This is Day 10 of Butter Days, from Ada’s Technical Books and Cafe in Seattle, WA.

Last week I updated the proxy to work with https so that requests coming from my laptop are actually secure.

However, because I don’t have certificates set up, clients have to ignore certificate errors to work with the proxy. Originally I was thinking I could ignore this and keep going, but I think I’m going to bite the bullet and deal with it now. I’ll have to do it eventually, and it’ll hopefully save me some work in trying to figure out how to get all the client libraries to ignore certificate errors.

See Day 1 of Butter Days for context on what I’m ultimately trying to build.

UPDATE: This post is mostly about all the walls I ran into, but in Butter Days 10.5 I was actually able to get something working based on what I learned here.

Trusting A Certificate

Before I look into controlling what certificates the proxy presents to the client, I want to make sure I know how get all my client applications to trust whatever I’m sending them.

This response claims that trusting a certificate can’t easily be done system wide and that each application may be configured in its own way. For example, curl has a --cacert option for this. Maybe configuring this in the most common SSL libraries (like OpenSSL and GnuTLS) will save me from having to figure this out all over again with every single language and tool.

Unfortunately, this page for GnuTLS and this response about OpenSSL make it clear that these libraries expect the user to configure trust settings rather than being opinionated about trusted cert paths. That makes sense, but it means that I’ll have to configure this elsewhere, probably in more platform and language specific ways.

I can see that golang, python (ironically the link to the docs in that post failed with an SSL error for me), and rust all have ways of trusting custom CAs, so I unfortunately have lots of options.

One thing looks promising though. In the rust version they use update-ca-certificates. That seems like it might be the most standard way to do it, at least for Linux.

I think this is probably actually the way. I searched for “update-ca-certificates mac” to see if it’s cross platform and found this gist which shows how to trust certs system wide for a number of different platforms. Thanks random internet user! That’s at least a start, and I can dig into the docs for each of those commands when I really want to get serious about it.

Generating A Certificate

From a user experience perspective, I want to automatically generate certificates when my proxy starts, and trust those. This will mean that each run of the proxy will have new certificates.

Looks like the rust openssl library has a builder struct that I can hopefully use without too much trouble. To use that, I added openssl = "0.10" to my Cargo.toml. The build didn’t even have to re-download anything, so I was probably pulling in that dependency anyway.

I ended up searching for x509builder through all of the rust projects in github advanced search, and ended up right back at the function that the proxy library I’m using calls to generate its certs. Now I just have to figure out how to get them.

Well, unfortunately it looks like this proxy generates certificates on demand to pose as whatever domain the client happens to be requesting since it doesn’t know up front what domains it will need to impersonate. That makes sense, but I’ll definitely have to change that. I know already that I want to pretend to be the AWS endpoints.

I may be able to do something kind of obnoxious to avoid doing the work though. It looks like the library caches the certs it has already generated. Maybe if I call that function, capture the result, and then output all that information, the library will return the same certificate every time that specific domain is requested. It’s worth a try.

Unfortunately, there’s no way this will be the full solution, because it generates a new cert for every full host, and there are many AWS service endpoints. I could self sign a cert that is valid for every single endpoint or do something with wildcards, but this is starting to seem wrong.

I think the right way to do this is to generate my own Self Signed Certificate Authority Certificate, trust it, pass it to the proxy, and have the proxy sign all its certificates with my custom CA. Then I can have it successfully pose as AWS and my clients on my system will trust all the certificates it generates in the process.

This will require some changes in that proxy library to actually support this.

Generating A Certificate Authority

All right, so now I’m in the world where I’m trying to create my own self signed CA. This is not where I wanted to be, but I’m here, so let’s see where it goes.

First, I can see that the X509Builder object that I was using before has no mention of CA certificate.

I know from a random conversation (not satisfying, I know) that CA certificates are different from normal certificates because you don’t want a random compromised certificate to suddenly give an attacker the ability to suddenly sign a bunch of other certificates. Here’s an example from the RFC of something that must be in CA certificates specifically.

I’m looking around and I see this code in the rcgen crate to generate a CA certificate, but that code looks a bit scary, and doesn’t use what I thought was the main rust openssl library.

