mom: add context usage to thread summary, update docs

- Usage summary now shows context tokens vs model context window
- Updated CHANGELOG.md with all recent changes
- Updated README.md with new file structure (log.jsonl/context.jsonl)

packages/mom/CHANGELOG.md

@@ -2,6 +2,31 @@
 
 ## [Unreleased]
 
+### Changed
+
+- Complete rewrite of message handling architecture
+  - `log.jsonl` is now the source of truth for all channel messages
+  - `context.jsonl` stores LLM context (messages sent to Claude)
+  - Sync mechanism ensures context.jsonl stays in sync with log.jsonl at run start
+  - Session header written immediately on new session creation (not lazily)
+
+- Backfill improvements
+  - Only backfills channels that already have a `log.jsonl` file
+  - Strips @mentions from backfilled messages (consistent with live messages)
+  - Uses largest timestamp in log for efficient incremental backfill
+  - Fetches DM channels in addition to public/private channels
+
+- Message handling improvements
+  - Channel chatter (messages without @mention) logged but doesn't trigger processing
+  - Messages sent while mom is busy are logged and synced on next run
+  - Pre-startup messages (replayed by Slack on reconnect) logged but not auto-processed
+  - Stop command executes immediately (not queued), can interrupt running tasks
+  - Channel @mentions no longer double-logged (was firing both app_mention and message events)
+
+- Usage summary now includes context window usage
+  - Shows current context tokens vs model's context window
+  - Example: `Context: 4.2k / 200k (2.1%)`
+
 ### Fixed
 
 - Slack API errors (msg_too_long) no longer crash the process
@@ -13,20 +38,12 @@
 - Private channel messages not being logged
   - Added `message.groups` to required bot events in README
   - Added `groups:history` and `groups:read` to required scopes in README
-  - `app_mention` handler now logs messages directly instead of relying on `message` event
+
-  - Added deduplication in `ChannelStore.logMessage()` to prevent double-logging
+- Stop command now updates "Stopping..." to "Stopped" instead of posting two messages
 
 ### Added
 
 - Port truncation logic from coding-agent: bash and read tools now use consistent 2000 lines OR 50KB limits with actionable notices
-- Remove redundant context history truncation (tools already provide truncation with actionable hints)
-
-- Message backfill on startup (#103)
-  - Fetches missed messages from Slack using `conversations.history` API when mom restarts
-  - Backfills up to 3 pages (3000 messages) per channel since last logged timestamp
-  - Includes mom's own responses and user messages (excludes other bots)
-  - Downloads attachments from backfilled messages
-  - Logs progress: channel count, per-channel message counts, total with duration
 
 ## [0.10.2] - 2025-11-27
 

packages/mom/README.md

@@ -145,24 +145,27 @@ You provide mom with a **data directory** (e.g., `./data`) as her workspace. Whi
 ```
 ./data/                         # Your host directory
   ├── MEMORY.md                 # Global memory (shared across channels)
+  ├── settings.json             # Global settings (compaction, retry, etc.)
   ├── skills/                   # Global custom CLI tools mom creates
   ├── C123ABC/                  # Each Slack channel gets a directory
   │   ├── MEMORY.md             # Channel-specific memory
-  │   ├── log.jsonl             # Full conversation history
+  │   ├── log.jsonl             # Full message history (source of truth)
+  │   ├── context.jsonl         # LLM context (synced from log.jsonl)
   │   ├── attachments/          # Files users shared
   │   ├── scratch/              # Mom's working directory
   │   └── skills/               # Channel-specific CLI tools
-  └── C456DEF/                  # Another channel
+  └── D456DEF/                  # DM channels also get directories
       └── ...
 ```
 
 **What's stored here:**
-- Conversation logs and Slack attachments. These are automatically stored by mom
+- `log.jsonl`: All channel messages (user messages, bot responses). Source of truth.
-- Memory files. Context mom remembers across sessions
+- `context.jsonl`: Messages sent to Claude. Synced from log.jsonl at each run start.
+- Memory files: Context mom remembers across sessions
 - Custom tools/scripts mom creates (aka "skills")
 - Working files, cloned repos, generated output
 
-This is also where mom efficiently greps channel log files for conversation history, giving her essentially infinite context.
+Mom efficiently greps `log.jsonl` for conversation history, giving her essentially infinite context beyond what's in `context.jsonl`.
 
 ### Memory
 
@@ -230,33 +233,41 @@ Mom will read the `SKILL.md` file before using a skill, and reuse stored credent
 
 Update mom anytime with `npm install -g @mariozechner/pi-mom`. This only updates the Node.js app on your host. Anything mom installed inside the Docker container remains unchanged.
 
