Over a million developers have joined DZone.

The Bare Minimum a Developer Should Know About Transport Level Security

DZone's Guide to

The Bare Minimum a Developer Should Know About Transport Level Security

Transport Level Security, or TLS, is a building block of many facets of cybersecurity. Read on to see what you, as a dev, need to know about it.

· Security Zone
Free Resource

Discover how to provide active runtime protection for your web applications from known and unknown vulnerabilities including Remote Code Execution Attacks.

Transport level security, also known as TLS or SSL, is a way to secure a connection from prying eyes. This is done using math, so we know that this is good. I can also count to 20 if I take my shoes off, so you know you can trust me on that.

On a slightly more serious note, SSL/TLS gives us one-half of the security requirements we need. We can negotiate a secure cipher and a key and rest assured that no outside source can listen to what we are saying to the other side.

Notice that I said one half? The other half is knowing who is on the other side. This is usually done using certificates, which provide the public/private keys for the connection, and the signer of the certificate is what provides the identity of the remote connection. In other words, when I'm using SSL/TLS, I need to also know who am I going to be talking to and then verify in some manner using the certificate that they provide me that they are indeed who they say they are.

Let us deconstruct the simplest of operations, GET https://my-awesome-service:

  • First, we need to find the IP of my-awesome-service.
  • Then, we negotiate a secured connection with this IP.
  • Profit?

This would seem like the end of things, but we need to dig a bit deeper. I'm contacting my-awesome-service, but before I can do that, I need to first check what IP maps to that name. To do that, I need to do a DNS query. DNS is usually unsecured, so anyone can see what kind of hostnames you are asking for. What is more interesting, there is absolutely nothing that prevents a bad guy from spoofing DNS responses to you. In fact, this has been a very fruitful area of attacks.

There is DNS Sec, which will protect you from forged requests in the last mile, but less than 15% of the worldwide record is actually signed using DNS Sec, so you can usually assume that you won't be using that. In fact, even if the domain is signed, because so many domains aren't, most systems will be configured to assume that an unsigned request is valid by default, instead of the other way around. This makes things fun at security circles, I'm sure. But for our purposes, you should know that DNS is great, but you probably shouldn't rely on it. Errors, mistakes, and outright forgery is possible.

If you want to see a simple example, head over to "/etc/hosts" on Linux or "%windir%/system32/drivers/etc/hosts" on Windows and add some fake entries there. You can have fun with pointing stackoverflow.com to lmgtfy.com, for example.

You can do it like so: stackoverflow.com

With being the IP address of lmgtfy.com. Once you have done that, requests that you think are going to stackoverflow.com will be sent to lmgtfy.com, with hilarity soon to follow.

Oh, except that this won't work. StackOverflow is using HTTPS, and they are also using HSTS (HTTP Strict Transport Security). Basically, this means that once you have visited StackOverflow even once, your browser will remember that this domain requires HTTPS to work, and will outright refuse to access the site without it.

But what is the problem? HSTS is great, but it just requires HTTPS. So if I managed to spoof your DNS somehow (if I could modify the host's file, I'm already admin and own the box, but assuming that I haven't gotten there), all I would really need to do is to make sure that the websites I spoof give you a certificate. But here the second half of SSL comes into play. The client making the request is going to validate that the hostname it provides is located in the certificate that the server provided. So far, that makes sense. But the server could just generate whatever certificate it wants, no?

In order to prevent that, there is a chain of trust. Basically, you need to have a list of trusted root certificates that your trust, and you verify that the certificate that you got from the remote server was directly (or indirectly, in some cases) signed by them, presumably after some level of verification. Reading the actual list of trusted roots is interesting.

The Mozilla list has about 160 root certificates and includes such entities as the Government of Turkey, where all journalists will tell you that the government is free and fair (all those who would say otherwise are not there). On my Windows machine, there are about 50 root certificates, and at least at one point that included Equifax, who we know can be trusted. On a work machine, you can be fairly certain that there are additional root certificates (from the domain, for example). But for now, we'll ignore the possibility of a bad trusted root certificate and assume that the system is working as it is meant to be. And to be fair, any violations are punished by revocation of the root certificate. This is the current state of the Equifax root certificate on my machine, for example, it has been revoked.

Another mitigation here is that there is an ongoing process to encourage certificate issuance transparency. That means that a domain can specify which CA is allowed to issue certificates for it (called key pinning). Of course, this is distributed via DNS, and we have already seen that this ain't too hot either, but it is a matter of defense in depth. Key pinning also creates some fun ransomware options. If I can get control over your DNS records in some manner, including by spoofing them, I can set key pinning to a key that only I have, resulting in a large number of users unable to access your site because it is not using the "correct" key. But I'm digressing. There is also the notion that a browser can do something called OCSP (online certificate status protocol), which basically states that a user can query the CA for whatever certificate is valid. The catch is that if the CA doesn't answer (vs. answer that the cert is invalid), the certificate is assumed to be valid. This is done because a CA going down may then take down significant parts of the internet, leaving aside such concerns as the latency issues that this would require.

If you think the notion of a rouge trusted root is fantasy, there have been multiple cases of false certificates (DigiNotar, Symantec, TrustWave, etc), each with hundreds of certificates being issues (or even blank checks certificates, which can be used to generate any certificate you wish for). To combat that, there is now an effort to implement Certificate Transparency. Basically, in order to trust a certificate, it must show up in a public list. That allows admins to check that no one issued certificates for their domains.

This post has gotten quite long, so I'll leave you with this worrisome ending and continue talking about how this applies to distributed systems in the next post.

Find out how Waratek’s award-winning application security platform can improve the security of your new and legacy applications and platforms with no false positives, code changes or slowing your application.

security ,ssl/tls ,server security ,database security

Published at DZone with permission of Oren Eini, DZone MVB. See the original article here.

Opinions expressed by DZone contributors are their own.

{{ parent.title || parent.header.title}}

{{ parent.tldr }}

{{ parent.urlSource.name }}