September 29, 2013

Nobody Cares About Signed Gems

This postmortem originally appeared on the site that contained a proof-of-concept system to crytographically sign ruby software packages so they could be authenticated on download. The system was developed after, the primary distribution network was hacked and compromised gems were uploaded.

This was by far the most toxic experience I’ve ever had trying to write Open Source software, but here I just tried to focus on how uninterested developers are in software authentication, and how quickly a funnel of tens of thousands of programmers visiting the site resulted in only a half dozen or so actual test drives of the software.

Nobody Cares About Signed Gems

The signing key for the CA expired on August 17, 2013. As an experiment, I decided to leave the key in an expired state and see if and when anyone would notice or complain. Today (Sept 29, 2013) someone finally asked about it on the mailing list. Just over 45 days.

Why would I let the key expire?

I originally wrote rubygems-openpgp a few years ago because I wasn’t happy with the existing signing solution and was looking for a side project to work on. No one paid attention. It was clear that I was the sole user. So the project sat there in maintenance mode.

Then… A few years later… got hacked! There was no way to tell if the gems on the site had been compromised. Suddenly there was interest in signing gems. A few people found my project and submitted pull requests. Now that there were a few users, I dived back in and decided to take the gem from the proof-of-concept stage to a stable piece of software. I spent the next month doing so.

Along the way one-too-many people said that OpenPGP wasn’t useful because most end users couldn’t get into the strong set in the Web-of-Trust, ignoring the fact that distributions systems such as apt silently use OpenPGP behind the scenes. So I created this site as a proof-of-concept CA. The implementation was simple. I didn’t even really need a rails website. The content is exclusively jekyll. Basically a user would sign up. I would manually verify that they had control of their email, signing key, and had published gems on I would then manually sign off on their key with a smart-card set aside for that purpose. I got a MVP up and running, and started circulating the link.

This brought tens of thousands of users to the site. Plenty of upvotes on reddit. Success, right?


One metric to measure success would be the number of people who requested certification. That number was less than a dozen.

But we need to keep in mind these are just gem authors, right? Those should be orders of magnitude rarer than the actual users, right?


I provide a test gem called openpgp-signed-hola. It is the standard “Hello World” gem with the addition of a digital signature. All the documentation referred users to use this gem to see how things work. has nice charts that show how many times a version of gem has been downloaded. Of course this number includes bots and other automated retrievals in addition to actual human users testing out rubygems-openpgp. But it does provide an upper bound of the maximum amount of people who tried to verify the test gem.

No more than two dozen people tried to manually verify the test gem. To be honest, I think this number is probably high. I think the number was much lower.

Honestly, I found this disappointing. It takes less than 5 minutes to test gem verification. You would think that number would be at least equal to the number of upvotes on reddit. That people would actually read the site and try things out, instead of hitting the upvote button and going away. You would think the people writing blog posts about how important signing was would take 5 minutes to try out the software. But alas, they didn’t.

But it takes time for software adoption, right?

I had a few interested users. There were finally signed gems on signed by people other than me. I expected that would be enough that I’d get a trickle of signups over the course of the next year. But after the initial burst of interest activity came to a halt. After several months without receiving a single sign-up on the site, inquiries on the mailing lists, or issues in github, I found myself wondering why I was paying $20 a month to heroku to for https hosting. I went ahead and canceled that. And that’s when I decided to let the signing key expire.

Why would I let the key expire again?

The key was setup to expire every 30 days. This was basically a way to enforce a revocation policy. If the key itself was compromised (unlikely, it’s on a smart card), or if I was forced to issue revocations on the CA’s behalf, a periodic expiration would force users to retrieve updated certificates and hence any revocations.

If there was a small community of people who were using the CA keys, I would quickly get an email they started noticing that all their software was expired. It would at least provide some indication that I should continue to maintain the CA.

45 days later someone finally noticed.

That doesn’t prove nobody cares about signed gems, it just proves nobody cares about rubygems-openpgp


But I haven’t seen any activity on the X.509 front either. After the rubygems compromise, things were supposed to change. That was finally the kick-in-the-pants the community needed to fix things and take gem authentication seriously.

  • The rubygems-trust project was started to setup replacement rubygems with CA capabilities. Activity fizzled out after a month with no visible results.

  • A few people tried to start signing their gems with X509, but most gave up because it was impractical.

  • The X509 code in rubygems itself has essentially the same TODO list as it did when the code was initially merged in 2007.

The above points, as the rest of this essay, is NOT an attempt to call anyone out, it’s simply what I’ve observed. Getting X509 signing and verification of gems to actually be used isn’t any farther along than it was before the hack either.

In Conclusion

I’m primarily documenting my experiences with the project so they’re available if/when there is push to start signing gems in the future.

This post is negative, but I hope it doesn’t come across as bitter. I don’t regret any of the time I spent on rubygems-openpgp or the CA. It was fun! And I’ll continue to maintain rubygems-openpgp if it’s needed. (The CA, on the other hand, will probably go away when the domain expires and/or I want to use my free heroku hours for another project.)

I do wish people were more interested in signing their gems one way or another, but then again I wish more people (especially techies) would encrypt their damn emails! Instead they’ll write blog posts and tweet about the importance of doing so, but won’t actually change their habits.