can-you-assist/workplans/CYA-WP-0003-contextual-memory-activation-and-retrospection.md

id, type, title, domain, repo, status, owner, topic_slug, created, updated, state_hub_workstream_id

id	type	title	domain	repo	status	owner	topic_slug	created	updated	state_hub_workstream_id
CYA-WP-0003	workplan	Contextual Memory Activation and Retrospection Loops for Continuous Optimization	capabilities	can-you-assist	active	grok	foerster-capabilities	2026-05-27	2026-05-27	ac9a9d42-4db9-44d0-9b41-5e16d87c65c8

CYA-WP-0003: Contextual Memory Activation and Retrospection Loops for Continuous Optimization

Goal

Build on the real memory foundation delivered in CYA-WP-0002 to make memory actively useful for context-aware assistance, with two primary advances:

1. Directory- and project-bound memory activation: Automatically and intelligently surface relevant memory when the user is working in a specific directory or project, without requiring explicit recall every time.
2. Regular retrospection loops: Enable structured, recurring reflection sessions between the user and cya that turn memory into a vehicle for continuous improvement — reviewing what worked, setting interaction goals, and evolving preferences over time.

This workplan directly addresses two remaining gaps identified in the post-0002 Intent-vs-Scope analysis:

• Moving from passive memory storage to proactive, contextually activated memory.
• Establishing the foundation for true longitudinal adaptation and a user-driven optimization loop.

Background & References

• INTENT.md — especially the "Personalized Console Helper" section and the explicit call for phase-memory to support "project-specific memory" and "recurring workflows".
• MemoryVision.md — defines primary memory kinds relevant to cya, including Project/Directory Memory and Workflow Recipes.
• history/2026-05-27-CYA-Intent-Scope-Gap-Analysis-Post-0002.md — identifies remaining gaps in contextual activation and longitudinal value after 0002.
• CYA-WP-0002 — delivered the real (persisting) memory implementation and explicit ports.
• Current memory ports in src/cya/memory/__init__.py (the scope parameter is the natural starting point for directory binding).
• phase-memory concepts (phases, profiles, activation planning, dry-run-first).

Non-Goals (for this slice)

• Full autonomous agentic behavior or background memory harvesting.
• Deep semantic understanding of code or notes (still out of scope).
• Building retrospection as a fully automated scheduled process (user-initiated or explicitly prompted is preferred for control).
• Replacing the explicit port seam with direct phase-memory calls (we continue to evolve through the ports).
• Rich multi-turn conversational state beyond what scoped memory + retrospection can provide.

Task Breakdown

T01 — Refine the conceptual model for contextual activation and retrospection loops

id: CYA-WP-0003-T01
status: done
priority: high
state_hub_task_id: "335595b4-96fe-401f-ab4c-0824a6ba3f05"
started: "2026-05-27 ralph iter 1"
completed: "2026-05-27"

Done — produced docs/cya-memory-activation-and-retrospection-concept.md.

• Deeply aligned the two ideas with INTENT.md (Personalized Console Helper, project-specific memory, recurring workflows, user control) and MemoryVision.md (Project/Directory Memory, Workflow Recipes, activation planning, explainability requirements).
• Defined clear models:
  • Memory Activation: Automatic, scope-aware (cwd + git root) surfacing of relevant items (preferences, patterns, safety signals) with strong provenance and user control.
  • Retrospection Loops: Deliberate reflection sessions that produce higher-order memory (interaction_goal, retrospection outcomes) which preferentially influence future activation and behavior.
• The two mechanisms reinforce each other: normal use generates candidates for retrospection; retrospection produces high-quality memory that improves future activation.
• Identified minimal port/data model extensions for T02 (richer kind support and activation hints in recall, standardized retrospection record kinds).
• Non-negotiables (explainability + safety invariants) explicitly preserved.

Acceptance criteria met:

• Clear, written concept document exists and is consistent with INTENT and MemoryVision.
• The ideas are shown to reinforce each other in a user-controlled continuous optimization loop.

