jobtrackingapp/.gsd/milestones/M001/M001-ROADMAP.md

M001: Gmail and draft quality loop

Vision: Turn the existing job tracker into a daily-use personal job-search workspace where Gmail import and AI drafting are strong enough to trust, while preserving manual control over all real-world sending and applying.

Success Criteria

• User can import a job found elsewhere, generate a tailored CV and cover-letter package that feels specific enough to start from, and save/edit that package inside the job workspace.
• User can connect Gmail, import the right message or thread into a job with less cleanup than before, and see the imported correspondence reflected in that job’s timeline/workspace.
• User can generate a follow-up or reply draft grounded in the imported correspondence and saved job/application context.
• The daily loop of job table → follow-up/dashboard → individual job workspace feels coherent and actionable for an individual user.
• No part of the milestone auto-sends email or auto-applies to jobs.

Key Risks / Unknowns

• Gmail import may still feel unreliable if matching and import clarity do not improve enough to reduce manual cleanup.
• AI draft quality may still feel generic even though the draft surfaces already exist.
• The workflow may remain fragmented if table/dashboard/job-detail changes do not land as one coherent loop.
• Real value may depend on live Gmail + AI + persisted job context wiring, not isolated endpoint improvements.

Proof Strategy

• Gmail import reliability and trust → retire in S01 by proving a user can connect Gmail, review likely messages or threads for a job, and import the right correspondence into that job with clearer matching behavior.
• AI draft quality and usefulness → retire in S02 by proving imported job context plus profile/CV context produce tailored drafts the user can edit and save as actual working material.
• Reply/follow-up assistance grounded in real context → retire in S03 by proving imported correspondence and saved draft state feed a useful reply/follow-up drafting flow.
• Workflow coherence across daily surfaces → retire in S04 and S05 by proving the table/dashboard/job workspace work as one control loop and by re-checking the whole loop end-to-end.

Verification Classes

• Contract verification: backend/frontend tests, artifact checks for new endpoints and UI flows, persisted state checks, import/draft wiring verification
• Integration verification: real Gmail OAuth/import plus live AI-service-backed draft generation exercised through the app
• Operational verification: repeated use of the workflow across auth/config/service boundaries without dangerous outbound automation
• UAT / human verification: whether Gmail import feels trustworthy and whether drafts feel strong enough to start from in real use

Milestone Definition of Done

This milestone is complete only when all are true:

• all slice deliverables are complete
• Gmail import, correspondence state, and draft-generation surfaces are actually wired together
• the real browser entrypoint exists and is exercised through the table/dashboard/job loop
• success criteria are re-checked against live behavior, not just artifact presence
• final integrated acceptance scenarios pass

Requirement Coverage

• Covers: R001, R002, R003, R004, R005, R006, R007, R008, R010
• Partially covers: R009
• Leaves for later: R011, R012, R013
• Orphan risks: none

Slices

• S01: Smarter Gmail import and matching risk:high depends:[]

  After this: User can connect Gmail, review likely messages or threads for a job, and import correspondence with much better matching confidence and less manual cleanup.

• S02: Stronger AI application package drafting risk:high depends:[S01]

  After this: From an imported job plus profile/CV context, the app generates materially better tailored CV and cover-letter drafts that feel specific and usable.

• S03: Reply and follow-up drafting from real thread context risk:medium depends:[S01,S02]

  After this: Inside a job, the user can generate follow-up and reply drafts grounded in imported correspondence and saved application context, then edit them before sending manually.

• S04: Daily control loop surfaces risk:medium depends:[S01,S03]

  After this: The job table works as the primary overview and the follow-up/dashboard surfaces clearly show what needs attention next for an individual user.

• S05: End-to-end trust and workflow polish risk:low depends:[S01,S02,S03,S04]

  After this: The full loop works cleanly in a real environment: import job → generate package → apply externally → import/update correspondence → draft follow-up/reply → track progress confidently.

Boundary Map

S01 → S02

Produces:

• improved Gmail import workflow in job-tracker-ui/src/components/Correspondence.tsx that yields job-linked imported correspondence with clearer message/thread selection behavior
• stronger backend correspondence import surface in JobTrackerApi/Controllers/GmailController.cs and related persistence so imported messages reliably attach to JobApplication records
• stable job/correspondence linkage that later draft-generation flows can consume as trusted context

Consumes:

• nothing (first slice)

S01 → S03

Produces:

• imported correspondence records tied to a specific job and available through the existing per-job correspondence/timeline surfaces
• message/thread metadata good enough for later reply/follow-up draft context assembly
• a verified Gmail connection/import path that downstream slices can rely on

Consumes:

• nothing (first slice)

S02 → S03

Produces:

• improved application package generation via JobTrackerApi/Controllers/JobApplicationsController.cs returning stronger tailored CV and cover-letter outputs tied to a job
• persisted draft state in the job workspace so later follow-up/reply flows can reuse saved application context
• clearer frontend editing/saving behavior in job-tracker-ui/src/components/JobDetailsDialog.tsx

Consumes from S01:

• imported correspondence and job-linked message context

S03 → S04

Produces:

• reply/follow-up draft flow grounded in job + correspondence + saved application package context
• explicit manual-send boundary in the job workspace UI and backend behavior
• job-level indicators that a follow-up/reply is ready, missing context, or needs action

Consumes from S01:

• Gmail-imported correspondence context

Consumes from S02:

• saved tailored CV / cover-letter / application package context

S04 → S05

Produces:

• table/dashboard surfaces that summarize readiness, follow-up urgency, and next actions for individual users
• clearer navigation hierarchy across table, follow-up/dashboard, and individual job workspace
• stable daily-use control loop to validate in final integration

Consumes from S01:

• correspondence state and Gmail import outcomes

Consumes from S03:

• follow-up/reply drafting signals and job-level action state