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+---
+id: CYA-WP-0003
+type: workplan
+title: "Contextual Memory Activation and Retrospection Loops for Continuous Optimization"
+domain: capabilities
+repo: can-you-assist
+status: proposed
+owner: grok
+topic_slug: foerster-capabilities
+created: "2026-05-27"
+updated: "2026-05-27"
+state_hub_workstream_id: null
+---
+
+# 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
+
+```task
+id: CYA-WP-0003-T01
+status: todo
+priority: high
+state_hub_task_id: null
+```
+
+- Deeply align the two ideas (directory-bound activation + regular retrospections) with INTENT.md and MemoryVision.md.
+- Define clear models for:
+  - "Memory activation" (what gets recalled automatically, when, and why).
+  - Retrospection as a first-class interaction pattern (what is captured, how goals/preferences are updated).
+- Produce a short design note (or section in MemoryVision) describing the interaction loop.
+- Identify minimal extensions needed to the existing memory ports and data model.
+
+**Acceptance criteria**:
+- Clear, written concept exists and is consistent with INTENT and MemoryVision.
+- The two ideas are shown to reinforce each other rather than compete.
+
+### T02 — Extend memory ports and data model for activation and retrospection
+
+```task
+id: CYA-WP-0003-T02
+status: todo
+priority: high
+state_hub_task_id: null
+```
+
+- 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
+
+```task
+id: CYA-WP-0003-T03
+status: todo
+priority: high
+state_hub_task_id: null
+```
+
+- 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
+
+```task
+id: CYA-WP-0003-T04
+status: todo
+priority: high
+state_hub_task_id: null
+```
+
+- 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
+
+```task
+id: CYA-WP-0003-T05
+status: todo
+priority: medium
+state_hub_task_id: null
+```
+
+- 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
+
+```task
+id: CYA-WP-0003-T06
+status: todo
+priority: high
+state_hub_task_id: null
+```
+
+- 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
+
+```task
+id: CYA-WP-0003-T07
+status: todo
+priority: medium
+state_hub_task_id: null
+```
+
+- 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.
+
+## Proposed Status & Activation
+
+This workplan is created in `proposed` status. It should be reviewed, moved to `ready`, and activated once the team confirms alignment with phase-memory's current and near-term capabilities.
+
+---
+
+**Status note**: This workplan picks up directly where CYA-WP-0002 left off, moving from "we now have real memory" to "memory is actively and intelligently helping the user in context, with a built-in mechanism for continuous improvement."
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