feat(commands,audit): add /context command and proactive compaction audit events

docs/plans/state.json

@@ -1,6 +1,6 @@
 {
   "version": "1.0",
-  "updated_at": "2026-02-16",
+  "updated_at": "2026-02-17",
   "description": "Tracks the status of all Flynn plans and implementation phases",
   "plans": {
     "automation-daily-briefing-and-cron-backup-scheduling": {
@@ -3504,8 +3504,8 @@
     "proactive-context-usage-and-compaction-signals": {
       "status": "completed",
       "date": "2026-02-16",
-      "updated": "2026-02-16",
+      "updated": "2026-02-17",
-      "summary": "Implemented proactive context-window management end-to-end: orchestrator now exposes estimated context budget, emits staged context alerts, writes checkpoint summaries to memory near threshold, and can auto-compact proactively. Gateway now emits `context_warning` stream events during `agent.send`, serves `system.contextUsage` snapshots, and dashboard usage UI includes context budget visibility. Added config schema support under `compaction.proactive`, mapped runtime wiring in both WS SessionBridge and channel routing paths, and updated protocol/docs/default config examples with focused tests.",
+      "summary": "Implemented proactive context-window management end-to-end: orchestrator now exposes estimated context budget, emits staged context alerts, writes checkpoint summaries to memory near threshold, and can auto-compact proactively. Gateway now emits `context_warning` stream events during `agent.send`, serves `system.contextUsage` snapshots, and dashboard usage UI includes context budget visibility. Added config schema support under `compaction.proactive`, mapped runtime wiring in both WS SessionBridge and channel routing paths, and updated protocol/docs/default config examples with focused tests. Follow-up added `/context` command fast-path visibility and dedicated audit events for proactive checkpoint writes and proactive auto-compaction.",
       "files_modified": [
         "src/context/compaction.ts",
         "src/backends/native/prompts.ts",
@@ -3525,13 +3525,19 @@
         "src/daemon/services.ts",
         "src/gateway/ui/pages/chat.js",
         "src/gateway/ui/pages/usage.js",
+        "src/commands/builtin/index.ts",
+        "src/commands/types.ts",
+        "src/commands/index.ts",
+        "src/commands/builtin/index.test.ts",
+        "src/audit/types.ts",
+        "src/audit/logger.ts",
         "docs/api/PROTOCOL.md",
         "README.md",
         "docs/performance/TUNING.md",
         "config/default.yaml",
         "docs/plans/state.json"
       ],
-      "test_status": "pnpm test:run src/backends/native/orchestrator.test.ts src/config/schema.test.ts src/gateway/handlers/agent.test.ts src/gateway/handlers/handlers.test.ts src/gateway/protocol.test.ts + pnpm typecheck passing"
+      "test_status": "pnpm test:run src/backends/native/orchestrator.test.ts src/config/schema.test.ts src/gateway/handlers/agent.test.ts src/gateway/handlers/handlers.test.ts src/gateway/protocol.test.ts src/commands/builtin/index.test.ts + pnpm typecheck passing"
     }
   },
   "overall_progress": {

src/audit/logger.ts

@@ -16,6 +16,8 @@ import type {
   SessionMessageEvent,
   SessionDeleteEvent,
   SessionCompactEvent,
+  SessionCheckpointEvent,
+  SessionAutoCompactEvent,
   UserActionEvent,
   CronTriggerEvent,
   WebhookReceiveEvent,
@@ -175,6 +177,16 @@ export class AuditLogger {
     this.write({ level: 'debug', event_type: 'session.compact', event: event as unknown as Record<string, unknown> });
   }
 
