Dropbox has become a daily part of my life. I rely on it to synchronise data between my growing set of devices. But how much of an impact does it have on the security of my system? I decided to find out by digging around in exactly what it does to my machine, or more specifically, the processes running on it.

The first thing I want to check out is what modules are loaded into various processes. Tools like Dropbox like to extend the functionality of other programs using shell extensions, which are nothing more than specially designed DLLs loaded into process memory. Let’s see what we’ve got…

Interesting! Looks like we’ve got two extension DLLs, one 32-bit and one 64-bit. These are likely used to add extra context menu options when right-clicking on files. Now let’s find out where they get injected. For this, we’ll use good ol’ trusty Process Explorer. By going to Find » Find Handle or DLL, we can search for the DLLs in running processes.

It looks like it’s being loaded into processes that have windows created, which implies it’s probably an AppInit DLL, but it turns out not to be the case – the registry key doesn’t contain that DLL. This implies that there’s something more active going on, and that Dropbox actively selects which processes to inject into. I may be mistaken here, I’m not sure. Either way, though, it’s a little odd that it chose to inject into Notepad++ and other innocuous processes.

(Update: thanks to zeha and 312c on Reddit for pointing out that it’s likely injected via the standard file browser shell, due to the Dropbox icon in the favourites list)

The biggest problem becomes clear when you take a look at the module in a running process. In this case, it’s Firefox:

Notice that the Dropbox extension DLL doesn’t have the ASLR flag set. This means that any vulnerability in Firefox becomes a lot easier to exploit, since the Dropbox module provides an unrandomised anchor for a ROP chain. Ignore PowerHookMenu.dll here – I’m aware of that issue and have notified the developer, but it’s infrequently seen on people’s machines so it’s not so bad.

Let’s just quickly verify that the DLL isn’t ASLR enabled at all, by checking the DLL characteristics flags in the file…

Definitely not enabled.

Anyway, the take-away issue here is that Dropbox arbitrarily injects an ASLR-disabled DLL into various 32-bit and 64-bit processes, causing significant degradation in the efficacy of ASLR across the entire system. With no ASLR, an attacker could craft an exploit payload that utilises executable code within the injected DLL to product a ROP chain, leading to code execution. This is significantly problematic in high-risk programs like web browsers and torrent clients.

I notified Dropbox of this back when version 1.0.0.17 was the latest version, but got not response. I’ve since tried again, but had no luck. I’m hoping that going public will give them the kick they need to get it fixed. In the meantime, a good mitigation is to install EMET and set a policy to enforce Mandatory ASLR. All of this was re-tested against Dropbox 2.0.22, with versions 1.0.0.19 of both the 32-bit and 64-bit DLLs. The operating system used was Windows 7 x64 SP1.

Update: Brad “spender” Spengler (of grsec fame) has noted that the latest version of Dropbox has ASLR enabled for the 64-bit DLL, but still doesn’t on 32-bit.

Update 2: Dropbox responds: “Our engineers are aware of this issue and actively working on fixing it. Unfortunately, I can’t give you an exact timeline that a fix will become available. If you have any additional questions or concerns please let me know.”

Update 3: @_sinn3r has done some awesome work on the exploitability of these issues, over at Metasploit. Definitely worth a read.