diff --git a/README.md b/README.md
index 7eff0e2..2704a29 100644
--- a/README.md
+++ b/README.md
@@ -1024,6 +1024,11 @@ sessions:
 
 Flynn writes structured audit events to `audit.path`, including tool execution, session lifecycle, and user actions (`user.action`) from both channel and gateway requests.
 
+Session lifecycle now includes proactive context maintenance events:
+- `session.compact` for normal compaction passes
+- `session.checkpoint` when proactive checkpoint summaries are written to memory
+- `session.auto_compact` when proactive critical-threshold auto-compaction runs
+
 ## Gateway Lock
 
 Single-client mode for the WebSocket gateway. When enabled, only one WebSocket connection is allowed at a time. Additional connections are rejected with close code `4003`.
diff --git a/docs/operations/OPERATOR_PACK.md b/docs/operations/OPERATOR_PACK.md
index 3461542..ff50477 100644
--- a/docs/operations/OPERATOR_PACK.md
+++ b/docs/operations/OPERATOR_PACK.md
@@ -70,3 +70,4 @@ automation:
 - Heartbeat notification noise is controlled by `automation.heartbeat.notify_cooldown` (default `30m`).
 - If `notify_cooldown` is invalid, Flynn falls back to `30m` and logs a warning.
 - Re-running setup Automation detects an existing Operator Pack and asks whether to reconfigure.
+- For context-pressure observability, monitor audit events `session.checkpoint` and `session.auto_compact`.
diff --git a/docs/plans/state.json b/docs/plans/state.json
index be6f909..e89ee21 100644
--- a/docs/plans/state.json
+++ b/docs/plans/state.json
@@ -3505,7 +3505,7 @@
       "status": "completed",
       "date": "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. Follow-up added `/context` command fast-path visibility and dedicated audit events for proactive checkpoint writes and proactive auto-compaction.",
+      "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, TUI parser/help/autocomplete + handler parity for `/context`, dedicated audit events for proactive checkpoint writes and proactive auto-compaction, and operator/docs references for those events.",
       "files_modified": [
         "src/context/compaction.ts",
         "src/backends/native/prompts.ts",
@@ -3525,6 +3525,11 @@
         "src/daemon/services.ts",
         "src/gateway/ui/pages/chat.js",
         "src/gateway/ui/pages/usage.js",
+        "src/gateway/ui/pages/dashboard.js",
+        "src/frontends/tui/commands.ts",
+        "src/frontends/tui/commands.test.ts",
+        "src/frontends/tui/minimal.ts",
+        "src/frontends/tui/components/App.tsx",
         "src/commands/builtin/index.ts",
         "src/commands/types.ts",
         "src/commands/index.ts",
@@ -3533,11 +3538,12 @@
         "src/audit/logger.ts",
         "docs/api/PROTOCOL.md",
         "README.md",
+        "docs/operations/OPERATOR_PACK.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 src/commands/builtin/index.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 src/frontends/tui/commands.test.ts + pnpm typecheck passing"
     }
   },
   "overall_progress": {
diff --git a/src/frontends/tui/commands.test.ts b/src/frontends/tui/commands.test.ts
index 44039c3..81314a0 100644
--- a/src/frontends/tui/commands.test.ts
+++ b/src/frontends/tui/commands.test.ts
@@ -35,6 +35,10 @@ describe('parseCommand', () => {
     expect(parseCommand('/usage')).toEqual({ type: 'usage' });
   });
 
+  it('parses /context command', () => {
+    expect(parseCommand('/context')).toEqual({ type: 'context' });
+  });
+
   it('parses /verbose command', () => {
     expect(parseCommand('/verbose')).toEqual({ type: 'verbose' });
   });
@@ -117,6 +121,7 @@ describe('getHelpText', () => {
     expect(help).toContain('/reset');
     expect(help).toContain('/compact');
     expect(help).toContain('/usage');
+    expect(help).toContain('/context');
     expect(help).toContain('/verbose');
     expect(help).toContain('/queue');
     expect(help).toContain('/elevate');
diff --git a/src/frontends/tui/commands.ts b/src/frontends/tui/commands.ts
index 597feff..09e6ade 100644
--- a/src/frontends/tui/commands.ts
+++ b/src/frontends/tui/commands.ts
@@ -6,6 +6,7 @@ export type Command =
   | { type: 'fullscreen' }
   | { type: 'compact' }
   | { type: 'usage' }
+  | { type: 'context' }
   | { type: 'verbose' }
   | { type: 'model'; name?: string; providerModel?: string }
   | { type: 'backend'; provider?: string }
@@ -55,6 +56,11 @@ export function parseCommand(input: string): Command | null {
     return { type: 'usage' };
   }
 