+  sessionCheckpoint(event: SessionCheckpointEvent): void {
+    if (!this.shouldLog('sessions', 'debug')) {return;}
+    this.write({ level: 'debug', event_type: 'session.checkpoint', event: event as unknown as Record<string, unknown> });
+  }
+
+  sessionAutoCompact(event: SessionAutoCompactEvent): void {
+    if (!this.shouldLog('sessions', 'debug')) {return;}
+    this.write({ level: 'debug', event_type: 'session.auto_compact', event: event as unknown as Record<string, unknown> });
+  }
+
   userAction(event: UserActionEvent): void {
     if (!this.shouldLog('sessions', 'info')) {return;}
     this.write({ level: 'info', event_type: 'user.action', event: event as unknown as Record<string, unknown> });

src/audit/types.ts

@@ -10,7 +10,7 @@ export type AuditEventType =
   // Skills installer
   | 'skills.installer.execution_blocked' | 'skills.installer.command_result' | 'skills.registry_install'
   // Session lifecycle
-  | 'session.create' | 'session.message' | 'session.delete' | 'session.transfer' | 'session.compact' | 'user.action'
+  | 'session.create' | 'session.message' | 'session.delete' | 'session.transfer' | 'session.compact' | 'session.checkpoint' | 'session.auto_compact' | 'user.action'
   // Automation - Cron
   | 'cron.trigger' | 'cron.sent' | 'cron.add' | 'cron.remove'
   // Automation - Webhook
@@ -182,6 +182,22 @@ export interface SessionCompactEvent {
   tokens_after: number;
 }
 
+export interface SessionCheckpointEvent {
+  session_id: string;
+  namespace: string;
+  chars_written: number;
+  usage_pct: number;
+}
+
+export interface SessionAutoCompactEvent {
+  session_id: string;
+  usage_pct_before: number;
+  usage_pct_after: number;
+  compacted: boolean;
+  tokens_before: number;
+  tokens_after: number;
+}
+
 export interface UserActionEvent {
   session_id: string;
   channel: string;

src/backends/native/orchestrator.test.ts

@@ -927,6 +927,10 @@ describe('AgentOrchestrator', () => {
         deleteConfig: vi.fn(),
       };
 
+      const sessionCheckpoint = vi.fn();
+      const previousAuditLogger = auditLogger;
+      initAuditLogger({ sessionCheckpoint } as unknown as AuditLogger);
+
       const orchestrator = new AgentOrchestrator({
         modelRouter: mockRouter,
         systemPrompt: 'You are helpful.',
@@ -958,17 +962,23 @@ describe('AgentOrchestrator', () => {
         },
       });
 
-      await orchestrator.process('ping');
+      try {
-      const alert = orchestrator.consumeContextAlert();
+        await orchestrator.process('ping');
-      expect(alert?.level).toBe('checkpoint');
+        const alert = orchestrator.consumeContextAlert();
-      expect(alert?.actions.checkpointSaved).toBe(true);
+        expect(alert?.level).toBe('checkpoint');
-      expect(alert?.actions.checkpointNamespace).toContain('session/checkpoints');
+        expect(alert?.actions.checkpointSaved).toBe(true);
-      expect(orchestrator.consumeContextAlert()).toBeUndefined();
+        expect(alert?.actions.checkpointNamespace).toContain('session/checkpoints');
+        expect(orchestrator.consumeContextAlert()).toBeUndefined();
 
-      const stored = memoryStore.read('session/checkpoints/ws/context-test');
+        const stored = memoryStore.read('session/checkpoints/ws/context-test');
-      expect(stored.length).toBeGreaterThan(0);
+        expect(stored.length).toBeGreaterThan(0);
-
+        expect(sessionCheckpoint).toHaveBeenCalledWith(expect.objectContaining({
-      rmSync(tempDir, { recursive: true, force: true });
+          session_id: 'ws:context-test',
+        }));
+      } finally {
+        initAuditLogger(previousAuditLogger as unknown as AuditLogger);
+        rmSync(tempDir, { recursive: true, force: true });
+      }
     });
 
     it('auto-compacts proactively at critical threshold and emits alert', async () => {
@@ -1006,6 +1016,11 @@ describe('AgentOrchestrator', () => {
         deleteConfig: vi.fn(),
       };
 
