Boomerang for Gmail

Build the following focused alternative to Boomerang for Gmail. This is a deliberately limited personal or small-team substitute, not parity with the paid service.

WORKING SLICE
Schedule a reviewed draft and remind its owner only if no matching reply arrives before a chosen deadline.

SETUP AND ARCHITECTURE
Use TypeScript, Node, PostgreSQL and a database-backed job worker with a small React run inspector. Prerequisites: Credentials for only the chosen integrations, their current API documentation, example payloads and an always-on worker for schedules. Before integrating anything, record actual versions and permissions, plus model files or provider limits only where used, in the README; make unavailable dependencies visible rather than simulating success.

DOMAIN MODEL AND INVARIANTS
Store DraftRevision, SendAttempt, ThreadReference and FollowUpRule; use message/thread identifiers and reply relationships rather than subject text alone to decide whether to cancel a reminder.

IMPLEMENTATION CONTRACT
Persist trigger identity, step input version and external receipts before marking success. Retry bounded transient failures; unknown write outcomes require reconciliation. Do not promise exactly-once execution across external services. Provide an input/setup view, the main work view, and a review/export view appropriate to this workflow. Preserve the last saved state if a job or save fails. Include empty, loading, permission-denied, partial and retryable-error states. Log identifiers and error categories without secret values or unnecessary private content.

APP-SPECIFIC BOUNDARY AND RECOVERY
Use one authorized mailbox adapter; show that local schedules stop when the worker stops. An ambiguous SMTP/API result requires reconciliation, and inbox pausing is deferred.

ACCEPTANCE SCENARIO
Receive an unrelated email with the same subject and then a true reply; the unrelated email leaves the reminder intact and the real reply cancels it. Also reopen the app after an interrupted operation, confirm the saved record/export remains inspectable, and document the recovery action. These are implementation acceptance requirements, not a claim that this guide has been tested.

DELIVERY
Deliver a runnable repository with migrations or project-format versioning, a non-sensitive example, environment/permission setup, the exact manual acceptance steps, and a backup/export-and-restore walkthrough. Implement the working slice before optional integrations; list any deferred paid-product capabilities honestly. Do not add capabilities outside the working slice just to resemble the original product.

PROJECT RULES FOR AGENTS.md
Keep the domain invariants above executable at the write boundary. Propose scope changes before adding providers or permissions. Never fabricate source evidence, publish results, identity matches or successful delivery. Preserve user originals and require an explicit confirmation for destructive changes or external publication.

# AGENTS.md — Build guide for Boomerang for Gmail

## Project scope
Schedule a reviewed draft and remind its owner only if no matching reply arrives before a chosen deadline.

Catalogue verdict: kinda. The visible Gmail scheduling add-on loop is buildable, but a credible replacement needs more than the first screen. Boomerang for Gmail earns its keep through deliverability, security, integration, so expect a weekend or multi-day build and a narrower personal scope.
Use the implementation prompt below to define the deliverable. Complete each phase's acceptance checks before extending the scope.

## Working agreement
- Inspect the repository and its existing instructions before choosing paths, dependencies or commands. Keep one coherent stack and explain changes to the proposed architecture.
- Plan a vertical slice that accepts a real input and produces the useful output described below. Persist only the state the prompt calls for; respect memory-only and upstream-managed workflows. Use fixtures only when they are clearly labelled.
- After scaffolding, document the actual install, development, check and build commands in README and keep them synchronized with the package or project manifest. Do not report commands as successful unless they ran.
- Work in small steps. At handoff, list implemented flows, checks actually performed, remaining blockers, and any credentials or provider setup the owner must supply.
- Do not publish, spend money, contact customers, delete source data or run irreversible migrations without the project owner's authorization.

## Prerequisites
- Runtime and tools: TypeScript, Node, PostgreSQL and a database-backed job worker with a small React run inspector.
- Before starting: Credentials for only the chosen integrations, their current API documentation, example payloads and an always-on worker for schedules.

## Stack and architecture
- TypeScript, Node, PostgreSQL and a database-backed job worker with a small React run inspector
- Data design: Store DraftRevision, SendAttempt, ThreadReference and FollowUpRule; use message/thread identifiers and reply relationships rather than subject text alone to decide whether to cancel a reminder.
- Setup: Credentials for only the chosen integrations, their current API documentation, example payloads and an always-on worker for schedules

## Security and data integrity
- Persist trigger identity, step input version and external receipts before marking success. Retry bounded transient failures; unknown write outcomes require reconciliation. Do not promise exactly-once execution across external services.
- Use one authorized mailbox adapter; show that local schedules stop when the worker stops. An ambiguous SMTP/API result requires reconciliation, and inbox pausing is deferred.
- Keep secrets outside client bundles and exported projects; document what leaves the device and make retention/deletion controls visible.

## Agent implementation rules
- Project rule — domain: Store DraftRevision, SendAttempt, ThreadReference and FollowUpRule; use message/thread identifiers and reply relationships rather than subject text alone to decide whether to cancel a reminder.
- Project rule — scope and recovery: Use one authorized mailbox adapter; show that local schedules stop when the worker stops. An ambiguous SMTP/API result requires reconciliation, and inbox pausing is deferred.
- Project rule — acceptance: Receive an unrelated email with the same subject and then a true reply; the unrelated email leaves the reminder intact and the real reply cancels it.
- Project rule — delivery: document real setup commands and permissions; do not claim a build, accuracy level, performance result or security certification that has not been demonstrated.

