diff --git a/packages/mosaic/src/fleet/fleet-documentation.spec.ts b/packages/mosaic/src/fleet/fleet-documentation.spec.ts
index bab73f2..08a61e2 100644
--- a/packages/mosaic/src/fleet/fleet-documentation.spec.ts
+++ b/packages/mosaic/src/fleet/fleet-documentation.spec.ts
@@ -135,12 +135,64 @@ function commandBasename(token: string): string {
   return token.slice(token.lastIndexOf('/') + 1);
 }
 
+function shellCommandSegments(source: string): string[] {
+  const segments: string[] = [];
+  let segment = '';
+  let quote = '';
+  let escaped = false;
+
+  const flush = (): void => {
+    if (segment.trim() !== '') segments.push(segment);
+    segment = '';
+  };
+
+  for (const character of source) {
+    if (escaped) {
+      segment += character;
+      escaped = false;
+      continue;
+    }
+    if (character === '\\' && quote !== "'") {
+      segment += character;
+      escaped = true;
+      continue;
+    }
+    if (quote !== '') {
+      segment += character;
+      if (character === quote) quote = '';
+      continue;
+    }
+    if (character === "'" || character === '"') {
+      segment += character;
+      quote = character;
+      continue;
+    }
+    if (character === '\n' || character === ';' || character === '&' || character === '|') {
+      flush();
+      continue;
+    }
+    segment += character;
+  }
+  flush();
+  return segments;
+}
+
 function shellCommandTokens(source: string): string[] {
   const tokens: string[] = [];
   let token = '';
   let quote = '';
+  let escaped = false;
 
   for (const character of source) {
+    if (escaped) {
+      token += character;
+      escaped = false;
+      continue;
+    }
+    if (character === '\\' && quote !== "'") {
+      escaped = true;
+      continue;
+    }
     if (quote !== '') {
       if (character === quote) quote = '';
       else token += character;
@@ -159,6 +211,7 @@ function shellCommandTokens(source: string): string[] {
     }
     token += character;
   }
+  if (escaped) token += '\\';
   if (token !== '') tokens.push(token);
   return tokens;
 }
@@ -177,22 +230,47 @@ function normalizedCommandTokens(segment: string): string[] {
           index += 1;
           continue;
         }
-        if (/^(?:-u|--unset|-C|--chdir)$/.test(token)) {
+        if (token === '--') {
+          index += 1;
+          break;
+        }
+        if (/^(?:--unset|--chdir)$/.test(token)) {
           index += 2;
           continue;
         }
-        if (/^(?:-u|--unset=|-C|--chdir=)/.test(token)) {
+        if (/^(?:--unset=|--chdir=)/.test(token)) {
           index += 1;
           continue;
         }
-        if (/^(?:-S|--split-string)$/.test(token)) {
+        if (token === '--split-string') {
           const splitTokens = shellCommandTokens(tokens[index + 1] ?? '');
           tokens.splice(index, 2, ...splitTokens);
           continue;
         }
-        const splitString = token.match(/^(?:-S|--split-string=)(.*)$/)?.[1];
-        if (splitString !== undefined) {
-          tokens.splice(index, 1, ...shellCommandTokens(splitString));
+        const longSplitString = token.match(/^--split-string=(.*)$/)?.[1];
+        if (longSplitString !== undefined) {
+          tokens.splice(index, 1, ...shellCommandTokens(longSplitString));
+          continue;
+        }
+        if (/^-[^-]/.test(token)) {
+          const options = token.slice(1);
+          let consumed = false;
+          for (let optionIndex = 0; optionIndex < options.length; optionIndex += 1) {
+            const option = options[optionIndex] ?? '';
+            if (option === 'u' || option === 'C') {
+              index += options.slice(optionIndex + 1) === '' ? 2 : 1;
+              consumed = true;
+              break;
+            }
+            if (option === 'S') {
+              const attached = options.slice(optionIndex + 1);
+              const operand = attached === '' ? (tokens[index + 1] ?? '') : attached;
+              tokens.splice(index, attached === '' ? 2 : 1, ...shellCommandTokens(operand));
+              consumed = true;
+              break;
+            }
+          }
+          if (!consumed) index += 1;
           continue;
         }
         if (token.startsWith('-')) {
@@ -258,7 +336,7 @@ function containsPrivilegedCommand(source: string): boolean {
     'nix-env',
   ]);
 
