v1.6.39 / Pipedrive: AI Assistant auto-start fails ~50% of calls, and SMS never logs to CRM

Two separate issues with App Connect v1.6.39 on the Pipedrive connector. Account ID 2752252027.

Setup: Chrome, RingEX, Super Admin. Preferred device is set to Browser. Verified enabled: AI Assistant (Beta), Auto-start AI Assistant (Beta), Log phone calls automatically, Log SMS conversations automatically, Retroactive call log sync, One-time call logging, Smart summary, Call transcript.

ISSUE 1 - AI Assistant fails to auto-start on roughly half of calls

Placing a call via click-to-dial from a Pipedrive contact intermittently shows: "Failed to auto start AI assistant, please start it manually after call answered"

About a 50% failure rate across 8 consecutive calls in one session, same path and same settings with no changes between attempts. Clicking Start manually after the call is answered works every time, and the notes and transcript then log to Pipedrive correctly.

Already ruled out: preferred device is already Browser, all relevant toggles verified on, reproduced with the Chrome debugger fully detached, and the page reloaded after every settings change.

ISSUE 2 - SMS never logs to Pipedrive

Multiple outbound SMS sent from the App Connect widget (message icon on a Pipedrive contact's number). All confirmed Delivered in the RingCentral admin SMS Log. None appear on the matching Pipedrive contact record.

The useful comparison: eight calls placed to that same number on that same contact the same evening all logged successfully with full AI notes and transcripts. Calls log every time, SMS logs never. Contact matching clearly works, it just is not being applied on the SMS path.

That contact also holds an SMS Sent activity from 13 August created by our previous phone provider, so Pipedrive accepts SMS activity on the record.

One detail that may help: the admin SMS Log shows "Add Contact" next to the recipient number, which suggests the number is not being resolved to a known contact on the SMS path specifically.

Note on diagnostics: the downloaded error log is empty. Neither failure produces a logged error, even though the auto-start failure surfaces a user-facing error message. Happy to capture browser console output or run whatever diagnostic would be more useful.

Questions:

1. Is the auto-start failure known, and is a fix planned?

2. Is either issue resolved in App Connect 2.0, or should we stay on 1.6.x?

3. Is the SMS logging failure specific to the Pipedrive connector?