Fixing the Intermittent License Nudge Bug in MemStack Pro

Had an interesting debugging session today with MemStack Pro. You know that feeling when something works most of the time but randomly fails? That's exactly what was happening with our license nudge feature.

The Mystery

Users were reporting that the license nudge wasn't showing up consistently during session startup. Sometimes it appeared, sometimes it didn't. Classic intermittent bug behavior that makes you question your sanity.

The Detective Work

I set up a multi-agent coordination approach using agent-bridge to tackle this. Had a Manager delegate the investigation to a Builder agent, who then sent findings to a Reviewer, and back to Builder for implementation. It's pretty cool how you can orchestrate different AI roles to handle complex debugging workflows.

The Builder agent quickly identified the root cause: we had three sequential SessionStart hooks running in settings.json. The license nudge was the third one in line, but the first two hooks (session-start.sh with a 10s timeout and session-context-load.sh with 15s timeout) were potentially exhausting the hook execution budget. When that happened, our poor little license nudge got skipped.

The Fix

The solution was elegantly simple. Instead of running the license nudge as a separate hook, I merged the logic directly into the end of session-start.sh - right before the exit 0. This eliminated the sequential timeout risk and reduced our SessionStart hooks from 3 groups down to 2.

The timing works out perfectly too. The nudge displays after the Headroom and indexing processes complete, so users get a clean experience.

Clean Up

After implementing the fix, I cleaned house by:

• Removing the standalone hook entry from settings.json
• Deleting the now-unnecessary session-start-license-nudge.sh file
• Getting reviewer confirmation that all changes were properly positioned

Committed everything as a4d89e8: fix: merge license nudge into session-start hook - eliminates intermittent display

Lessons Learned

This was a good reminder that sometimes the best architectural decision is the simpler one. Instead of having multiple moving parts that can fail independently, consolidating related functionality often leads to more reliable systems.

The multi-agent workflow was surprisingly effective for this kind of systematic debugging. Having different "perspectives" analyze the problem helped catch details I might have missed flying solo.