[BUG] MCP connector 'Always allow' ignored on individual Pro plan

Summary

On my individual Pro plan, the "Always allow" setting for personal MCP connectors (Gmail, Google Workspace) is not persisted — every tool call still triggers an approval prompt. On a separate Team plan account belonging to the same user, with the same connectors and the same Projects-based workflow, "Always allow" works correctly.

This is the opposite of #19731 (which framed the same symptom as Team-Plan-only). Posting per the auto-close message on #19731 ("please file a new issue and reference this one if it's relevant").

Reproduction (individual Pro plan)

1. Install personal MCP connectors (e.g. Gmail, Google Workspace) at Settings → Connectors
2. Set them to "Always allow"
3. Open a chat in a Project
4. Use a connector tool → approval prompt appears
5. Approve with "Always allow"
6. Use the same tool later (new chat in same Project, or same chat after a delay) → tool prompts for approval again

Expected

Per the Settings → Connectors UX, "Always allow" should persist across chats and Projects without re-prompting.

Actual

Approval prompt appears for every tool call. If the user is AFK when the prompt fires, it eventually times out and the tool call fails with No approval received.

Secondary bug: misleading error message

No approval received is indistinguishable from an OAuth/auth failure to the user (and to other Claude assistants helping diagnose — I had one tell me to reconnect the connector at Settings → Connectors, which obviously didn't fix anything). Suggest distinguishing "user did not approve in time" from "connector auth is broken" in the surfaced error string.

Comparison data point (potentially useful for triage)

Same user, same connectors (functionally equivalent), same Projects-only workflow:

• Individual Pro plan account (personal-installed connectors): bug reproduces ❌
• Team plan account (org-managed connectors at org admin level): works correctly ✅

This is the inverse of what #19731 reports. The split suggests the bug is in the per-user / personal-connector permission-persistence path, not the org-managed connector path.

Environment

• claude.ai web interface
• Confirmed 2026-05-06 (recurring for at least the prior 2 days)
• All chats are inside Projects

References

• #19731 — same symptom, framed as Team-Plan-only, closed stale 2026-02-27, auto-locked 2026-03-08
• #28580 — MCP tools prompt for permission even when already authorized
• #8859 — Post-outage permission regression