-## Message History (log.jsonl)
+## Message History
 
-Each channel's `log.jsonl` contains the full conversation history. Every message, tool call, and result. Format: one JSON object per line with ISO 8601 timestamps:
+Mom uses two files per channel to manage messages:
+
+### log.jsonl (Source of Truth)
+
+All channel messages are stored here. This includes user messages, channel chatter (messages without @mention), and bot responses. Format: one JSON object per line with ISO 8601 timestamps:
 
 ```typescript
 interface LoggedMessage {
   date: string;        // ISO 8601 (e.g., "2025-11-26T10:44:00.000Z")
-  ts: string;          // Slack timestamp or epoch ms
+  ts: string;          // Slack timestamp (seconds.microseconds)
   user: string;        // User ID or "bot"
   userName?: string;   // Handle (e.g., "mario")
   displayName?: string; // Display name (e.g., "Mario Zechner")
-  text: string;        // Message text
+  text: string;        // Message text (@mentions stripped)
-  attachments: Array<{
+  attachments: string[]; // Filenames of attachments
-    original: string;  // Original filename
-    local: string;     // Path relative to data dir
-  }>;
   isBot: boolean;
 }
 ```
 
 **Example:**
 ```json
-{"date":"2025-11-26T10:44:00.123Z","ts":"1732619040.123456","user":"U123ABC","userName":"mario","text":"@mom hello","attachments":[],"isBot":false}
+{"date":"2025-11-26T10:44:00.123Z","ts":"1732619040.123456","user":"U123ABC","userName":"mario","text":"hello","attachments":[],"isBot":false}
 {"date":"2025-11-26T10:44:05.456Z","ts":"1732619045456","user":"bot","text":"Hi! How can I help?","attachments":[],"isBot":true}
 ```
 
-Mom knows how to query these logs efficiently (see [her system prompt](src/agent.ts)) to avoid context overflow when searching conversation history.
+### context.jsonl (LLM Context)
+
+Messages sent to Claude are stored here. This is synced from `log.jsonl` at the start of each run to ensure:
+- Backfilled messages (from Slack API on startup) are included
+- Channel chatter between @mentions is included
+- Messages sent while mom was busy are included
+
+Mom knows how to query `log.jsonl` efficiently (see [her system prompt](src/agent.ts)) for older history beyond what's in context.
 
 ## Security Considerations
 
@@ -339,9 +350,10 @@ mom --sandbox=docker:mom-exec ./data-exec
 
 ### Code Structure
 
-- `src/main.ts`: Entry point, CLI arg parsing, message routing
+- `src/main.ts`: Entry point, CLI arg parsing, handler setup, SlackContext adapter
-- `src/agent.ts`: Agent runner, event handling, tool execution
+- `src/agent.ts`: Agent runner, event handling, tool execution, session management
-- `src/slack.ts`: Slack integration, context management, message posting
+- `src/slack.ts`: Slack integration (Socket Mode), backfill, message logging
+- `src/context.ts`: Session manager (context.jsonl), log-to-context sync
 - `src/store.ts`: Channel data persistence, attachment downloads
 - `src/log.ts`: Centralized logging (console output)
 - `src/sandbox.ts`: Docker/host sandbox execution

packages/mom/src/agent.ts

@@ -617,9 +617,24 @@ function createRunner(sandboxConfig: SandboxConfig, channelId: string, channelDi
 				}
 			}
 
-			// Log usage summary
+			// Log usage summary with context info
 			if (runState.totalUsage.cost.total > 0) {
-				const summary = log.logUsageSummary(runState.logCtx!, runState.totalUsage);
+				// Get last non-aborted assistant message for context calculation
+				const messages = session.messages;
+				const lastAssistantMessage = messages
+					.slice()
+					.reverse()
+					.find((m) => m.role === "assistant" && (m as any).stopReason !== "aborted") as any;
+
+				const contextTokens = lastAssistantMessage
+					? lastAssistantMessage.usage.input +
+						lastAssistantMessage.usage.output +
+						lastAssistantMessage.usage.cacheRead +
+						lastAssistantMessage.usage.cacheWrite
+					: 0;
+				const contextWindow = model.contextWindow || 200000;
+
+				const summary = log.logUsageSummary(runState.logCtx!, runState.totalUsage, contextTokens, contextWindow);
 				runState.queue.enqueue(() => ctx.respondInThread(summary), "usage summary");
 				await queueChain;
 			}

packages/mom/src/log.ts

@@ -195,13 +195,26 @@ export function logUsageSummary(
 		cacheWrite: number;
 		cost: { input: number; output: number; cacheRead: number; cacheWrite: number; total: number };
 	},
+	contextTokens?: number,
+	contextWindow?: number,
 ): string {
+	const formatTokens = (count: number): string => {
+		if (count < 1000) return count.toString();
+		if (count < 10000) return (count / 1000).toFixed(1) + "k";
+		if (count < 1000000) return Math.round(count / 1000) + "k";
+		return (count / 1000000).toFixed(1) + "M";
+	};
+
 	const lines: string[] = [];
 	lines.push("*Usage Summary*");
 	lines.push(`Tokens: ${usage.input.toLocaleString()} in, ${usage.output.toLocaleString()} out`);
 	if (usage.cacheRead > 0 || usage.cacheWrite > 0) {
 		lines.push(`Cache: ${usage.cacheRead.toLocaleString()} read, ${usage.cacheWrite.toLocaleString()} write`);
 	}
+	if (contextTokens && contextWindow) {
+		const contextPercent = ((contextTokens / contextWindow) * 100).toFixed(1);
+		lines.push(`Context: ${formatTokens(contextTokens)} / ${formatTokens(contextWindow)} (${contextPercent}%)`);
+	}
 	lines.push(
 		`Cost: $${usage.cost.input.toFixed(4)} in, $${usage.cost.output.toFixed(4)} out` +
 			(usage.cacheRead > 0 || usage.cacheWrite > 0