diff --git a/packages/mosaic/src/fleet/fleet-documentation.spec.ts b/packages/mosaic/src/fleet/fleet-documentation.spec.ts
index addfb1d..bc9fb8a 100644
--- a/packages/mosaic/src/fleet/fleet-documentation.spec.ts
+++ b/packages/mosaic/src/fleet/fleet-documentation.spec.ts
@@ -131,17 +131,117 @@ function markdownLinkViolations(
   return violations;
 }
 
+function commandBasename(token: string): string {
+  return token.slice(token.lastIndexOf('/') + 1);
+}
+
+function normalizedCommandTokens(segment: string): string[] {
+  const tokens = segment
+    .trim()
+    .replace(/^(?:[$#>]\s*)/, '')
+    .split(/\s+/)
+    .filter((token): boolean => token !== '');
+  let index = 0;
+
+  while (index < tokens.length) {
+    const wrapper = commandBasename(tokens[index] ?? '');
+    if (wrapper === 'env') {
+      index += 1;
+      while (index < tokens.length) {
+        const token = tokens[index] ?? '';
+        if (/^[A-Za-z_][A-Za-z0-9_]*=/.test(token)) {
+          index += 1;
+          continue;
+        }
+        if (/^(?:-u|--unset|-C|--chdir)$/.test(token)) {
+          index += 2;
+          continue;
+        }
+        if (/^(?:-u|--unset=|-C|--chdir=)/.test(token)) {
+          index += 1;
+          continue;
+        }
+        if (/^(?:-S|--split-string)$/.test(token)) {
+          index += 1;
+          break;
+        }
+        if (token.startsWith('-')) {
+          index += 1;
+          continue;
+        }
+        break;
+      }
+      continue;
+    }
+    if (wrapper === 'command') {
+      index += 1;
+      while ((tokens[index] ?? '').startsWith('-')) index += 1;
+      continue;
+    }
+    break;
+  }
+
+  return tokens.slice(index);
+}
+
+function containsPrivilegedCommand(source: string): boolean {
+  const privilegedCommands = new Set([
+    'sudo',
+    'doas',
+    'pkexec',
+    'systemctl',
+    'service',
+    'mount',
+    'umount',
+    'reboot',
+    'shutdown',
+    'poweroff',
+    'halt',
+    'chown',
+    'chmod',
+    'chroot',
+    'useradd',
+    'usermod',
+    'groupadd',
+    'visudo',
+    'apt',
+    'apt-get',
+    'apt-cache',
+    'dpkg',
+    'yum',
+    'dnf',
+    'rpm',
+    'apk',
+    'pacman',
+    'zypper',
+    'emerge',
+    'snap',
+    'flatpak',
+    'brew',
+    'nix-env',
+  ]);
+
+  return source.split(/[\n;&|]+/).some((segment): boolean => {
+    const tokens = normalizedCommandTokens(segment);
+    const command = commandBasename(tokens[0] ?? '');
+    if (privilegedCommands.has(command)) return true;
+    const argument = tokens[1] ?? '';
+    return (
+      command === 'su' &&
+      (/^(?:root|-|--command|-c)$/.test(argument) || argument.startsWith('--command='))
+    );
+  });
+}
+
 function exampleSafetyViolationKinds(source: string): string[] {
   const kinds = new Set<string>();
   const sensitiveKey = /(?:secret|token|password|credential|MOSAIC_AGENT_COMMAND)/i;
   const credentialFormat =
     /(?:\bAKIA[0-9A-Z]{16}\b|\bAIza[0-9A-Za-z_-]{35}\b|\bgh[pousr]_[A-Za-z0-9]{20,}\b|\bgithub_pat_[A-Za-z0-9_]{20,}\b|\bglpat-[A-Za-z0-9_-]{20,}\b|\bnpm_[A-Za-z0-9]{20,}\b|\bsk-ant-(?:api\d{2}-)?[A-Za-z0-9_-]{20,}\b|\bsk-proj-[A-Za-z0-9_-]{20,}\b|\b(?:sk|rk)_(?:live|test)_[A-Za-z0-9]{16,}\b|\bxox[baprs]-[A-Za-z0-9-]{10,}\b|\bBearer\s+[A-Za-z0-9._~+/=-]{16,}\b|\beyJ[A-Za-z0-9_-]{8,}\.[A-Za-z0-9_-]{8,}\.[A-Za-z0-9_-]{8,}\b|-----BEGIN [A-Z ]*PRIVATE KEY-----|\b[A-Za-z][A-Za-z0-9+.-]*:\/\/[^\s/:]+:[^\s/@]+@)/;
-  const privilegedCommand =
-    /(?:^|[\n;&|])\s*(?:[$#>]\s*)?(?:(?:\/(?:[A-Za-z0-9._+-]+\/)*?)?(?:env|command)\s+(?:(?:-{1,2}[^\s]+|[A-Za-z_][A-Za-z0-9_]*=[^\s]+)\s+)*?)*(?:\/(?:[A-Za-z0-9._+-]+\/)*?)?(?:(?:sudo|doas|pkexec)\s+|su\s+(?:root\b|-|--command\b|-c\b)|(?:systemctl|service|mount|umount|reboot|shutdown|poweroff|halt|chown|chmod|chroot|useradd|usermod|groupadd|visudo|apt|apt-get|apt-cache|dpkg|yum|dnf|rpm|apk|pacman|zypper|emerge|snap|flatpak|brew|nix-env)\s+)/m;
 
   if (sensitiveKey.test(source)) kinds.add('sensitive-key');
   if (credentialFormat.test(source)) kinds.add('credential-format');
-  if (privilegedCommand.test(source)) kinds.add('privileged-command');
+  if (containsPrivilegedCommand(source)) kinds.add('privileged-command');
   if (/\b(?:Tess|Ultron)\b/.test(source)) kinds.add('identity');
   return [...kinds].sort();
 }
@@ -189,6 +289,17 @@ const UNSAFE_EXAMPLE_FIXTURES = [
     expected: 'privileged-command',
     source: '/usr/bin/env -i /usr/bin/command -- /usr/bin/apt-get install example',
   },
+  {
+    expected: 'privileged-command',
+    source: '/usr/bin/env -u FOO /usr/bin/apt-get install example',
+  },
+  {
+    expected: 'privileged-command',
+    source: 'env --unset FOO /usr/bin/apt-get install example',
+  },
+  { expected: 'privileged-command', source: 'env -S apt-get install example' },
+  { expected: 'privileged-command', source: 'reboot' },
+  { expected: 'privileged-command', source: 'su --command=/bin/sh' },
   { expected: 'privileged-command', source: 'su root' },
   { expected: 'privileged-command', source: '/usr/sbin/chroot /srv/example' },
   { expected: 'credential-format', source: ['ghp_', 'a'.repeat(36)].join('') },