## Optional agent skills and references
- Recommended skill: [supabase-postgres-best-practices](https://github.com/supabase/agent-skills/blob/main/skills/supabase-postgres-best-practices/SKILL.md) — review this PostgreSQL domain schema, uniqueness constraints, transaction boundaries and access-scoped queries; Supabase hosting is not required. Follow the maintainer's installation instructions and match its requirements to the chosen runtime.
- Recommended skill: [sharp-edges](https://github.com/trailofbits/skills/blob/main/plugins/sharp-edges/skills/sharp-edges/SKILL.md) — review configuration and API defaults against the app-specific invariants and recovery boundaries above; this is not a security certification. Follow the maintainer's installation instructions and match its requirements to the chosen runtime.

Read the linked SKILL.md and its dependencies before adding a skill. Select only the skills matching this project's runtime and task; their documentation does not supply API access, credentials or approval to perform external actions. Pin the reviewed revision where the tool supports it. Follow the chosen agent's documented project-level installation mechanism.

## Distribution ideas
These are optional planning notes. Obtain the owner's approval before publishing or contacting anyone.
- Demonstrate this working slice using synthetic or explicitly authorized non-sensitive examples: Schedule a reviewed draft and remind its owner only if no matching reply arrives before a chosen deadline.
- Share a synthetic example export and the acceptance walkthrough; keep real customer, health, financial and source data private: Receive an unrelated email with the same subject and then a true reply; the unrelated email leaves the reminder intact and the real reply cancels it.
- State the limits before asking someone to replace their existing tool: Use one authorized mailbox adapter; show that local schedules stop when the worker stops. An ambiguous SMTP/API result requires reconciliation, and inbox pausing is deferred.

## Engineering roadmap
1. Phase 1 — Pin the working slice and create its example input: Schedule a reviewed draft and remind its owner only if no matching reply arrives before a chosen deadline. Confirm setup: Credentials for only the chosen integrations, their current API documentation, example payloads and an always-on worker for schedules.
2. Phase 2 — Implement persistence and write-time invariants before decorating the UI: Store DraftRevision, SendAttempt, ThreadReference and FollowUpRule; use message/thread identifiers and reply relationships rather than subject text alone to decide whether to cancel a reminder.
3. Phase 3 — Connect the working view to real saved state. Persist trigger identity, step input version and external receipts before marking success. Retry bounded transient failures; unknown write outcomes require reconciliation. Do not promise exactly-once execution across external services.
4. Phase 4 — Expose the app-specific limits and recovery path in context: Use one authorized mailbox adapter; show that local schedules stop when the worker stops. An ambiguous SMTP/API result requires reconciliation, and inbox pausing is deferred.
5. Phase 5 — Walk through this concrete acceptance case and preserve its exported evidence: Receive an unrelated email with the same subject and then a true reply; the unrelated email leaves the reminder intact and the real reply cancels it. Finish the README and backup/restore instructions; report unfinished capabilities explicitly.

## Paid-product capabilities outside this build
- team routing and shared inbox rules
- abuse response and security operations
- calendar-provider edge cases and timezone correctness
- provider-grade deliverability
- push reliability across devices

## Implementation prompt
Build the following focused alternative to Boomerang for Gmail. This is a deliberately limited personal or small-team substitute, not parity with the paid service.

WORKING SLICE
Schedule a reviewed draft and remind its owner only if no matching reply arrives before a chosen deadline.

SETUP AND ARCHITECTURE
Use TypeScript, Node, PostgreSQL and a database-backed job worker with a small React run inspector. Prerequisites: Credentials for only the chosen integrations, their current API documentation, example payloads and an always-on worker for schedules. Before integrating anything, record actual versions and permissions, plus model files or provider limits only where used, in the README; make unavailable dependencies visible rather than simulating success.

DOMAIN MODEL AND INVARIANTS
Store DraftRevision, SendAttempt, ThreadReference and FollowUpRule; use message/thread identifiers and reply relationships rather than subject text alone to decide whether to cancel a reminder.

IMPLEMENTATION CONTRACT
Persist trigger identity, step input version and external receipts before marking success. Retry bounded transient failures; unknown write outcomes require reconciliation. Do not promise exactly-once execution across external services. Provide an input/setup view, the main work view, and a review/export view appropriate to this workflow. Preserve the last saved state if a job or save fails. Include empty, loading, permission-denied, partial and retryable-error states. Log identifiers and error categories without secret values or unnecessary private content.

APP-SPECIFIC BOUNDARY AND RECOVERY
Use one authorized mailbox adapter; show that local schedules stop when the worker stops. An ambiguous SMTP/API result requires reconciliation, and inbox pausing is deferred.

ACCEPTANCE SCENARIO
Receive an unrelated email with the same subject and then a true reply; the unrelated email leaves the reminder intact and the real reply cancels it. Also reopen the app after an interrupted operation, confirm the saved record/export remains inspectable, and document the recovery action. These are implementation acceptance requirements, not a claim that this guide has been tested.

DELIVERY
Deliver a runnable repository with migrations or project-format versioning, a non-sensitive example, environment/permission setup, the exact manual acceptance steps, and a backup/export-and-restore walkthrough. Implement the working slice before optional integrations; list any deferred paid-product capabilities honestly. Do not add capabilities outside the working slice just to resemble the original product.

PROJECT RULES FOR AGENTS.md
Keep the domain invariants above executable at the write boundary. Propose scope changes before adding providers or permissions. Never fabricate source evidence, publish results, identity matches or successful delivery. Preserve user originals and require an explicit confirmation for destructive changes or external publication.

## Completion evidence
Demonstrate the prompt's acceptance scenarios against the scoped workflow. Include setup from a clean checkout and failure recovery. Check persistence across restart and export/restore only for the state the prompt says to store; for memory-only tools, confirm that temporary content is discarded as specified. Record actual results and remaining limitations. A detailed plan alone does not establish a working replacement.