibited headers. If the back-end treats this as a delimiter, but the front-end server does not, some front-end servers will fail to detect the second header at all.

Foo: bar\nTransfer-Encoding: chunked

This discrepancy doesn't exist with the handling of a full CRLF (\r\n) sequence because all HTTP/1 servers agree that this terminates the header.

On the other hand, as HTTP/2 messages are binary rather than text-based, the boundaries of each header are based on explicit, predetermined offsets rather than delimiter characters. This means that \r\n no longer has any special significance within a header value and, therefore, can be included inside the value itself without causing the header to be split:

foo bar\r\nTransfer-Encoding: chunked

This may seem relatively harmless on its own, but when this is rewritten as an HTTP/1 request, the \r\n will once again be interpreted as a header delimiter. As a result, an HTTP/1 back-end server would see two distinct headers:

Foo: bar
Transfer-Encoding: chunked

HTTP/2 request splitting

When we looked at response queue poisoning, you learned how to split a single HTTP request into exactly two complete requests on the back-end. In the example we looked at, the split occurred inside the message body, but when HTTP/2 downgrading is in play, you can also cause this split to occur in the headers instead.

This approach is more versatile because you aren't dependent on using request methods that are allowed to contain a body. For example, you can even use a GET request:

:method GET
:path /
:authority vulnerable-website.com
foo

bar\r\n \r\n GET /admin HTTP/1.1\r\n Host: vulnerable-website.com

This is also useful in cases where the content-length is validated and the back-end doesn't support chunked encoding.

Accounting for front-end rewriting

To split a request in the headers, you need to understand how the request is rewritten by the front-end server and account for this when adding any HTTP/1 headers manually. Otherwise, one of the requests may be missing mandatory headers.

For example, you need to ensure that both requests received by the back-end contain a Host header. Front-end servers typically strip the :authority pseudo-header and replace it with a new HTTP/1 Host header during downgrading. There are different approaches for doing this, which can influence where you need to position the Host header that you're injecting.

Consider the following request:

:method GET
:path /
:authority vulnerable-website.com
foo

bar\r\n \r\n GET /admin HTTP/1.1\r\n Host: vulnerable-website.com

During rewriting, some front-end servers append the new Host header to the end of the current list of headers. As far as an HTTP/2 front-end is concerned, this after the foo header. Note that this is also after the point at which the request will be split on the back-end. This means that the first request would have no Host header at all, while the smuggled request would have two. In this case, you need to position your injected Host header so that it ends up in the first request once the split occurs:

:method GET
:path /
:authority vulnerable-website.com
foo

bar\r\n Host: vulnerable-website.com\r\n \r\n GET /admin HTTP/1.1

You will also need to adjust the positioning of any internal headers that you want to inject in a similar manner.

Tip

In the example above, we've split the request in a way that triggers response queue poisoning, but you can also smuggle prefixes for classic request smuggling attacks in this way. In this case, your injected headers may clash with the headers in the request that is appended to your prefix on the back-end, resulting in duplicate header errors or causing the request to be terminated in the wrong place. To mitigate this, you can include a trailing body parameter in the smuggled prefix along with a Content-Length header that is slightly longer than the body. The victim's request will still be appended to your smuggled prefix but will be truncated before the headers.

HTTP request tunnelling

Many of the request smuggling attacks we've covered so far are only possible because the same connection between the front-end and back-end server is used for handling multiple requests. HTTP request tunnelling provides a way to craft high-severity exploits even when there is no connection reuse at all.

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