diff --git a/src/cli/handlers/skillsCli.ts b/src/cli/handlers/skillsCli.ts
index 4d99156ea..74b32059f 100644
--- a/src/cli/handlers/skillsCli.ts
+++ b/src/cli/handlers/skillsCli.ts
@@ -14,6 +14,7 @@ const TRAILING_GLOBAL_BOOLEAN_FLAGS = new Set([
   '--bare',
   '--debug',
   '--debug-to-stderr',
+  '--yolo',
   '--dangerously-skip-permissions',
   '--allow-dangerously-skip-permissions',
   '--disable-slash-commands',
diff --git a/src/entrypoints/cli.test.ts b/src/entrypoints/cli.test.ts
index 60d0997cd..14974985b 100644
--- a/src/entrypoints/cli.test.ts
+++ b/src/entrypoints/cli.test.ts
@@ -565,4 +565,99 @@ describe('Node 24 premature exit regression (issue #1678)', () => {
     expect(src).toMatch(/await main\(\)/)
     expect(src).not.toMatch(/^\s*void main\(\)/m)
   })
+
+  describe('--yolo alias', () => {
+    it('is registered on the main command next to the canonical flag', async () => {
+      const src = await Bun.file(`${import.meta.dir}/../main.tsx`).text()
+      expect(src).toContain(
+        ".option('--yolo, --dangerously-skip-permissions', 'Bypass all permission checks",
+      )
+    })
+
+    it('is registered on the ssh stub command', async () => {
+      const src = await Bun.file(`${import.meta.dir}/../main.tsx`).text()
+      const sshCmd = src.indexOf("program.command('ssh <host> [dir]')")
+      expect(sshCmd).toBeGreaterThanOrEqual(0)
+      const sshAction = src.indexOf('.action(async () => {', sshCmd)
+      const sshBlock = src.slice(sshCmd, sshAction)
+      expect(sshBlock).toContain(
+        "--yolo, --dangerously-skip-permissions",
+      )
+    })
+
+    it('is recognized by the cc:// and ssh raw-argv scans', async () => {
+      const src = await Bun.file(`${import.meta.dir}/../main.tsx`).text()
+      // cc:// sets remote state via includes(); the rewrites and ssh path strip
+      // both spellings from the forwarded argv.
+      expect(src).toContain(
+        "rawCliArgs.includes('--dangerously-skip-permissions') || rawCliArgs.includes('--yolo')",
+      )
+      expect(src).toContain("arg !== '--dangerously-skip-permissions' && arg !== '--yolo'")
+      expect(src).toContain(
+        "if (arg === '--dangerously-skip-permissions' || arg === '--yolo')",
+      )
+    })
+
+    it('strips both bypass spellings from cc:// and ssh forwarded argv', async () => {
+      const src = await Bun.file(`${import.meta.dir}/../main.tsx`).text()
+      // Passing both flags at once must not leave one behind as an unknown
+      // option on the headless `open` subcommand or in the ssh forwarded line.
+      const ccBlockStart = src.indexOf('Check for cc:// or cc+unix:// URL in argv')
+      const ccBlockEnd = src.indexOf('// Handle deep link URIs early', ccBlockStart)
+      const ccBlock = src.slice(ccBlockStart, ccBlockEnd)
+      const ccOccurrences =
+        ccBlock.split("'--dangerously-skip-permissions'").length - 1 +
+        ccBlock.split("'--yolo'").length - 1
+      expect(ccOccurrences).toBeGreaterThanOrEqual(4)
+
+      const sshBlockStart = src.indexOf("if (rawCliArgs[0] === 'ssh')")
+      const sshBlockEnd = src.indexOf('// else: `claude ssh` with no host', sshBlockStart)
+      const sshBlock = src.slice(sshBlockStart, sshBlockEnd)
+      expect(sshBlock).toContain(
+        "if (arg === '--dangerously-skip-permissions' || arg === '--yolo')",
+      )
+    })
+
+    it('is recognized by the skills leading scan so --yolo skills list routes', async () => {
+      const src = await Bun.file(`${import.meta.dir}/cli.tsx`).text()
+      const setStart = src.indexOf('SKILLS_LEADING_BOOLEAN_FLAGS = new Set([')
+      expect(setStart).toBeGreaterThanOrEqual(0)
+      const setEnd = src.indexOf(']', setStart)
+      const setBody = src.slice(setStart, setEnd)
+      expect(setBody).toContain("'--yolo'")
+    })
+
+    it('is recognized by the skills trailing scan so skills list --yolo routes', async () => {
+      const src = await Bun.file(
+        `${import.meta.dir}/../cli/handlers/skillsCli.ts`,
+      ).text()
+      const setStart = src.indexOf('TRAILING_GLOBAL_BOOLEAN_FLAGS = new Set([')
+      expect(setStart).toBeGreaterThanOrEqual(0)
