diff --git a/src/runner.ts b/src/runner.ts
index 61651ab..764030e 100644
--- a/src/runner.ts
+++ b/src/runner.ts
@@ -451,7 +451,7 @@ export class TestRunner {
   }
 }
 
-class CompiledFileTests {
+export class CompiledFileTests {
   public readonly value = new Map</* compiled file path */ string, /* source file test items */ Set<vscode.TestItem>>();
 
   /**
@@ -476,10 +476,13 @@ class CompiledFileTests {
 
   /**
    * Gets a test item by its path of titles in the test file.
+   * Falls back to the deepest matched ancestor when the full path
+   * can't be resolved (e.g. when tests are dynamically generated).
    */
   private getPathInTestItems(items: Set<vscode.TestItem>, path: readonly string[]) {
     for (const item of items) {
       let candidate: vscode.TestItem | undefined = item;
+      let deepestMatch: vscode.TestItem | undefined;
       for (let i = 0; i < path.length && candidate; i++) {
         const pathPart = path[i];
         if (
@@ -490,11 +493,20 @@ class CompiledFileTests {
         ) {
           break;
         }
-        candidate = candidate.children.get(pathPart);
+        const next = candidate.children.get(pathPart);
+        if (next) {
+          deepestMatch = next;
+          candidate = next;
+        } else {
+          candidate = undefined;
+        }
       }
       if (candidate !== undefined) {
         return candidate;
       }
+      if (deepestMatch !== undefined) {
+        return deepestMatch;
+      }
     }
   }
 
diff --git a/src/test/unit/runner.test.ts b/src/test/unit/runner.test.ts
new file mode 100644
index 0000000..ddf1212
--- /dev/null
+++ b/src/test/unit/runner.test.ts
@@ -0,0 +1,103 @@
+/**
+ * Copyright (C) Daniel Kuschny (Danielku15) and contributors.
+ * Copyright (C) Microsoft Corporation. All rights reserved.
+ *
+ * Use of this source code is governed by an MIT-style
+ * license that can be found in the LICENSE file or at
+ * https://opensource.org/licenses/MIT.
+ */
+
+import { expect } from 'chai';
+import type * as vscode from 'vscode';
+import { CompiledFileTests } from '../../runner';
+
+/** Minimal mock that satisfies the subset of vscode.TestItem used by CompiledFileTests. */
+function mockTestItem(id: string, childItems: vscode.TestItem[] = []): vscode.TestItem {
+  const childMap = new Map<string, vscode.TestItem>();
+  for (const child of childItems) {
+    childMap.set(child.id, child);
+  }
+  return {
+    id,
+    label: id,
+    children: {
+      get: (key: string) => childMap.get(key),
+      size: childMap.size,
+    },
+  } as unknown as vscode.TestItem;
+}
+
+describe('CompiledFileTests', () => {
+  const FILE = '/project/out/test.js';
+
+  function buildTree() {
+    const cft = new CompiledFileTests();
+
+    const test1 = mockTestItem('test1');
+    const test2 = mockTestItem('test2');
+    const innerSuite = mockTestItem('innerSuite', [mockTestItem('deep')]);
+    const suite = mockTestItem('suite', [test1, test2, innerSuite]);
+    const fileItem = mockTestItem('file', [suite]);
+
+    cft.push(FILE, fileItem);
+    return { cft, fileItem, suite, test1, test2, innerSuite };
+  }
+
+  describe('lookup', () => {
+    it('returns the exact item for a fully matching path', () => {
+      const { cft, test1 } = buildTree();
+      expect(cft.lookup(FILE, ['suite', 'test1'])).to.equal(test1);
+    });
+
+    it('returns a nested item through multiple levels', () => {
+      const { cft, innerSuite } = buildTree();
+      const deep = innerSuite.children.get('deep');
+      expect(cft.lookup(FILE, ['suite', 'innerSuite', 'deep'])).to.equal(deep);
+    });
+
+    it('returns undefined when no path segment matches at all', () => {
+      const { cft } = buildTree();
+      expect(cft.lookup(FILE, ['nonExistent'])).to.be.undefined;
+    });
+
+    it('falls back to the deepest matched ancestor for an unresolvable tail', () => {
+      const { cft, suite } = buildTree();
+      expect(cft.lookup(FILE, ['suite', 'dynamicTest'])).to.equal(suite);
+    });
+
+    it('falls back to the deepest match when multiple trailing segments are missing', () => {
+      const { cft, suite } = buildTree();
+      expect(cft.lookup(FILE, ['suite', 'dynamic', 'nested'])).to.equal(suite);
+    });
+
+    it('falls back several levels deep when the leaf is missing', () => {
+      const { cft, innerSuite } = buildTree();
+      expect(cft.lookup(FILE, ['suite', 'innerSuite', 'missingLeaf'])).to.equal(innerSuite);
+    });
+
+    it('returns the suite when a hook path is encountered', () => {
+      const { cft, suite } = buildTree();
+      expect(cft.lookup(FILE, ['suite', '"before all" hook'])).to.equal(suite);
+    });
+
+    it('returns the suite for "after each" hooks', () => {
+      const { cft, suite } = buildTree();
+      expect(cft.lookup(FILE, ['suite', '"after each" hook for test1'])).to.equal(suite);
+    });
+
+    it('looks up across all files when no file hint is provided', () => {
+      const { cft, test2 } = buildTree();
+      expect(cft.lookup(undefined, ['suite', 'test2'])).to.equal(test2);
+    });
+
+    it('returns undefined when the file hint does not match any registered file', () => {
+      const { cft } = buildTree();
+      expect(cft.lookup('/other/file.js', ['suite', 'test1'])).to.be.undefined;
+    });
+
+    it('returns the file-level item when path is empty', () => {
+      const { cft, fileItem } = buildTree();
+      expect(cft.lookup(FILE, [])).to.equal(fileItem);
+    });
+  });
+});