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Protocols20 March 2026·3 min read

Azure Entra nested groups and Directory Sync: Limitations and workarounds

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.

The problem: SCIM doesn't know about nested groups

That brings us to the problem: scim doesn't know about nested groups. 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.

What this looks like in practice

What this looks like in practice 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

Three patterns that actually work

Consider three patterns that actually work. 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.

Flatten the group membership

Consider flatten the group membership. 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.

Assign child groups directly to the application

Assign child groups directly to the application 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.

Supplement SCIM with the Microsoft Graph API

That brings us to supplement scim with the microsoft graph api. 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.

How this compares to Google Workspace

That brings us to how this compares to google workspace. 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.

Where this leaves us

None of this is exotic. It is the ordinary discipline of deciding what you own, writing down what you assume, and making the failures loud enough to notice.

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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