diff --git a/documentation/ROADMAP.md b/documentation/ROADMAP.md
index af3fc2c..8df7103 100644
--- a/documentation/ROADMAP.md
+++ b/documentation/ROADMAP.md
@@ -78,3 +78,4 @@
 - **Multi-host local models** — per-user config already supports multiple hosts; routing logic TBD
 - **WhatsApp** — requires Business API account or a bridge; not started
 - **Docling** (https://github.com/docling-project/docling) — IBM Research doc parser; converts PDF/DOCX/PPTX/images → clean Markdown/JSON for LLM ingestion; would enhance file attachments and the knowledge import pipeline
+- **Session checkpoint compaction ("janitor" role)** — cheap/fast model summarizes stale session prefix on a turn/token threshold; keeps expensive model context lean; design in `TODO__Agents.md`
diff --git a/documentation/TODO__Agents.md b/documentation/TODO__Agents.md
index 97b6a5f..fbad3d0 100644
--- a/documentation/TODO__Agents.md
+++ b/documentation/TODO__Agents.md
@@ -211,6 +211,44 @@ Upload an image or document inline and have it flow into context.
 - [x] Text/code files read as UTF-8, injected as fenced code block in message
 - [x] Thumbnail/filename shown above sent message in UI
 
+### [Intelligence] Session checkpoint compaction — "janitor" role
+Proactive in-session context pruning using a cheap/fast model to keep expensive
+model costs down as sessions grow. Not continuous per-token — checkpoint-triggered.
+
+**Design:**
+- New `janitor` role in the model registry (alongside `chat`, `orchestrator`, `distill`)
+  - Assign a cheap/fast model: Haiku 4.5, local Gemma E4B, or similar
+  - Falls back to the `distill` role model if `janitor` is not configured
+- Trigger condition (either/or): session exceeds N turns (e.g. 20) OR estimated token
+  count exceeds a threshold (e.g. 12K tokens of history)
+- On trigger: call janitor model with the oldest half of session history; ask it to
+  write a compact "what we've established so far" summary block (3–8 sentences)
+- Replace the compacted turns with a single synthetic `assistant` message:
+  `[Session checkpoint — {N} turns summarized]: {summary}`
+- The remaining recent turns stay untouched — only the stale prefix is replaced
+- Token estimate: count chars / 4 as a cheap heuristic; no exact tokenizer needed
+
+**Files to change:**
+- `model_registry.py` — add `janitor` to `ROLE_DEFAULT_TOOLS` (empty list — no tools)
+  and to the roles UI in `settings/models`
+- `session_store.py` — add `maybe_checkpoint(session_id)` that checks turn count /
+  estimated tokens and calls the janitor model if threshold is exceeded
+- `openai_orchestrator.py` — call `maybe_checkpoint()` at the start of each run,
+  before building the active tool list and context
+- `orchestrator_engine.py` — same, before building the Gemini context
+- Settings UI — expose janitor turn/token thresholds as configurable values
+  (default: 20 turns or 12K history tokens)
+
+**Economics:**
+- Haiku 4.5: ~$0.80/1M input — compacting 10K tokens costs ~$0.008
+- Saves 8–12K tokens on every subsequent Sonnet/Opus call in that session
+- Break-even after 1–2 expensive model calls post-checkpoint
+- Local janitor (Gemma E4B) = effectively free; ideal default when available
+
+**Not needed yet** — most sessions are short enough that existing `_compact_messages()`
+heuristic handles the worst cases. Priority rises with dev-agent pipeline work where
+aider tool results can be very large.
+
 ### [Auth] Encrypted sessions
 Allow users to opt-in to per-session encryption so session logs on disk cannot be
 read without the user's key.