T02 — Extend memory ports and data model for activation and retrospection

id: CYA-WP-0003-T02
status: todo
priority: high
state_hub_task_id: "6f50bdf4-6252-4b93-9697-407ef432cd90"

• Evolve the four ports (or add minimal new ones) to better support:
  • Richer scoping and activation hints (e.g., directory + project identity + optional profile).
  • Storing and retrieving "retrospection outcomes" and "interaction goals" as first-class memory.
• Define lightweight structures for retrospection records and activated context packages.
• Maintain full backward compatibility and user inspectability.

Acceptance criteria:

• Ports and data model support the concepts from T01 without breaking existing usage.
• All new memory remains fully user-visible and editable.

T03 — Implement directory- and project-bound memory activation

id: CYA-WP-0003-T03
status: todo
priority: high
state_hub_task_id: "45731b48-74a5-485b-bd56-72f387db3846"

• In the orchestrator (and context collection path), automatically activate relevant memory based on the current working directory and git root.
• Make activation smart but transparent: surface what was activated and why (especially via --explain-context).
• Allow users to influence activation (e.g., "always include these memories in this project").

Acceptance criteria:

• When working in a directory where preferences or patterns have been remembered, cya demonstrably uses them without the user having to restate them.
• Activation is visible and controllable.

T04 — Build the retrospection interaction flow

id: CYA-WP-0003-T04
status: todo
priority: high
state_hub_task_id: "fb63edc4-1e3f-4964-a2b6-19b29d00ffd8"

• Design and implement a retrospection mode or dedicated subcommand / prompt pattern.
• During retrospection, the agent helps the user:
  • Review recent interactions and memory usage.
  • Reflect on what helped or didn't.
  • Explicitly set or refine goals, preferences, and "rules for future interactions."
• Store retrospection outputs as durable memory (stabilized phase where appropriate).

Acceptance criteria:

• A user can run a retrospection session and have its outcomes affect future assistance.
• The flow feels natural in a terminal and respects user control.

T05 — Close the continuous optimization loop

id: CYA-WP-0003-T05
status: todo
priority: medium
state_hub_task_id: "f17a4f42-1630-4244-bdd4-c8d732e8de9b"

• Wire retrospection outcomes back into normal assistance flows (context building, explanation style, safety tuning, memory activation).
• Add basic mechanisms so that "interaction goals" set during retrospection measurably influence future behavior.
• Ensure the loop remains user-driven and auditable.

Acceptance criteria:

• After a retrospection session, subsequent cya interactions demonstrably reflect the user's stated goals and reflections.

T06 — Tests, observability, and graceful degradation

id: CYA-WP-0003-T06
status: todo
priority: high
state_hub_task_id: "c7da1a0d-647f-48d9-aba3-d2e62791e05f"

• Add comprehensive tests for activation logic, retrospection flows, and the closed optimization loop.
• Ensure strong observability (what memory was activated, what retrospection outcomes influenced a response).
• Verify graceful behavior when memory is unavailable or the user opts out of retrospection.

Acceptance criteria:

• New behaviors have solid test coverage.
• pytest remains clean with no new external dependencies for normal runs.

T07 — Documentation, examples, and handoff

id: CYA-WP-0003-T07
status: todo
priority: medium
state_hub_task_id: "d120efff-eaf6-4630-a3d3-3e70a3db4e09"

• Heavily update README with before/after examples of directory-bound activation and retrospection sessions.
• Document the new interaction patterns in AGENTS.md and MemoryVision.md.
• Register extension points and any new technical debt.
• Provide clear guidance for phase-memory owners on how retrospection data can flow into richer profiles.

Acceptance criteria:

• A reader can understand and try the new capabilities from the README alone.
• The concepts are clearly connected back to INTENT and MemoryVision.

Dependencies & Cross-Repo Coordination

• phase-memory: The concepts here are designed to be consumable and eventually enriched by richer phase-memory capabilities (profiles, phases, activation planning). Close coordination recommended during T01/T02.
• markitect-tool: May become relevant if retrospection outcomes or directory contexts are expressed as memory profiles.
• State Hub: For tracking this as the direct follow-on to CYA-WP-0002.

Activation & Ralph Execution

Status: active — activated for ralph-workplan loop execution (HEUREKA promise). This workplan directly continues the memory journey from CYA-WP-0002, moving from basic real memory to proactive, contextually activated memory with built-in retrospection for continuous user-driven optimization.

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Status note: Picks up directly where CYA-WP-0002 left off.