diff --git a/src/cliproxy/executor/index.ts b/src/cliproxy/executor/index.ts
index 2f534ff2..b8dbcb7a 100644
--- a/src/cliproxy/executor/index.ts
+++ b/src/cliproxy/executor/index.ts
@@ -572,7 +572,7 @@ export async function execClaudeWithCLIProxy(
       console.error('    Alias: --thinking xhigh (same behavior)');
     } else {
       console.error('    Examples: --thinking low, --thinking 8192, --thinking off');
-      console.error('    Levels: minimal, low, medium, high, xhigh, auto');
+      console.error('    Levels: minimal, low, medium, high, xhigh, max, auto');
     }
 
     process.exit(1);
diff --git a/src/commands/config-thinking-command.ts b/src/commands/config-thinking-command.ts
index 36b55b41..646d4571 100644
--- a/src/commands/config-thinking-command.ts
+++ b/src/commands/config-thinking-command.ts
@@ -60,7 +60,7 @@ function showHelp(): void {
 
   console.log(subheader('Levels:'));
   console.log(
-    `  ${dim('minimal (512), low (1K), medium (8K), high (24K), xhigh (32K), auto, off')}`
+    `  ${dim('minimal (512), low (1K), medium (8K), high (24K), xhigh (32K), max (adaptive ceiling), auto, off')}`
   );
   console.log('');
 
diff --git a/src/config/unified-config-loader.ts b/src/config/unified-config-loader.ts
index a3548fc6..f18e39bc 100644
--- a/src/config/unified-config-loader.ts
+++ b/src/config/unified-config-loader.ts
@@ -904,7 +904,9 @@ function generateYamlWithComments(config: UnifiedConfig): string {
     lines.push(
       '# Modes: auto (use tier_defaults), off (disable), manual (--thinking/--effort flags)'
     );
-    lines.push('# Levels: minimal (512), low (1K), medium (8K), high (24K), xhigh (32K), auto');
+    lines.push(
+      '# Levels: minimal (512), low (1K), medium (8K), high (24K), xhigh (32K), max (adaptive ceiling), auto'
+    );
     lines.push('# Override: Set global override value (number or level name)');
     lines.push('# Provider overrides: Per-provider tier defaults');
     lines.push('# ----------------------------------------------------------------------------');
diff --git a/tests/unit/commands/config-thinking-command.test.ts b/tests/unit/commands/config-thinking-command.test.ts
index e98efedb..3c9f7f4e 100644
--- a/tests/unit/commands/config-thinking-command.test.ts
+++ b/tests/unit/commands/config-thinking-command.test.ts
@@ -35,6 +35,7 @@ describe('config thinking override normalization', () => {
 
   it('accepts valid levels', () => {
     expect(parseThinkingOverrideInput('High')).toEqual({ value: 'high' });
+    expect(parseThinkingOverrideInput('Max')).toEqual({ value: 'max' });
   });
 
   it('validates numeric bounds', () => {
diff --git a/ui/src/pages/settings/sections/thinking/index.tsx b/ui/src/pages/settings/sections/thinking/index.tsx
index d4c57e74..1fd52591 100644
--- a/ui/src/pages/settings/sections/thinking/index.tsx
+++ b/ui/src/pages/settings/sections/thinking/index.tsx
@@ -32,6 +32,7 @@ const THINKING_LEVELS = [
   { value: 'medium', label: 'Medium (8K tokens)' },
   { value: 'high', label: 'High (24K tokens)' },
   { value: 'xhigh', label: 'Extra High (32K tokens)' },
+  { value: 'max', label: 'Max (adaptive ceiling)' },
   { value: 'auto', label: 'Auto (dynamic)' },
 ];