+  // Context
+  if (trimmed === '/context') {
+    return { type: 'context' };
+  }
+
   // Verbose
   if (trimmed === '/verbose') {
     return { type: 'verbose' };
@@ -162,6 +168,7 @@ Commands:
   /reset, /clear, /new   Clear conversation history
   /compact               Compact conversation history
   /usage                 Show token usage and estimated cost
+  /context               Show estimated context-window usage
   /verbose               Toggle verbose mode (show raw streaming and tool output)
   /status                Show session info and token usage
   /fullscreen, /fs       Switch to fullscreen mode
@@ -184,6 +191,7 @@ export const SLASH_COMMANDS = [
   '/new',
   '/compact',
   '/usage',
+  '/context',
   '/verbose',
   '/status',
   '/fullscreen',
@@ -207,6 +215,7 @@ export const COMMAND_TOOLTIPS: Record<string, string> = {
   '/new': 'Start a new conversation',
   '/compact': 'Compact conversation history to save context space',
   '/usage': 'Show token usage and estimated cost',
+  '/context': 'Show estimated context-window usage',
   '/verbose': 'Toggle verbose mode (show raw streaming and tool output)',
   '/status': 'Show session info and token usage',
   '/fullscreen': 'Switch to fullscreen mode',
diff --git a/src/frontends/tui/components/App.tsx b/src/frontends/tui/components/App.tsx
index a64e7f9..e61cbdd 100644
--- a/src/frontends/tui/components/App.tsx
+++ b/src/frontends/tui/components/App.tsx
@@ -12,6 +12,7 @@ import type { HookEngine, HookResult } from '../../../hooks/index.js';
 import type { ModelConfig, ModelProvider } from '../../../config/schema.js';
 import { MODEL_PROVIDERS } from '../../../config/schema.js';
 import { createClientFromConfig } from '../../../daemon/index.js';
+import { estimateMessageTokens, getContextWindow } from '../../../context/tokens.js';
 
 /** Format a tool name like "gmail.list" -> "Gmail: List" */
 function formatToolName(name: string): string {
@@ -239,6 +240,29 @@ export function App({
         return;
       }
 
+      case 'context': {
+        const history = session.getHistory();
+        const estimated = estimateMessageTokens(history);
+        const tier = modelRouter?.getTier() ?? 'default';
+        const modelName = modelRouter?.getLabel(tier) ?? model;
+        const window = getContextWindow(modelName);
+        const usagePct = window > 0 ? (estimated / window) * 100 : 0;
+        const thresholdPct = 80;
+        const thresholdTokens = Math.floor((thresholdPct / 100) * window);
+        const remaining = Math.max(0, window - estimated);
+        const text = [
+          'Context Usage (estimated)',
+          '',
+          `Model: ${modelName}`,
+          `Used: ${estimated.toLocaleString()} / ${window.toLocaleString()} tokens (${usagePct.toFixed(1)}%)`,
+          `Remaining: ${remaining.toLocaleString()} tokens`,
+          `Compaction threshold: ${thresholdPct}% (${thresholdTokens.toLocaleString()} tokens)`,
+          `Should compact: ${estimated > thresholdTokens ? 'yes' : 'no'}`,
+        ].join('\n');
+        setMessages(prev => [...prev, session.addMessage({ role: 'assistant', content: text })]);
+        return;
+      }
+
       case 'verbose': {
         const next = !verbose;
         setVerbose(next);
diff --git a/src/frontends/tui/minimal.ts b/src/frontends/tui/minimal.ts
index b6c14f8..8afafbe 100644
--- a/src/frontends/tui/minimal.ts
+++ b/src/frontends/tui/minimal.ts
@@ -25,6 +25,7 @@ import {
 import type { PairingManager } from '../../channels/pairing.js';
 import { getColoredBanner } from './banner.js';
 import type { HookEngine } from '../../hooks/index.js';
+import { estimateMessageTokens, getContextWindow } from '../../context/tokens.js';
 
 export { parseCommand, type Command };
 
@@ -331,6 +332,10 @@ export class MinimalTui {
         this.handleUsageCommand();
         break;
 
+      case 'context':
+        this.handleContextCommand();
+        break;
+
       case 'verbose':
         this.handleVerboseCommand();
         break;
@@ -382,6 +387,25 @@ export class MinimalTui {
     this.printStatus();
   }
 
+  private handleContextCommand(): void {
+    const history = this.config.session.getHistory();
+    const estimated = estimateMessageTokens(history);
+    const tier = this.config.modelRouter?.getTier() ?? 'default';
+    const modelName = this.config.modelRouter?.getLabel(tier) ?? 'unknown';
+    const window = getContextWindow(modelName);
+    const usagePct = window > 0 ? (estimated / window) * 100 : 0;
+    const thresholdPct = 80;
+    const thresholdTokens = Math.floor((thresholdPct / 100) * window);
+    const remaining = Math.max(0, window - estimated);
+
+    console.log(`${colors.gray}Context usage (estimated):${colors.reset}`);
+    console.log(`  model: ${modelName}`);
+    console.log(`  used: ${estimated.toLocaleString()} / ${window.toLocaleString()} tokens (${usagePct.toFixed(1)}%)`);
+    console.log(`  remaining: ${remaining.toLocaleString()} tokens`);
+    console.log(`  compaction threshold: ${thresholdPct}% (${thresholdTokens.toLocaleString()} tokens)`);
+    console.log(`  should compact: ${estimated > thresholdTokens ? 'yes' : 'no'}\n`);
+  }
+
   private handleVerboseCommand(): void {
     this.verbose = !this.verbose;
     console.log(`${colors.gray}Verbose mode:${colors.reset} ${this.verbose ? 'on' : 'off'}\n`);
diff --git a/src/gateway/ui/pages/dashboard.js b/src/gateway/ui/pages/dashboard.js
index 9d827d9..9991e25 100644
--- a/src/gateway/ui/pages/dashboard.js
+++ b/src/gateway/ui/pages/dashboard.js
@@ -75,6 +75,11 @@ function renderSkeleton(el) {
       <div class="text-muted text-sm">Loading...</div>
     </div>
 