+      const sessionAutoCompact = vi.fn();
+      const sessionCompact = vi.fn();
+      const previousAuditLogger = auditLogger;
+      initAuditLogger({ sessionAutoCompact, sessionCompact } as unknown as AuditLogger);
+
       const orchestrator = new AgentOrchestrator({
         modelRouter: compactRouter,
         systemPrompt: 'You are helpful.',
@@ -1036,10 +1051,18 @@ describe('AgentOrchestrator', () => {
         },
       });
 
-      await orchestrator.process('continue');
+      try {
-      const alert = orchestrator.consumeContextAlert();
+        await orchestrator.process('continue');
-      expect(alert?.actions.autoCompacted).toBe(true);
+        const alert = orchestrator.consumeContextAlert();
-      expect(history.length).toBeLessThan(6);
+        expect(alert?.actions.autoCompacted).toBe(true);
+        expect(history.length).toBeLessThan(6);
+        expect(sessionAutoCompact).toHaveBeenCalledWith(expect.objectContaining({
+          session_id: 'ws:auto-compact',
+          compacted: true,
+        }));
+      } finally {
+        initAuditLogger(previousAuditLogger as unknown as AuditLogger);
+      }
     });
   });
 });

src/backends/native/orchestrator.ts

@@ -573,6 +573,7 @@ export class AgentOrchestrator {
     }
 
     if (level === 'critical') {
+      const beforeAuto = budget;
       try {
         const result = await this.compact();
         autoCompacted = Boolean(result && result.compactedCount > 0);
@@ -580,6 +581,16 @@ export class AgentOrchestrator {
         console.warn('[Flynn:compact] Proactive auto-compaction failed:', error);
       }
       budget = this.getContextBudget();
+      if (this._session) {
+        auditLogger?.sessionAutoCompact({
+          session_id: this._session.id,
+          usage_pct_before: beforeAuto.usagePct,
+          usage_pct_after: budget.usagePct,
+          compacted: autoCompacted,
+          tokens_before: beforeAuto.estimatedTokens,
+          tokens_after: budget.estimatedTokens,
+        });
+      }
       level = this._resolveContextAlertLevel(budget.usagePct);
     }
 
@@ -691,6 +702,12 @@ export class AgentOrchestrator {
       const namespace = `${namespaceBase}/${this._sanitizeSessionId(this._session.id)}`;
       const block = `## ${new Date().toISOString()}\n\n${summary}\n\n`;
       this._memoryStore.write(namespace, block, 'append');
+      auditLogger?.sessionCheckpoint({
+        session_id: this._session.id,
+        namespace,
+        chars_written: block.length,
+        usage_pct: this.getContextBudget().usagePct,
+      });
       this._lastCheckpointAt = Date.now();
       return { saved: true, namespace };
     } catch (error) {

src/commands/builtin/index.test.ts

@@ -1,6 +1,6 @@
 import { describe, it, expect, vi } from 'vitest';
 
-import { createElevateCommand, createModelCommand, createQueueCommand } from './index.js';
+import { createContextCommand, createElevateCommand, createModelCommand, createQueueCommand } from './index.js';
 
 describe('builtin /model command', () => {
   it('passes through the full argument string', async () => {
@@ -111,3 +111,31 @@ describe('builtin /queue command', () => {
     expect(result).toEqual({ handled: true, text: 'reset' });
   });
 });
+
+describe('builtin /context command', () => {
+  it('returns context usage text from services', async () => {
+    const cmd = createContextCommand();
+    const getContext = vi.fn(() => 'Context Usage\n\n75.0%');
+    const result = await cmd.execute([], {
+      channel: 'test',
+      senderId: 'user',
+      sessionId: 's1',
+      rawInput: '/context',
+      services: { getContext },
+    });
+    expect(getContext).toHaveBeenCalledOnce();
+    expect(result).toEqual({ handled: true, text: 'Context Usage\n\n75.0%' });
+  });
+
+  it('returns not-available when service is missing', async () => {
+    const cmd = createContextCommand();
+    const result = await cmd.execute([], {
+      channel: 'test',
+      senderId: 'user',
+      sessionId: 's1',
+      rawInput: '/context',
+      services: {},
+    });
+    expect(result).toEqual({ handled: true, text: 'Context command is not available in this session.' });
+  });
+});

src/commands/builtin/index.ts

@@ -65,6 +65,22 @@ export function createUsageCommand(): CommandDefinition {
   };
 }
 