+      const setEnd = src.indexOf(']', setStart)
+      const setBody = src.slice(setStart, setEnd)
+      expect(setBody).toContain("'--yolo'")
+    })
+
+    it('appears in the built CLI help', async () => {
+      const fs = await import('node:fs')
+      const path = await import('node:path')
+      const cliPath = path.resolve(import.meta.dir, '../../dist/cli.mjs')
+      expect(fs.existsSync(cliPath)).toBe(true)
+
+      const originalGuard = process.env.OPENCLAUDE_DISABLE_CLI_ENTRYPOINT_AUTO_RUN
+      delete process.env.OPENCLAUDE_DISABLE_CLI_ENTRYPOINT_AUTO_RUN
+      try {
+        const proc = Bun.spawn(['node', cliPath, '--help'], { stdout: 'pipe' })
+        const text = await new Response(proc.stdout).text()
+        await proc.exited
+        expect(text).toContain('--yolo, --dangerously-skip-permissions')
+      } finally {
+        if (originalGuard === undefined) {
+          delete process.env.OPENCLAUDE_DISABLE_CLI_ENTRYPOINT_AUTO_RUN
+        } else {
+          process.env.OPENCLAUDE_DISABLE_CLI_ENTRYPOINT_AUTO_RUN = originalGuard
+        }
+      }
+    })
+  })
 })
diff --git a/src/entrypoints/cli.tsx b/src/entrypoints/cli.tsx
index aa7c6034c..5a944f1a8 100644
--- a/src/entrypoints/cli.tsx
+++ b/src/entrypoints/cli.tsx
@@ -42,6 +42,7 @@ const SKILLS_LEADING_BOOLEAN_FLAGS = new Set([
   '--bare',
   '--debug',
   '--debug-to-stderr',
+  '--yolo',
   '--dangerously-skip-permissions',
   '--allow-dangerously-skip-permissions',
   '--disable-slash-commands',
diff --git a/src/main.tsx b/src/main.tsx
index be9171f38..f3cf6533d 100644
--- a/src/main.tsx
+++ b/src/main.tsx
@@ -589,24 +589,22 @@ export async function main() {
         parseConnectUrl
       } = await import('./server/parseConnectUrl.js');
       const parsed = parseConnectUrl(ccUrl);
-      _pendingConnect.dangerouslySkipPermissions = rawCliArgs.includes('--dangerously-skip-permissions');
+      _pendingConnect.dangerouslySkipPermissions = rawCliArgs.includes('--dangerously-skip-permissions') || rawCliArgs.includes('--yolo');
       if (rawCliArgs.includes('-p') || rawCliArgs.includes('--print')) {
-        // Headless: rewrite to internal `open` subcommand
-        const stripped = rawCliArgs.filter((_, i) => i !== ccIdx);
-        const dspIdx = stripped.indexOf('--dangerously-skip-permissions');
-        if (dspIdx !== -1) {
-          stripped.splice(dspIdx, 1);
-        }
+        // Headless: rewrite to internal `open` subcommand. Strip both the
+        // canonical flag and its alias — the `open` stub does not register
+        // either, and passing both would leave one behind as an unknown option.
+        const stripped = rawCliArgs
+          .filter((_, i) => i !== ccIdx)
+          .filter(arg => arg !== '--dangerously-skip-permissions' && arg !== '--yolo');
         process.argv = [process.argv[0]!, process.argv[1]!, 'open', ccUrl, ...stripped];
       } else {
-        // Interactive: strip cc:// URL and flags, run main command
+        // Interactive: strip cc:// URL and both bypass spellings, run main command
         _pendingConnect.url = parsed.serverUrl;
         _pendingConnect.authToken = parsed.authToken;
-        const stripped = rawCliArgs.filter((_, i) => i !== ccIdx);
-        const dspIdx = stripped.indexOf('--dangerously-skip-permissions');
-        if (dspIdx !== -1) {
-          stripped.splice(dspIdx, 1);
-        }
+        const stripped = rawCliArgs
+          .filter((_, i) => i !== ccIdx)
+          .filter(arg => arg !== '--dangerously-skip-permissions' && arg !== '--yolo');
         process.argv = [process.argv[0]!, process.argv[1]!, ...stripped];
       }
     }
@@ -688,10 +686,14 @@ export async function main() {
         _pendingSSH.local = true;
         rawCliArgs.splice(localIdx, 1);
       }
-      const dspIdx = rawCliArgs.indexOf('--dangerously-skip-permissions');
-      if (dspIdx !== -1) {
-        _pendingSSH.dangerouslySkipPermissions = true;
-        rawCliArgs.splice(dspIdx, 1);
+      // Remove both bypass spellings from the forwarded argv; the remote state
+      // is carried by _pendingSSH.dangerouslySkipPermissions, not by a flag.
