diff --git a/test/TestFilePathEvaluation.py b/test/TestFilePathEvaluation.py
new file mode 100644
index 00000000000..cb6cdebf311
--- /dev/null
+++ b/test/TestFilePathEvaluation.py
@@ -0,0 +1,128 @@
+"""Testing file path evaluation when using import_tasks / include_tasks."""
+import os
+import shutil
+import tempfile
+import textwrap
+
+import pytest
+
+from ansiblelint.runner import Runner
+
+LAYOUT_IMPORTS = {
+    'directories': ['tasks', 'tasks/subtasks'],
+    'files': {
+        'main.yml': textwrap.dedent(
+            """\
+            ---
+            - hosts: target
+              gather_facts: false
+              tasks:
+                - name: from main import task 1
+                  import_tasks: tasks/task_1.yml
+            """
+        ),
+        'tasks/task_1.yml': textwrap.dedent(
+            """\
+            ---
+            - name: from task 1 import task 2
+              import_tasks: tasks/task_2.yml
+            """
+        ),
+        'tasks/task_2.yml': textwrap.dedent(
+            """\
+            ---
+            - name: from task 2 import subtask 1
+              import_tasks: tasks/subtasks/subtask_1.yml
+            """
+        ),
+        'tasks/subtasks/subtask_1.yml': textwrap.dedent(
+            """\
+            ---
+            - name: from subtask 1 import subtask 2
+              import_tasks: tasks/subtasks/subtask_2.yml
+            """
+        ),
+        'tasks/subtasks/subtask_2.yml': textwrap.dedent(
+            """\
+            ---
+            - name: from subtask 2 do something
+              debug:
+                msg: |
+                  Something...
+            """
+        ),
+    },
+}
+
+LAYOUT_INCLUDES = {
+    'directories': ['tasks', 'tasks/subtasks'],
+    'files': {
+        'main.yml': textwrap.dedent(
+            """\
+            ---
+            - hosts: target
+              gather_facts: false
+              tasks:
+                - name: from main import task 1
+                  include_tasks: tasks/task_1.yml
+            """
+        ),
+        'tasks/task_1.yml': textwrap.dedent(
+            """\
+            ---
+            - name: from task 1 import task 2
+              include_tasks: tasks/task_2.yml
+            """
+        ),
+        'tasks/task_2.yml': textwrap.dedent(
+            """\
+            ---
+            - name: from task 2 import subtask 1
+              include_tasks: tasks/subtasks/subtask_1.yml
+            """
+        ),
+        'tasks/subtasks/subtask_1.yml': textwrap.dedent(
+            """\
+            ---
+            - name: from subtask 1 import subtask 2
+              include_tasks: tasks/subtasks/subtask_2.yml
+            """
+        ),
+        'tasks/subtasks/subtask_2.yml': textwrap.dedent(
+            """\
+            ---
+            - name: from subtask 2 do something
+              debug:
+                msg: |
+                  Something...
+            """
+        ),
+    },
+}
+
+
+@pytest.mark.parametrize(
+    'ansible_project_layout',
+    (
+        pytest.param(LAYOUT_IMPORTS, id='using only import_tasks'),
+        pytest.param(LAYOUT_INCLUDES, id='using only include_tasks'),
+    ),
+)
+@pytest.mark.xfail(
+    reason='https://github.com/ansible-community/ansible-lint/issues/1446'
+)
+def test_file_path_evaluation(default_rules_collection, ansible_project_layout):
+    """Test if the usage of import_tasks / include_tasks will end up with false positive load-failure due to incorrect file path evaluation."""
+    root_dir_path = tempfile.mkdtemp()
+
+    for directory in ansible_project_layout['directories']:
+        os.makedirs(os.path.join(root_dir_path, directory), exist_ok=True)
+
+    for file_path, file_content in ansible_project_layout['files'].items():
+        open(os.path.join(root_dir_path, file_path), 'w').write(file_content)
+
+    result = Runner(root_dir_path, rules=default_rules_collection).run()
+
+    shutil.rmtree(root_dir_path)
+
+    assert '[Errno 2] No such file or directory:' in result[0].message