Author Archive: gsandhu

Lessons Learned from Improving Transport Layer Security (TLS) at Adobe

Transport Layer Security (TLS) is the foundation of security on the internet. As our team evolved from primarily consultative role to solve problems for the entire company, we chose TLS as one of the areas to improve. The goal of this blog post is to share the lessons we’ve learned from this project.

TLS primer

TLS is a commonly used protocol to secure communications between two entities. If a client is talking to a server over TLS, it expects the following:

  1. Confidentiality – The data between the client and the server is encrypted and a network eavesdropper should not be able to decipher the communication.
  2. Integrity – The data between the client and the server should not be modifiable by a network attacker.
  3. Authentication – In the most common case, the identity of the server is authenticated by the client during the establishment of the connection via certificates. You can also have 2-way authentication, but that is not commonly used.

Lessons learned

Here are the main lessons we learned:

Have a clearly defined scope

Instead of trying to boil the ocean, we decided to focus on around 100 domains belonging to our Creative Cloud, Document Cloud and Experience Cloud solutions. This helped us focus on these services first versus being drowned by the thousands of other Adobe domains.

Have clearly defined goals

TLS is a complicated protocol and the definition of a “good” TLS configuration keeps changing over time. We wanted a simple, easy to test, pass/fail criteria for all requirements on the endpoints in scope. We ended up choosing the following:

SSL Labs grade

SSL Labs does a great job of testing a TLS configuration and boiling it down to a grade. Grade ‘A’ was viewed as a pass and anything else was considered a fail. There might be some endpoints that had valid reasons to support certain ciphers that resulted in a lower grade. I will talk about that later in this post.

Apple Transport Security

Apple has a minimum bar for TLS configuration that all endpoints must pass if iOS apps are to connect to that endpoint. We reviewed this criteria and all the requirements were deemed sensible. We decided to make it a requirement for all endpoints, regardless if an endpoint was being accessed from an iOS app or not. We found a few corner cases where a configuration would get SSL Labs grade A and fail ATS (and vice-versa) that we resolved on a case-by-case basis.

HTTP Strict Transport Security

HSTS (HTTP Strict Transport Security) is a HTTP response header that informs compliant clients to always use HTTPS to connect to a website. It helps solve the problem of initial request being made over plain HTTP when a user types in the site without specifying the protocol and helps prevent the hijacking of connections. When a compliant client receives this header, it only uses HTTPS to make connections to this website for a max-age value set by the header. The max-age count is reset every time the client receives this header. You can read the details about HSTS in RFC 6797.

Complete automation of testing workflow

We wanted to have minimal human cost for these tests on an ongoing basis. This project allowed us to utilize our Security Automation Framework. Once the scans are setup and scheduled, they keep running daily and the results are passed on to us via email/slack/etc. After the initial push to get all the endpoints pass all the tests, it was very easy to catch any drift when we saw a failed test. Here is what these results looks like in the SAF UI:

Devil is in the Detail

From a high level it seems fairly straightforward to go about improving TLS configurations. However, it is a little more complicated when you get into the details. I wanted to talk a little bit about how we went about removing ciphers that were hampering the SSL Labs grade.

To understand the issues, you have to know a little bit about the TLS handshake. During the handshake, the client and the server decide on which cipher to use for the connection. The client sends the list of ciphers it supports in the client “hello” message of the handshake to the server. If server side preference is enabled, the cipher that is listed highest in the server preference and also supported by client is picked. In our case, the cipher that was causing the grade degradation was listed fairly high on the list. As a result, when we looked at the ciphers used for connections, this cipher was used in a significant percentage of the traffic. We didn’t want to just remove it because of the potential risk of dropping support for some customers without any notification. Therefore, we initially moved it to the bottom of the supported cipher list. This reduced the percentage of traffic using that cipher to a very small value. We were then able to identify that a partner integration was responsible to all the traffic for this cipher. We reached out to that partner and notified them to make appropriate changes before disabling that cipher. If you found this interesting, you might want to consider working for us on these projects.

Future work

In the future, we want to expand the scope of this project. We also want to expand the requirements for services that have achieved the requirements described in this post. One of the near-term goals is to get some of our domains added to the HSTS preload list. Another goal is to do more thorough monitoring of certificate transparency logs for better alerting for new certificates issued for Adobe domains. We have also been experimenting with HPKP. However, as with all new technologies, there are issues we must tackle to continue to ensure the best balance of security and experience for our customers.

Gurpartap Sandhu
Security Researcher