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Authentication and SSO4 min read

Best practices for CLI authentication: A technical guide

It is easy to read a specification and conclude the problem is solved.

It is easy to read a specification and conclude the problem is solved. It is harder to sit with the twenty implementations that each read the same paragraph differently and still call themselves compliant.

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

Common CLI authentication patterns

That brings us to common cli authentication patterns. 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.

API keys and credentials files

API keys and credentials files 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.

  • 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

Browser-based OAuth flow

Browser-based OAuth flow 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.

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.

Device Code Flow

Device Code Flow 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.

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.

Treat anything the other side sends as untrusted input until it has been through validation you wrote.

Username/Password with Token Exchange

Username/Password with Token Exchange deserves its own treatment. 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.

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.

Token storage and security

That brings us to token storage and security. 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.

System keychains

System keychains 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.

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.

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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