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Protocols27 April 2026·3 min read

How to handle JWT in Ruby

Protocol work looks tedious from the outside and turns out to be where the interesting failures live.

Paycux engineering

Protocol work looks tedious from the outside and turns out to be where the interesting failures live. The specification is short; the space of things implementers actually ship is not.

This piece walks through how we think about it at Paycux, what we have changed our minds about, and where the sharp edges are.

JWT 101

JWT 101 is where this gets concrete. Version the assumption, not just the code. Write down what you expect from the peer, and make the failure loud when it stops being true, because the alternative is a connection that half works for six weeks.

Normalization is the whole job. Two providers can be perfectly compliant and still disagree about what a group membership is, whether a logout is meaningful, and which attribute carries the email address.

Header

Header deserves its own treatment. Treat anything the other side sends as untrusted input until it has been through validation you wrote. Signature checks, issuer checks, audience checks and expiry checks are four separate decisions, and skipping any one of them is a real vulnerability rather than a theoretical one.

Normalization is the whole job. Two providers can be perfectly compliant and still disagree about what a group membership is, whether a logout is meaningful, and which attribute carries the email address.

  • Validate signature, issuer, audience and expiry as four separate checks
  • Normalize provider attributes into one internal shape
  • Fail loudly when a peer stops meeting a documented assumption
  • Keep a fixture per provider so regressions surface in CI

Payload

Consider payload. Version the assumption, not just the code. Write down what you expect from the peer, and make the failure loud when it stops being true, because the alternative is a connection that half works for six weeks.

Treat anything the other side sends as untrusted input until it has been through validation you wrote. Signature checks, issuer checks, audience checks and expiry checks are four separate decisions, and skipping any one of them is a real vulnerability rather than a theoretical one.

Signature

That brings us to signature. Normalization is the whole job. Two providers can be perfectly compliant and still disagree about what a group membership is, whether a logout is meaningful, and which attribute carries the email address.

Version the assumption, not just the code. Write down what you expect from the peer, and make the failure loud when it stops being true, because the alternative is a connection that half works for six weeks.

Normalization is the whole job.

JWT library for Ruby

That brings us to jwt library for ruby. Normalization is the whole job. Two providers can be perfectly compliant and still disagree about what a group membership is, whether a logout is meaningful, and which attribute carries the email address.

Version the assumption, not just the code. Write down what you expect from the peer, and make the failure loud when it stops being true, because the alternative is a connection that half works for six weeks.

Generating your keys

Generating your keys deserves its own treatment. Normalization is the whole job. Two providers can be perfectly compliant and still disagree about what a group membership is, whether a logout is meaningful, and which attribute carries the email address.

Normalization is the whole job. Two providers can be perfectly compliant and still disagree about what a group membership is, whether a logout is meaningful, and which attribute carries the email address.

Generating an RSA key pair and JWK in Ruby

Generating an RSA key pair and JWK in Ruby is where this gets concrete. Version the assumption, not just the code. Write down what you expect from the peer, and make the failure loud when it stops being true, because the alternative is a connection that half works for six weeks.

Normalization is the whole job. Two providers can be perfectly compliant and still disagree about what a group membership is, whether a logout is meaningful, and which attribute carries the email address.

Where this leaves us

The pattern repeats across every system we have looked at: the hard part is not the mechanism, it is keeping the mechanism honest as the surrounding assumptions change.

If you are working through the same problem and want to compare notes, the docs cover the mechanics and the console shows the behaviour on your own data.

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