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Addresses the two issues Elon raised on #3360. Must-fix: if the PAT is already revoked/expired when the daemon starts, syncWorkspacesFromAPI 401s and Run returns before the background tokenRenewalLoop ever fires its initial renewal. The operator only sees a generic auth failure in the workspace-sync log with no hint that 'multica login' is the fix. Now the startup path runs an inline tryRenewToken first, surfacing the existing 401 WARN before anything else gets a chance to fail. Pulled the renew + first-sync pair into preflightAuth so the ordering invariant is enforced at one site and tests can exercise the failure modes without spinning up the full Run setup. Removed the redundant initial tryRenewToken from tokenRenewalLoop — startup now owns the first call. Nit: the previous WHERE clause on ExtendPersonalAccessTokenExpiry (expires_at < $2) did not actually make concurrent renews idempotent the way the comment claimed. Two callers race-computing $2 = now + 90d produce strictly-different values, and the second writer's $2 always exceeds the row the first writer just wrote, so the UPDATE re-matches and bumps again. Switched to a CAS against the renewal threshold (expires_at <= $renew_threshold_at, i.e. now + 7d): once writer A pushes expires_at past the threshold, writer B's UPDATE matches zero rows and the loser falls back to reporting the already-extended value as a no-op. Tests: - TestPreflightAuth_RenewsBeforeWorkspaceSyncOnExpiredToken locks in the call ordering — renew endpoint is hit before workspaces, and the re-login WARN appears even though both endpoints 401. - TestPreflightAuth_SyncProceedsWhenRenewIsNoOp covers steady-state startup: a renew=false no-op must still progress to workspace sync. - TestPreflightAuth_TransientRenewFailureDoesNotBlockStartup covers a 500 from the renew endpoint — startup must continue, no WARN. - TestRenewPAT_ParallelRenewExtendsExactlyOnce fires N=8 concurrent renews at one row and asserts exactly one returns renewed=true with the others reporting the same already-extended expires_at, plus the DB carries only that single bumped value. Co-authored-by: multica-agent <github@multica.ai>