diff --git a/src/permission/fs_permission.h b/src/permission/fs_permission.h
index b009b66f6485..2b24e04a112f 100644
--- a/src/permission/fs_permission.h
+++ b/src/permission/fs_permission.h
@@ -54,7 +54,9 @@ class FSPermission final : public PermissionBase {
       }
 
       Node* CreateChild(std::string_view path_prefix) {
-        if (path_prefix.empty() && !is_leaf) {
+        // An empty remaining prefix means this node already represents the
+        // inserted path. Re-inserting it is a no-op.
+        if (path_prefix.empty()) {
           is_leaf = true;
           return this;
         }
diff --git a/test/parallel/test-permission-drop-colliding-wildcards.js b/test/parallel/test-permission-drop-colliding-wildcards.js
new file mode 100644
index 000000000000..5b9a5512640f
--- /dev/null
+++ b/test/parallel/test-permission-drop-colliding-wildcards.js
@@ -0,0 +1,87 @@
+// Flags: --permission --allow-fs-read=* --allow-child-process
+'use strict';
+
+// Regression test for https://github.com/nodejs/node/issues/66901
+//
+// Two --allow-fs-read grants that are identical up to and including their
+// first `*` are deduplicated by GrantAccess, so the colliding insert never
+// happens while the flags are applied. permission.drop() calls RebuildTree,
+// which replays the recorded grant list unconditionally, and the second
+// insert reached an unconditional CHECK in Node::CreateChild and aborted
+// the process with SIGABRT.
+
+const common = require('../common');
+const { isMainThread } = require('worker_threads');
+
+if (!isMainThread) {
+  common.skip('This test only works on a main thread');
+}
+
+const assert = require('assert');
+const path = require('path');
+const { spawnSync } = require('child_process');
+const tmpdir = require('../common/tmpdir');
+
+tmpdir.refresh();
+
+const dir = path.join(tmpdir.path, 'sig');
+const script = path.join(dir, 'app.js');
+
+require('fs').mkdirSync(dir, { recursive: true });
+require('fs').writeFileSync(
+  script,
+  'process.permission.drop("fs.read", process.argv[1]);\n' +
+  'console.log("survived");\n',
+);
+
+{
+  // Colliding grants plus a drop() must not abort the process.
+  const { status, signal, stdout, stderr } = spawnSync(
+    process.execPath,
+    [
+      '--permission',
+      `--allow-fs-read=${path.join(dir, '*')}`,
+      `--allow-fs-read=${path.join(dir, '*.js')}`,
+      script,
+    ],
+    { encoding: 'utf8' },
+  );
+
+  assert.strictEqual(signal, null, `killed by ${signal}\n${stderr}`);
+  assert.strictEqual(status, 0, `exited ${status}\n${stderr}`);
+  assert.match(stdout, /survived/);
+}
+
+{
+  // Control: a single grant with the same drop() already worked, and must
+  // keep working.
+  const { status, signal } = spawnSync(
+    process.execPath,
+    ['--permission', `--allow-fs-read=${path.join(dir, '*')}`, script],
+    { encoding: 'utf8' },
+  );
+
+  assert.strictEqual(signal, null);
+  assert.strictEqual(status, 0);
+}
+
+{
+  // The colliding grants must still grant what they say they grant.
+  const probe = path.join(dir, 'probe.txt');
+  require('fs').writeFileSync(probe, 'ok');
+
+  const { status, stdout, stderr } = spawnSync(
+    process.execPath,
+    [
+      '--permission',
+      `--allow-fs-read=${path.join(dir, '*')}`,
+      `--allow-fs-read=${path.join(dir, '*.js')}`,
+      '-e',
+      `console.log(require('fs').readFileSync(${JSON.stringify(probe)}, 'utf8'));`,
+    ],
+    { encoding: 'utf8' },
+  );
+
+  assert.strictEqual(status, 0, stderr);
+  assert.match(stdout, /ok/);
+}