Who Designed This? A Deep Dive Into Ping Federate’s Maze of Misery

You ever stare at an “Access Token Invalid” error for 3 hours, only to realize the JWT claim wasn’t missing — it just wasn’t included in the default Ping policy unless you sacrificed a chicken under a full moon?

Because I have.

I’ve just come out the other side of integrating PingFederate + PingAuthorize to issue EC-signed JWTs for Snowflake OAuth client credentials flow.

It took me:

  • 30+ screenshots
  • 6 document versions
  • 3 complete rebuilds of policy trees
  • and a signed token that still somehow didn’t include scp despite explicitly defining it 5 different ways

What Should’ve Taken 2 Hours Took 2 Days

Let me be brutally clear: setting up Client Credentials Flow should not feel like doing a doctoral thesis in Authorization XML. But with Ping? It’s like wrestling a snake made of drop-down menus and hidden dependencies.

Here’s what I went through:

  • Infinite policy recursion: I evaluated the same policy from 4 layers deep and still got an empty access token.
  • No defaults, no fallbacks: If you forget to bind your attribute to a resolver and then call it from a tree, inside a statement, inside a scope condition, congrats — the token will just ignore you.
  • ES256 Signing? Cool. But what if the JWKS URI suddenly returns nothing unless the key is active AND marked default AND exposed? Hope you like toggling checkboxes in four different tabs with no warning.

PingFederate UX Is an Escape Room

Every screen is a trap:

  • The UI is inconsistent.
  • Labels don’t match docs.
  • You have to click into “Details” > “Modify” > “Advanced” just to find basic claim injection logic.

God forbid you want to include both sub and upn. Because unless you build a nested policy that resolves scopes, checks the client ID, and custom-serializes each claim into a payload block, you’re going to get a token with exactly one thing: a timestamp and your broken dreams.

The Best Part?

I finally got a working token. I decoded it, tears in my eyes. The payload was correct. It passed into Snowflake. But I didn’t feel proud. I felt robbed.

Robbed of a week of work.
Robbed of all the time I spent trying to extract logic from screenshots like they were cave paintings.
Robbed by a system that could be great, but fights you every single step of the way.

Here’s What I Learned (So You Don’t Suffer Like I Did)

  1. Never trust the UI. Export XML and grep it like you’re in 2003.
  2. Manually test token scopes using curl and JWT decode — trust nothing inside Ping.
  3. Document everything. Because next week, your working token will stop working, and no one knows why.
  4. Sign your own tokens with your own key and validate the claims manually. Because relying on Ping to do what it says it will do is like hiring a mime to narrate your audiobook.