AI sessions
Troubleshoot agent connections
Updated July 25, 2026
Most agent connection problems are quiet ones - nothing errors, the agent just behaves like Milestone isn't there. This page maps each symptom to the piece that's actually failing.
Start by naming the symptom
| What you see | What's usually wrong |
|---|---|
| Agent has no Milestone tools | The connection isn't installed |
| Tools work, answers stay generic | Team knowledge sync is off |
| Answers come from another team | The token is from the wrong workspace |
| Work lands on the wrong board | The repo isn't bound, or is bound to another board |
| It worked yesterday, not today | The credential changed - restart your sessions |
The connection isn't installed
Go to Settings → Connections and check the status. Needs repair or Not installed both fix the same way: click Repair, then Recheck.
If it keeps reverting, make sure you're signed in and have a workspace selected - the connection can't be written without both.
Tools work, but nothing is remembered
Team knowledge sync is a separate switch and it's off by default. Turn on Enable on this machine under Team knowledge sync. If the switch is greyed out, the Claude Code connection isn't Healthy yet - fix that first.
Sync stays silent when it can't act
Knowledge sync only acts inside repositories that belong to your workspace. In an unbound repo it does nothing and says nothing - by design, so it never touches unrelated code. A quiet session in an unbound repo is expected.
So if sync is on and still quiet, check the repository before anything else: it needs a git remote, and it needs to be bound. See Bind a repo.
Changes don't take effect
claude and codex read their configuration once, at startup. If you repaired a
connection, regenerated a token, or turned on knowledge sync while a session was
open, that session is still using the old setup. Quit it and start a new one.
This is also true for Codex tool lists - a session that started before you connected won't show Milestone's tools until you restart it.
Answers come from the wrong workspace
Your workspace is baked into the token, so this isn't a setting you can toggle mid-session. Generate a new token from the correct workspace and replace the old one, then restart your sessions.
Still stuck
Get in touch with what you're seeing and which of the pieces above you've already checked.
Related
- How agent context works - what each piece does.
- Team knowledge sync.
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