+    <h2 class="section-title">Context Health</h2>
+    <div id="ops-context-health">
+      <div class="text-muted text-sm">Loading...</div>
+    </div>
+
     <h2 class="section-title">Event Stream</h2>
     <div class="event-stream" id="ops-events">
       <div class="event-row event-level-info">Loading events...</div>
@@ -346,6 +351,66 @@ function updateSessionAnalytics(analyticsData) {
   `;
 }
 
+function updateContextHealth(contextData) {
+  const el = document.getElementById('ops-context-health');
+  if (!el) {return;}
+
+  const sessions = contextData?.sessions ?? [];
+  if (sessions.length === 0) {
+    el.innerHTML = '<div class="text-muted text-sm">No active context usage snapshots</div>';
+    return;
+  }
+
+  const sorted = [...sessions].sort((a, b) => (b.budget?.usagePct ?? 0) - (a.budget?.usagePct ?? 0));
+  const top = sorted.slice(0, 8);
+  const highest = top[0]?.budget?.usagePct ?? 0;
+  const overThreshold = sessions.filter(s => (s.budget?.shouldCompact ?? false)).length;
+
+  const summary = `
+    <div class="stats-grid">
+      <div class="stat-card">
+        <div class="stat-label">Highest Usage</div>
+        <div class="stat-value ${highest >= 90 ? 'error' : ''}">${highest.toFixed(1)}%</div>
+      </div>
+      <div class="stat-card">
+        <div class="stat-label">Sessions Near Limit</div>
+        <div class="stat-value ${overThreshold > 0 ? 'error' : ''}">${overThreshold}</div>
+      </div>
+      <div class="stat-card">
+        <div class="stat-label">Active Snapshots</div>
+        <div class="stat-value">${sessions.length}</div>
+      </div>
+    </div>
+  `;
+
+  const rows = top.map((entry) => {
+    const budget = entry.budget ?? {};
+    const usage = budget.usagePct ?? 0;
+    const cls = usage >= 95 ? 'text-error' : usage >= 85 ? 'status-warning' : '';
+    return `<tr>
+      <td>${escapeHtml(entry.sessionId)}</td>
+      <td class="${cls}">${usage.toFixed(1)}%</td>
+      <td>${formatNumber(budget.estimatedTokens ?? 0)} / ${formatNumber(budget.contextWindow ?? 0)}</td>
+      <td>${budget.shouldCompact ? 'yes' : 'no'}</td>
+    </tr>`;
+  }).join('');
+
+  el.innerHTML = `
+    ${summary}
+    <table>
+      <thead>
+        <tr>
+          <th>Session</th>
+          <th>Usage</th>
+          <th>Estimated Tokens</th>
+          <th>Should Compact</th>
+        </tr>
+      </thead>
+      <tbody>${rows}</tbody>
+    </table>
+  `;
+}
+
 function _updateChannels(channelsData) {
   const el = document.getElementById('ops-channels');
   if (!el) {return;}
@@ -414,12 +479,13 @@ async function fetchFast(client) {
 
 async function fetchSlow(client) {
   try {
-    const [health, services, sessionAnalytics] = await Promise.all([
+    const [health, services, sessionAnalytics, contextUsage] = await Promise.all([
       client.call('system.health'),
       client.call('system.services'),
       client.call('system.sessionAnalytics', { days: 14, topLimit: 5 }),
+      client.call('system.contextUsage'),
     ]);
-    return { health, services, sessionAnalytics };
+    return { health, services, sessionAnalytics, contextUsage };
   } catch {
     return null;
   }
@@ -451,6 +517,7 @@ async function loadDashboard(el, client) {
   if (slow) {
     updateServices(slow.services);
     updateSessionAnalytics(slow.sessionAnalytics);
+    updateContextHealth(slow.contextUsage);
   }
 
   // Fast refresh: 3 seconds for metrics, events, requests
@@ -473,6 +540,7 @@ async function loadDashboard(el, client) {
       updateCounters(_lastMetrics, data.health);
       updateServices(data.services);
       updateSessionAnalytics(data.sessionAnalytics);
+      updateContextHealth(data.contextUsage);
     }
   }, 10000);
 }