+export function createContextCommand(): CommandDefinition {
+  return {
+    name: 'context',
+    description: 'Show context window usage',
+    execute: async (_args, ctx) => {
+      if (!ctx.services?.getContext) {
+        return notAvailable('Context command');
+      }
+      return {
+        handled: true,
+        text: await ctx.services.getContext(),
+      };
+    },
+  };
+}
+
 export function createModelCommand(): CommandDefinition {
   return {
     name: 'model',
@@ -183,6 +199,7 @@ export function registerBuiltinCommands(registry: CommandRegistry): void {
   registry.register(createHelpCommand(registry));
   registry.register(createStatusCommand());
   registry.register(createUsageCommand());
+  registry.register(createContextCommand());
   registry.register(createModelCommand());
   registry.register(createCompactCommand());
   registry.register(createResetCommand());

src/commands/index.ts

@@ -4,6 +4,7 @@ export {
   createHelpCommand,
   createStatusCommand,
   createUsageCommand,
+  createContextCommand,
   createModelCommand,
   createCompactCommand,
   createResetCommand,

src/commands/types.ts

@@ -21,6 +21,7 @@ export interface CommandDefinition {
 export interface CommandServices {
   getStatus?: () => Promise<string> | string;
   getUsage?: () => Promise<string> | string;
+  getContext?: () => Promise<string> | string;
   getModel?: () => Promise<string> | string;
   setModel?: (tier: string) => Promise<string> | string;
   compact?: () => Promise<string> | string;

src/gateway/handlers/agent.test.ts

@@ -82,6 +82,25 @@ describe('createAgentHandlers command fast-path', () => {
     expect((event.data as { content: string }).content).toContain('Token Usage');
   });
 
+  it('handles /context command via fast-path', async () => {
+    const sent: OutboundMessage[] = [];
+    const send = vi.fn((msg: OutboundMessage) => sent.push(msg));
+    const req: GatewayRequest = {
+      id: 8,
+      method: 'agent.send',
+      params: { message: '/context', connectionId: 'conn-1' },
+    };
+
+    await handlers['agent.send'](req, send);
+
+    expect(mockAgent.process).not.toHaveBeenCalled();
+    expect(sent).toHaveLength(1);
+    const event = sent[0] as GatewayEvent;
+    expect(event.event).toBe('done');
+    expect((event.data as { content: string }).content).toContain('Context Usage');
+    expect((event.data as { content: string }).content).toContain('Compaction threshold');
+  });
+
   it('handles metadata commands via fast-path', async () => {
     const sent: OutboundMessage[] = [];
     const send = vi.fn((msg: OutboundMessage) => sent.push(msg));

src/gateway/handlers/agent.ts

@@ -126,6 +126,19 @@ export function createAgentHandlers(deps: AgentHandlerDeps) {
 
                   return lines.join('\n');
                 },
+                getContext: () => {
+                  const budget = agent.getContextBudget();
+                  const lines = [
+                    '**Context Usage**',
+                    '',
+                    `Estimated: ${budget.estimatedTokens.toLocaleString()} / ${budget.contextWindow.toLocaleString()} tokens`,
+                    `Remaining: ${budget.remainingTokens.toLocaleString()} tokens`,
+                    `Usage: ${budget.usagePct.toFixed(1)}%`,
+                    `Compaction threshold: ${budget.thresholdPct}% (${budget.thresholdTokens.toLocaleString()} tokens)`,
+                    `Should compact: ${budget.shouldCompact ? 'yes' : 'no'}`,
+                  ];
+                  return lines.join('\n');
+                },
                 getModel: () => `Current model tier: ${agent.getModelTier()}`,
                 setModel: (input) => {
                   const raw = input.trim();