diff --git a/lib/child_process.js b/lib/child_process.js
index 6b411f43f07..668b000398f 100644
--- a/lib/child_process.js
+++ b/lib/child_process.js
@@ -568,6 +568,11 @@ function hasPermissionFlagInEnv(nodeOptions) {
   );
 }
 
+function quoteNodeOption(flag, value) {
+  const quoted = RegExpPrototypeSymbolReplace(/["\\]/g, value, '\\$&');
+  return `"${flag}=${quoted}"`;
+}
+
 function copyPermissionModelFlagsToEnv(env, key, args) {
   // Do not override if permission was already passed to file
   if (args.includes('--permission') || args.includes('--permission-audit') ||
@@ -582,15 +587,33 @@ function copyPermissionModelFlagsToEnv(env, key, args) {
 
   const flagsToCopy = getPermissionModelFlagsToCopy();
   const copiedFlags = new SafeSet();
-  for (const arg of process.execArgv) {
+  const execArgv = process.execArgv;
+  for (let i = 0; i < execArgv.length; i++) {
+    const arg = execArgv[i];
     if (allowAllEnv && arg.startsWith('--allow-env')) {
       continue;
     }
     for (const flag of flagsToCopy) {
-      if (arg.startsWith(flag)) {
-        copiedFlags.add(flag);
-        env[key] = `${env[key] ? env[key] + ' ' + arg : arg}`;
+      if (!arg.startsWith(flag)) {
+        continue;
+      }
+      copiedFlags.add(flag);
+      if (ArrayIsArray(getOptionValue(flag))) {
+        let value;
+        if (arg === flag && i + 1 < execArgv.length) {
+          value = execArgv[++i];
+          if (value[0] === '\\' && value[1] === '-') {
+            value = StringPrototypeSlice(value, 1);
+          }
+        } else if (arg[flag.length] === '=') {
+          value = StringPrototypeSlice(arg, flag.length + 1);
+        }
+        if (value !== undefined) {
+          env[key] = `${env[key] ? env[key] + ' ' : ''}${quoteNodeOption(flag, value)}`;
+          break;
+        }
       }
+      env[key] = `${env[key] ? env[key] + ' ' + arg : arg}`;
     }
   }
 
@@ -604,10 +627,7 @@ function copyPermissionModelFlagsToEnv(env, key, args) {
       env[key] = `${env[key] ? env[key] + ' ' : ''}${flag}`;
     } else if (ArrayIsArray(value)) {
       for (const item of value) {
-        // Values may contain spaces or quotes (e.g. the implicitly allowed
-        // entry point), so quote them as NODE_OPTIONS expects.
-        const quoted = RegExpPrototypeSymbolReplace(/["\\]/g, item, '\\$&');
-        env[key] = `${env[key] ? env[key] + ' ' : ''}"${flag}=${quoted}"`;
+        env[key] = `${env[key] ? env[key] + ' ' : ''}${quoteNodeOption(flag, item)}`;
       }
     }
   }
diff --git a/test/parallel/test-permission-child-process-inherit-flags.js b/test/parallel/test-permission-child-process-inherit-flags.js
index 36e89bfb1c7..808be87c3ec 100644
--- a/test/parallel/test-permission-child-process-inherit-flags.js
+++ b/test/parallel/test-permission-child-process-inherit-flags.js
@@ -100,6 +100,51 @@ const childProcess = require('child_process');
   assert.strictEqual(worker, 'false');
 }
 
+{
+  const tmpdir = require('../common/tmpdir');
+  const dir = tmpdir.resolve('inherit flags dir');
+  const file = `${dir}/file.txt`;
+
+  const grandchildSource = `
+    console.log(process.permission.has('fs.read'));
+    console.log(process.permission.has('fs.read', ${JSON.stringify(file)}));
+    console.log(process.permission.has('fs.read', ${JSON.stringify(__filename)}));
+  `;
+  const childSource = `
+    const { status, stdout, stderr } = require('child_process').spawnSync(
+      process.execPath, ['-e', ${JSON.stringify(grandchildSource)}]);
+    console.log(JSON.stringify({
+      status,
+      stderr: stderr.toString(),
+      permissions: stdout.toString().trim().split('\\n'),
+    }));
+  `;
+
+  function run(args) {
+    const { status, stdout, stderr } = childProcess.spawnSync(
+      process.execPath,
+      ['--permission', '--allow-child-process', ...args, '-e', childSource],
+    );
+    assert.strictEqual(status, 0, stderr.toString());
+    const grandchild = JSON.parse(stdout.toString());
+    assert.strictEqual(grandchild.status, 0, grandchild.stderr);
+    return grandchild.permissions;
+  }
+
+  assert.deepStrictEqual(run(['--allow-fs-read', '*']),
+                         ['true', 'true', 'true']);
+
+  assert.deepStrictEqual(run(['--allow-fs-read', `${dir}/*`]),
+                         ['false', 'true', 'false']);
+
+  assert.deepStrictEqual(run([`--allow-fs-read=${dir}/*`]),
+                         ['false', 'true', 'false']);
+
+  assert.deepStrictEqual(
+    run(['--allow-fs-read', `${dir}/*`, `--allow-fs-read=${__filename}`]),
+    ['false', 'true', 'true']);
+}
+
 {
   assert.strictEqual(process.env.NODE_OPTIONS, undefined);
 }