Searching for Weak Debian / Ubuntu SSL Certificates

Tuxkeys_2 I’ve seen a number of people promote packages that have shipped for Debian and Ubuntu, which allow users to scan their collected keys – OpenSSH or OpenSSL or OpenVPN, to discover whether they’re too weak to be of any functional use. [See my earlier story on Debian and the OpenSSL PRNG]

These tools all have one problem.

They run on the Linux systems in question, and they scan the certificates in place.

Given that the keys in question could be as old as 2 years, it seems likely that many of them have migrated off the Linux platforms on which they have started, and onto web sites outside of the Linux platform.

Or, there may simply be a requirement for a Windows-centric security team to be able to scan existing sites for those Linux systems that have been running for a couple of years without receiving maintenance (don’t nod like that’s a good thing).

So, I’ve updated my SSLScan program. I’m attaching a copy of the tool to this blog post, (along with a copy of the Ubuntu OpenSSL blacklists for 1024-bit and 2048-bit keys if I can get approval), though of course I would suggest keeping up with your own copies of these blacklists. It took a little research to find out how to calculate the quantity being used for the fingerprint by Debian, but I figure that it’s best to go with the most authoritative source to begin with.

Please let me know if there are other, non-authoritative blacklists that you’d like to see the code work with – for now, the tool will simply search for “blacklist.RSA-1024” and “blacklist.RSA-2048” in the current directory to build a list of weak key fingerprints.

I’ve found a number of surprising certificates that haven’t been reissued yet, and I’ll let you know about them after the site owners have been informed.

[Sadly, I didn’t find before it was changed – its certificate is shared with, of all places, – yes, the White House, home of the President of America, is hosted from the same server as the Chinese government. The certificate was changed yesterday, 2008/5/21.’s certificate was issued two days ago, 2008/5/20 – coincidence?]

My examples are from the web, but the tool will work on any TCP service that responds immediately with an attempt to set up an SSL connection – so LDAP over SSL will work, but FTP over SSL will not. It won’t work with SSH, because that apparently uses a different key format.

Simply run SSLScan, and enter the name of a web site you’d like to test, such as– don’t enter “http://” at the beginning, but remember that you can test a host at a non-standard port (which you will need to do for LDAP over SSL!) by including the port in the usual manner, such as

If you’re scanning a larger number of sites, simply put the list of addresses into a fie, and supply the file’s name as the argument to SSLScan.

Let me know if you think of any useful additions to the tool.

Here is some slightly modified output from a sample run of the tool (the names have been changed to protect the innocent):Image-0195_2

The text to look for here is “>>>This Key Is A Weak Debian Key<<<“.

One thought on “Searching for Weak Debian / Ubuntu SSL Certificates”

  1. This is a WINDOWS or DOS app?  Makes it somewhat useless…

    Far from useless – did you read the post? Where I mentioned that this could be used if you are one of a Windows-centric security team that needs to verify that your web sites etc are not plagued by weak keys? The tools posted on the Ubuntu / Debian side so far only probe local keys, whereas this probes remote keys (via SSL) – yes, there should be a Linux tool that does this, but that’s not to say that a Windows tool is useless – why, with this tool, I’ve found four web sites already whose owners will be receiving a polite email from me suggesting that they install the fix. One of them, rather ironically, had a “front-page news story” on just this problem.

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