+      for (let i = rawCliArgs.length - 1; i >= 0; i -= 1) {
+        const arg = rawCliArgs[i];
+        if (arg === '--dangerously-skip-permissions' || arg === '--yolo') {
+          _pendingSSH.dangerouslySkipPermissions = true;
+          rawCliArgs.splice(i, 1);
+        }
       }
       const pmIdx = rawCliArgs.indexOf('--permission-mode');
       if (pmIdx !== -1 && rawCliArgs[pmIdx + 1] && !rawCliArgs[pmIdx + 1]!.startsWith('-')) {
@@ -946,7 +948,7 @@ async function run(): Promise<CommanderCommand> {
     } catch (error) {
       throw new InvalidArgumentError(errorMessage(error));
     }
-  })).option('--bare', 'Minimal mode: skip hooks, LSP, plugin sync, attribution, auto-memory, background prefetches, keychain reads, and CLAUDE.md auto-discovery. Sets CLAUDE_CODE_SIMPLE=1. Anthropic auth is strictly ANTHROPIC_API_KEY or apiKeyHelper via --settings (OAuth and keychain are never read). 3P providers (Bedrock/Vertex/Foundry) use their own credentials. Skills still resolve via /skill-name. Explicitly provide context via: --system-prompt[-file], --append-system-prompt[-file], --add-dir (CLAUDE.md dirs), --mcp-config, --settings, --agents, --plugin-dir.', () => true).addOption(new Option('--init', 'Run Setup hooks with init trigger, then continue').hideHelp()).addOption(new Option('--init-only', 'Run Setup and SessionStart:startup hooks, then exit').hideHelp()).addOption(new Option('--maintenance', 'Run Setup hooks with maintenance trigger, then continue').hideHelp()).addOption(new Option('--output-format <format>', 'Output format (only works with --print): "text" (default), "json" (single result), or "stream-json" (realtime streaming)').choices(['text', 'json', 'stream-json'])).addOption(new Option('--json-schema <schema>', 'JSON Schema for structured output validation. ' + 'Example: {"type":"object","properties":{"name":{"type":"string"}},"required":["name"]}').argParser(String)).option('--include-hook-events', 'Include all hook lifecycle events in the output stream (only works with --output-format=stream-json)', () => true).option('--include-partial-messages', 'Include partial message chunks as they arrive (only works with --print and --output-format=stream-json)', () => true).addOption(new Option('--input-format <format>', 'Input format (only works with --print): "text" (default), or "stream-json" (realtime streaming input)').choices(['text', 'stream-json'])).option('--mcp-debug', '[DEPRECATED. Use --debug instead] Enable MCP debug mode (shows MCP server errors)', () => true).option('--dangerously-skip-permissions', 'Bypass all permission checks. Recommended only for sandboxes with no internet access.', () => true).option('--allow-dangerously-skip-permissions', 'Enable bypassing all permission checks as an option, without it being enabled by default. Recommended only for sandboxes with no internet access.', () => true).addOption(new Option('--thinking <mode>', 'Thinking mode: enabled (equivalent to adaptive), disabled').choices(['enabled', 'adaptive', 'disabled']).hideHelp()).addOption(new Option('--max-thinking-tokens <tokens>', '[DEPRECATED. Use --thinking instead for newer models] Maximum number of thinking tokens (only works with --print)').argParser(Number).hideHelp()).addOption(new Option('--max-turns <turns>', MAX_TURNS_CLI_DESCRIPTION).argParser(value => {
+  })).option('--bare', 'Minimal mode: skip hooks, LSP, plugin sync, attribution, auto-memory, background prefetches, keychain reads, and CLAUDE.md auto-discovery. Sets CLAUDE_CODE_SIMPLE=1. Anthropic auth is strictly ANTHROPIC_API_KEY or apiKeyHelper via --settings (OAuth and keychain are never read). 3P providers (Bedrock/Vertex/Foundry) use their own credentials. Skills still resolve via /skill-name. Explicitly provide context via: --system-prompt[-file], --append-system-prompt[-file], --add-dir (CLAUDE.md dirs), --mcp-config, --settings, --agents, --plugin-dir.', () => true).addOption(new Option('--init', 'Run Setup hooks with init trigger, then continue').hideHelp()).addOption(new Option('--init-only', 'Run Setup and SessionStart:startup hooks, then exit').hideHelp()).addOption(new Option('--maintenance', 'Run Setup hooks with maintenance trigger, then continue').hideHelp()).addOption(new Option('--output-format <format>', 'Output format (only works with --print): "text" (default), "json" (single result), or "stream-json" (realtime streaming)').choices(['text', 'json', 'stream-json'])).addOption(new Option('--json-schema <schema>', 'JSON Schema for structured output validation. ' + 'Example: {"type":"object","properties":{"name":{"type":"string"}},"required":["name"]}').argParser(String)).option('--include-hook-events', 'Include all hook lifecycle events in the output stream (only works with --output-format=stream-json)', () => true).option('--include-partial-messages', 'Include partial message chunks as they arrive (only works with --print and --output-format=stream-json)', () => true).addOption(new Option('--input-format <format>', 'Input format (only works with --print): "text" (default), or "stream-json" (realtime streaming input)').choices(['text', 'stream-json'])).option('--mcp-debug', '[DEPRECATED. Use --debug instead] Enable MCP debug mode (shows MCP server errors)', () => true).option('--yolo, --dangerously-skip-permissions', 'Bypass all permission checks. Recommended only for sandboxes with no internet access.', () => true).option('--allow-dangerously-skip-permissions', 'Enable bypassing all permission checks as an option, without it being enabled by default. Recommended only for sandboxes with no internet access.', () => true).addOption(new Option('--thinking <mode>', 'Thinking mode: enabled (equivalent to adaptive), disabled').choices(['enabled', 'adaptive', 'disabled']).hideHelp()).addOption(new Option('--max-thinking-tokens <tokens>', '[DEPRECATED. Use --thinking instead for newer models] Maximum number of thinking tokens (only works with --print)').argParser(Number).hideHelp()).addOption(new Option('--max-turns <turns>', MAX_TURNS_CLI_DESCRIPTION).argParser(value => {
     return parseMaxTurnsCommanderArgument(value);
   })).addOption(new Option('--max-budget-usd <amount>', 'Maximum dollar amount to spend on API calls (only works with --print)').argParser(value => {
     const amount = Number(value);
@@ -3912,7 +3914,7 @@ async function run(): Promise<CommanderCommand> {
   // this action it means the argv rewrite didn't fire (e.g. user ran
   // `claude ssh` with no host) — just print usage.
   if (feature('SSH_REMOTE')) {
-    program.command('ssh <host> [dir]').description('Run OpenClaude on a remote host over SSH. Deploys the binary and ' + 'tunnels API auth back through your local machine — no remote setup needed.').option('--permission-mode <mode>', 'Permission mode for the remote session').option('--dangerously-skip-permissions', 'Skip all permission prompts on the remote (dangerous)').option('--local', 'e2e test mode — spawn the child CLI locally (skip ssh/deploy). ' + 'Exercises the auth proxy and unix-socket plumbing without a remote host.').action(async () => {
+    program.command('ssh <host> [dir]').description('Run OpenClaude on a remote host over SSH. Deploys the binary and ' + 'tunnels API auth back through your local machine — no remote setup needed.').option('--permission-mode <mode>', 'Permission mode for the remote session').option('--yolo, --dangerously-skip-permissions', 'Skip all permission prompts on the remote (dangerous)').option('--local', 'e2e test mode — spawn the child CLI locally (skip ssh/deploy). ' + 'Exercises the auth proxy and unix-socket plumbing without a remote host.').action(async () => {
       // Argv rewriting in main() should have consumed `ssh <host>` before
       // commander runs. Reaching here means host was missing or the
       // rewrite predicate didn't match.
diff --git a/web/src/data/cliFlags.ts b/web/src/data/cliFlags.ts
index 27a93936e..61f31ccf8 100644
--- a/web/src/data/cliFlags.ts
+++ b/web/src/data/cliFlags.ts
@@ -83,7 +83,7 @@ export const flagGroups: FlagGroup[] = [
       { flag: '--allowed-tools', arg: '<tools...>', description: 'Comma or space-separated list of tool rules to allow (e.g. "Bash(git:*) Edit").' },
       { flag: '--disallowed-tools', arg: '<tools...>', description: 'Comma or space-separated list of tool rules to deny.' },
       { flag: '--tools', arg: '<tools...>', description: 'Restrict the built-in tool set: "" disables all tools, "default" enables all, or list names like "Bash,Edit,Read".' },
-      { flag: '--dangerously-skip-permissions', description: 'Bypass all permission checks. Recommended only for sandboxes with no internet access.' },
+      { flag: '--yolo, --dangerously-skip-permissions', description: 'Bypass all permission checks. Recommended only for sandboxes with no internet access.' },
       { flag: '--allow-dangerously-skip-permissions', description: 'Make permission bypass available as an option without enabling it by default.' },
       { flag: '--add-dir', arg: '<dirs...>', description: 'Additional directories to allow tool access to.' },
     ],