diff --git a/src/common/utils/__tests__/paths.test.ts b/src/common/utils/__tests__/paths.test.ts
new file mode 100644
index 0000000000..0eec289fb9
--- /dev/null
+++ b/src/common/utils/__tests__/paths.test.ts
@@ -0,0 +1,130 @@
+/**
+ * Copyright (c) 2021 OpenLens Authors
+ *
+ * Permission is hereby granted, free of charge, to any person obtaining a copy of
+ * this software and associated documentation files (the "Software"), to deal in
+ * the Software without restriction, including without limitation the rights to
+ * use, copy, modify, merge, publish, distribute, sublicense, and/or sell copies of
+ * the Software, and to permit persons to whom the Software is furnished to do so,
+ * subject to the following conditions:
+ *
+ * The above copyright notice and this permission notice shall be included in all
+ * copies or substantial portions of the Software.
+ *
+ * THE SOFTWARE IS PROVIDED "AS IS", WITHOUT WARRANTY OF ANY KIND, EXPRESS OR
+ * IMPLIED, INCLUDING BUT NOT LIMITED TO THE WARRANTIES OF MERCHANTABILITY, FITNESS
+ * FOR A PARTICULAR PURPOSE AND NONINFRINGEMENT. IN NO EVENT SHALL THE AUTHORS OR
+ * COPYRIGHT HOLDERS BE LIABLE FOR ANY CLAIM, DAMAGES OR OTHER LIABILITY, WHETHER
+ * IN AN ACTION OF CONTRACT, TORT OR OTHERWISE, ARISING FROM, OUT OF OR IN
+ * CONNECTION WITH THE SOFTWARE OR THE USE OR OTHER DEALINGS IN THE SOFTWARE.
+ */
+
+import { describeIf } from "../../../../integration/helpers/utils";
+import { isWindows } from "../../vars";
+import { isLogicalChildPath } from "../paths";
+
+describe("isLogicalChildPath", () => {
+  describeIf(isWindows)("windows tests", () => {
+    it.each([
+      {
+        parentPath: "C:\\Foo",
+        testPath: "C:\\Foo\\Bar",
+        expected: true,
+      },
+      {
+        parentPath: "C:\\Foo",
+        testPath: "C:\\Bar",
+        expected: false,
+      },
+      {
+        parentPath: "C:\\Foo",
+        testPath: "C:/Bar",
+        expected: false,
+      },
+      {
+        parentPath: "C:\\Foo",
+        testPath: "C:/Foo/Bar",
+        expected: true,
+      },
+      {
+        parentPath: "C:\\Foo",
+        testPath: "D:\\Foo\\Bar",
+        expected: false,
+      },
+    ])("test %#", (testData) => {
+      expect(isLogicalChildPath(testData.parentPath, testData.testPath)).toBe(testData.expected);
+    });
+  });
+
+  describeIf(!isWindows)("posix tests", () => {
+    it.each([
+      {
+        parentPath: "/foo",
+        testPath: "/foo",
+        expected: false,
+      },
+      {
+        parentPath: "/foo",
+        testPath: "/bar",
+        expected: false,
+      },
+      {
+        parentPath: "/foo",
+        testPath: "/foobar",
+        expected: false,
+      },
+      {
+        parentPath: "/foo",
+        testPath: "/foo/bar",
+        expected: true,
+      },
+      {
+        parentPath: "/foo",
+        testPath: "/foo/../bar",
+        expected: false,
+      },
+      {
+        parentPath: "/foo",
+        testPath: "/foo/./bar",
+        expected: true,
+      },
+      {
+        parentPath: "/foo",
+        testPath: "/foo/.bar",
+        expected: true,
+      },
+      {
+        parentPath: "/foo",
+        testPath: "/foo/..bar",
+        expected: true,
+      },
+      {
+        parentPath: "/foo",
+        testPath: "/foo/...bar",
+        expected: true,
+      },
+      {
+        parentPath: "/foo",
+        testPath: "/foo/..\\.bar",
+        expected: true,
+      },
+      {
+        parentPath: "/bar/../foo",
+        testPath: "/foo/bar",
+        expected: true,
+      },
+      {
+        parentPath: "/foo",
+        testPath: "/foo/\\bar",
+        expected: true,
+      },
+      {
+        parentPath: "/foo",
+        testPath: "./bar",
+        expected: false,
+      },
+    ])("test %#", (testData) => {
+      expect(isLogicalChildPath(testData.parentPath, testData.testPath)).toBe(testData.expected);
+    });
+  });
+});
diff --git a/src/common/utils/paths.ts b/src/common/utils/paths.ts
index 391e1392f2..68d8f61ffa 100644
--- a/src/common/utils/paths.ts
+++ b/src/common/utils/paths.ts
@@ -33,3 +33,35 @@ function resolveTilde(filePath: string) {
 export function resolvePath(filePath: string): string {
   return path.resolve(resolveTilde(filePath));
 }
+
+/**
+ * Checks if `testPath` represents a potential filesystem entry that would be
+ * logically "within" the `parentPath` directory.
+ *
+ * This function will return `true` in the above case, and `false` otherwise.
+ * It will return `false` if the two paths are the same (after resolving them).
+ *
+ * The function makes no FS calls and is platform dependant. Meaning that the
+ * results are only guaranteed to be correct for the platform you are running
+ * on.
+ * @param parentPath The known path of a directory
+ * @param testPath The path that is to be tested
+ */
+export function isLogicalChildPath(parentPath: string, testPath: string): boolean {
+  parentPath = path.resolve(parentPath);
+  testPath = path.resolve(testPath);
+
+  if (parentPath === testPath) {
+    return false;
+  }
+
+  while (testPath.length >= parentPath.length) {
+    if (testPath === parentPath) {
+      return true;
+    }
+
+    testPath = path.dirname(testPath);
+  }
+
+  return false;
+}
diff --git a/src/migrations/user-store/5.0.3-beta.1.ts b/src/migrations/user-store/5.0.3-beta.1.ts
index 72f3899627..ef3448116d 100644
--- a/src/migrations/user-store/5.0.3-beta.1.ts
+++ b/src/migrations/user-store/5.0.3-beta.1.ts
@@ -26,6 +26,7 @@ import os from "os";
 import { ClusterStore, ClusterStoreModel } from "../../common/cluster-store";
 import type { KubeconfigSyncEntry, UserPreferencesModel } from "../../common/user-store";
 import { MigrationDeclaration, migrationLog } from "../helpers";
+import { isLogicalChildPath } from "../../common/utils";
 
 export default {
   version: "5.0.3-beta.1",
@@ -36,7 +37,6 @@ export default {
       const extensionDataDir = path.resolve(app.getPath("userData"), "extension_data");
       const syncPaths = new Set(syncKubeconfigEntries.map(s => s.filePath));
 
-      console.log(extensionDataDir);
       syncPaths.add(path.join(os.homedir(), ".kube"));
 
       for (const cluster of clusters) {
@@ -52,9 +52,7 @@ export default {
           continue;
         }
 
-        const relativeToExtensionData = path.relative(cluster.kubeConfigPath, extensionDataDir);
-
-        if (relativeToExtensionData === "" || relativeToExtensionData.match(/^(\.\.)([\\\/]\.\.)*$/)) {
+        if (isLogicalChildPath(extensionDataDir, cluster.kubeConfigPath)) {
           migrationLog(`Skipping ${cluster.id} because kubeConfigPath is placed under an extension_data folder`);
           continue;
         }