AI Pre-Send Email GuardDog MVP

BCcGuardDog is a lean MVP that quietly sits inside Gmail / Google Workspace and, the moment I hit “Send”, double-checks the recipient list with AI. Its single, clear job right now is to warn me when someone who logically belongs on the thread is missing—no auto-sorting, no reply drafting, just this pre-send safety net.

The flow I picture:
• Intercept the Gmail send event (Add-on, Chrome extension or other sanctioned method).
• Pass sender, recipients, subject and thread history through a lightweight model or ruleset that spots anomalies such as “Manager was on every prior message but is now gone”.
• Surface an in-context modal that explains the potential oversight and lets me cancel or continue.
• Log decisions so the system learns and reduces false positives over time.

Acceptance criteria for this MVP
1. Works on both consumer Gmail and Google Workspace accounts I provide for testing.
2. Triggers within one second of pressing Send and never blocks a send when the user selects “Send anyway”.
3. Accuracy: in a curated test set of 50 messages, it must flag at least 80 % of truly missing-recipient cases and produce no more than 10 % false positives.
4. Clean uninstall with no lingering permissions.

I’m happy with Node.js or Python for cloud logic, Google Apps Script for rapid prototyping, and OpenAI or a small local model for inference—choose the stack you ship fastest with, as long as Google’s OAuth and Gmail API guidelines are respected.

This is needed ASAP, so please outline how many days you need for a functional demo and how you’ll meet the acceptance criteria above.