M003: Deeper inbox-aware assistance — Context Draft

Gathered: 2026-03-24 Status: Draft — needs milestone-specific discussion before planning

Seed from broader discussion

After the first Gmail improvements, there is likely room to deepen inbox-aware assistance and correspondence-driven help. This should still remain assistive rather than autonomous, and it should continue to support an individual user’s job-search workflow instead of turning into broad automation for its own sake.

Intended milestone role

M003 likely extends the correspondence and assistance layer beyond the first trust milestone. The likely focus is richer inbox awareness, better use of message context over time, and additional AI help that stays grounded in real application history.

Likely capabilities

richer message/thread understanding after import
better context assembly from accumulated correspondence
broader assistance around replies, follow-up strategy, and ongoing job-specific communication
selective expansion of AI coaching only where it strengthens the core user loop

Constraints already known

no auto-send and no auto-apply remain hard boundaries
assistance should stay grounded in imported job/application/correspondence context
the product is still for one person managing their own search
the app should not drift into generic chatbot behavior

What this milestone unlocks

A more aware assistant that understands the state of an application thread over time and can help the user respond more intelligently without taking control away.

Open questions for future discussion

What additional inbox-aware behavior is actually high value after M001?
How much strategic coaching belongs here versus later?
Which parts of correspondence history should influence drafting most?
What privacy or trust surfaces need to become more visible as the assistant becomes more context-aware?

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