-  return source.split(/[\n;&|]+/).some((segment): boolean => {
+  return shellCommandSegments(source).some((segment): boolean => {
     const tokens = normalizedCommandTokens(segment);
     const command = commandBasename(tokens[0] ?? '');
     if (privilegedCommands.has(command)) return true;
@@ -272,7 +350,7 @@ function containsPrivilegedCommand(source: string): boolean {
         break;
       }
       if (
-        /^(?:-c|--command|--session-command|-g|--group|-G|--supp-group|-s|--shell|-w|--whitelist-environment)$/.test(
+        /^(?:--command|--session-command|--group|--supp-group|--shell|--whitelist-environment)$/.test(
           token,
         )
       ) {
@@ -287,13 +365,28 @@ function containsPrivilegedCommand(source: string): boolean {
         index += 1;
         continue;
       }
+      if (/^-[^-]/.test(token)) {
+        const options = token.slice(1);
+        let consumed = false;
+        for (let optionIndex = 0; optionIndex < options.length; optionIndex += 1) {
+          const option = options[optionIndex] ?? '';
+          if ('cgGsw'.includes(option)) {
+            index += options.slice(optionIndex + 1) === '' ? 2 : 1;
+            consumed = true;
+            break;
+          }
+        }
+        if (!consumed) index += 1;
+        continue;
+      }
       if (token.startsWith('-')) {
         index += 1;
         continue;
       }
       break;
     }
-    return (tokens[index] ?? 'root') === 'root';
+    const user = tokens[index];
+    return user === undefined || user === 'root';
   });
 }
 
@@ -357,6 +450,14 @@ const UNSAFE_EXAMPLE_FIXTURES = [
     expected: 'privileged-command',
     source: '/usr/bin/env -u FOO /usr/bin/apt-get install example',
   },
+  {
+    expected: 'privileged-command',
+    source: 'env -iu FOO /usr/bin/apt-get --version',
+  },
+  {
+    expected: 'privileged-command',
+    source: 'env -ivS/usr/bin/apt-get --version',
+  },
   {
     expected: 'privileged-command',
     source: 'env --unset FOO /usr/bin/apt-get install example',
@@ -382,6 +483,7 @@ const UNSAFE_EXAMPLE_FIXTURES = [
   },
   { expected: 'privileged-command', source: 'reboot' },
   { expected: 'privileged-command', source: 'su --command=/bin/sh' },
+  { expected: 'privileged-command', source: 'su -lc /usr/bin/id' },
   { expected: 'privileged-command', source: 'su -l root' },
   { expected: 'privileged-command', source: 'su -l -s /bin/sh root' },
   { expected: 'privileged-command', source: '/usr/bin/su --login root' },
@@ -440,9 +542,24 @@ describe('documentation validation regressions', (): void => {
     expect(exampleSafetyViolationKinds('command -v apt-get')).not.toContain('privileged-command');
   });
 
+  it('keeps quoted command separators as inert argument data', (): void => {
+    expect(
+      exampleSafetyViolationKinds("printf '%s\\n' 'safe; /usr/bin/apt-get update'"),
+    ).not.toContain('privileged-command');
+  });
+
+  it('still detects commands after unquoted command separators', (): void => {
+    expect(exampleSafetyViolationKinds('printf safe; /usr/bin/apt-get update')).toContain(
+      'privileged-command',
+    );
+  });
+
   it.each([
     "env --split-string='-i -- /usr/bin/printf safe'",
     "env --split-string='FOO=x /usr/bin/printf safe'",
+    'env -iu FOO /usr/bin/printf safe',
+    'env -ivS/usr/bin/printf safe',
+    'su -lc /usr/bin/id operator',
     'su -l -s /bin/sh operator',
     'su -s /bin/sh -- operator',
     'su -c /usr/bin/id operator',