I don’t really want to use some random library here if I can help it, and unfortunately I just found this issue talking about what I assume is the main rust openssl library not even having the ability to sign certificates using another certificate. That might actually kill this.

Back to Basics

Ultimately, I want to start with something that I know works, and go up from there. This situation right now where everything is wide open and I have no starting point isn’t great.

Once I have a working example, then I can start to do fancy stuff, like having everything auto generated. Plus, I’ll be able to compare what I generate to something that I know works, using openssl commands that look something like this:

$ echo | openssl s_client -showcerts -servername \
    -connect 2>/dev/null | \
    openssl x509 -inform pem -noout -text
        Version: 3 (0x2)
        Serial Number:
    Signature Algorithm: sha256WithRSAEncryption
    ... etc. ...
            X509v3 Subject Alternative Name: 
      ,,, DNS:*
    ... etc. ...

I could actually go through the whole process with the openssl tool, but I know from experience that’s a huge pain with a lot of magic configuration options and files everywhere, and I don’t wanna. If I did, this post actually seems like a great example of how.

Instead, I’m going to see if anyone has created tools I can use that will make it easier to do this with a sane interface. I heard about mkcert and cfssl from friends and previous projects, so let’s try those. I also found pkictl which looks like it might be decent, but it also still looks too openssl.

The mkcert tool looks like it might be a good place to start, because it’s meant to simplify generating development certificates, and it actually automatically trusts the CA that it generates, which saves me some effort.

Using mkcert

First, let’s follow the Quickstart:

$ go run -install "*" "*"
Using the local CA at "/home/sverch/.local/share/mkcert" ✨

Created a new certificate valid for the following names 📜
 - "*"
 - "*"

Reminder: X.509 wildcards only go one level deep, so this won't match ℹ️

The certificate is at "./" and the key at "./" ✅

Note, this required root permissions and asked for my root password the first time I ran this, but since this code is out in the open I trust that it’s unlikely to be malicious. Better than piping to a shell.

All right, so we have a certificate already!

$ openssl x509 -text -noout -in 
        Version: 3 (0x2)
        Serial Number:
    Signature Algorithm: sha256WithRSAEncryption
        Issuer: O = mkcert development CA, OU = sverch@hawking (Shaun Verch), CN = mkcert sverch@hawking (Shaun Verch)
            Not Before: Jun  1 00:00:00 2019 GMT
            Not After : Oct 26 05:29:19 2029 GMT
        Subject: O = mkcert development certificate, OU = sverch@hawking (Shaun Verch)
            ... etc. ...
            X509v3 Subject Alternative Name: 
                DNS:*, DNS:*
            ... etc. ...

Great. So I have a CA that mkcert installed, and a certificate signed by that CA. Now let’s try to shove it into the proxy.

Adding It To The Proxy

It looks like this is the line of code that I would need to change. Instead of generating a certificate each time, I could support passing in a certificate.

Unfortunately, that would require changing the library itself and then pulling that into my proxy, and I’ve run out of time for today.

Next Time

Well, this was kind of a mess, but I shouldn’t be surprised when digging into the world of certificates that things get a little crazy. Here’s what I’ve learned:

  • There are system wide global trust stores that are mostly standard, and will probably be good enough. If I find a misbehaving language or tool, I’m okay with dealing with them on a case by case basis.
  • At the very least I want to generate a CA to use to sign my certificates, because I want to trust that CA rather than have everything be self signed.
  • Doing all of this in rust seems like it would be a lot of effort and doesn’t have the library support yet.
  • The mkcert tool might get me pretty far in the short term.
  • The proxy library I’m using will have to be modified to support any of this.

Given all that, I think next time I’ll try to modify the proxy library to return the certs generated by mkcert, probably by providing an option to use a cert file instead of generating its own (then I’m not doing anything mkcert specific). Then, I can quickly test to see if curl trusts the certs and I don’t have to pass --insecure anymore, which will at least prove that part is hooked up.

At that point I’m free to start actually generating OpenAPI client libraries, because I have options to make them trust the cert (if they don’t already trust it because of the system store).