diff --git a/README.md b/README.md
index 0222bf5..d4c1bdc 100644
--- a/README.md
+++ b/README.md
@@ -57,7 +57,15 @@ Every `markdawn` file under the `tests` directory that already contains mark hea
 <your-content>
 ```
 
-The directive is only valid for the specified directory, in the example above files places under `tests/integration/` will not have the headers appended.
+The directive supports glob matching and prioritize the longest directory first, for example:
+
+```yaml
+default_headers: |
+  tests/**=FOO->Tests
+  tests/resources/**=FOO->Tests->Resources
+```
+
+Files under `tests/resources/` will have `FOO->Tests->Resources` as headers, while files under `tests/other-dir` will have `FOO->Tests`.
 
 ## Example workflow
 
diff --git a/mark2confluence/main.py b/mark2confluence/main.py
index 530af26..bfc05e8 100755
--- a/mark2confluence/main.py
+++ b/mark2confluence/main.py
@@ -4,6 +4,7 @@
 import re
 import subprocess
 from datetime import datetime,timedelta
+from fnmatch import fnmatch
 from typing import List, Tuple
 import jinja2
 from loguru import logger
@@ -194,6 +195,13 @@ def get_header(self) -> str:
       header += f"<!-- Parent: {parent} -->\n"
     return header
 
+  def is_directory_included(self, directory: str) -> bool:
+    global cfg
+    sanitized_dir = directory.replace(f"{cfg.github.WORKSPACE}/", "")
+    if not sanitized_dir.endswith("/"):
+      sanitized_dir += "/"
+    return fnmatch(sanitized_dir, self.directory)
+
 def _parse_parent_string(parent_string: str) -> Tuple[str, str, List[str]]:
   dir_separator = "="
   spaces_separator = "->"
@@ -223,20 +231,21 @@ def get_default_parents(parents_string: str) -> List[ParentCfg]:
   for parent_string in parents_string.split("\n"):
     directory, space, parents = _parse_parent_string(parent_string)
     default_parents.append(ParentCfg(directory, space, parents))
+  default_parents.sort(key=lambda cfg: len(cfg.directory), reverse=True)
   return default_parents
 
 def inject_default_parents(path: str, default_parents_cfg: List[ParentCfg]):
   global cfg
-  file_dir = f"{os.path.dirname(os.path.relpath(path))}/"
+  file_dir = f"{os.path.dirname(os.path.abspath(path))}"
   for parent_cfg in default_parents_cfg:
-    cfg_abs_dir = f"{cfg.github.WORKSPACE}/{parent_cfg.directory}"
-    if os.path.isdir(cfg_abs_dir) and os.path.samefile(file_dir, cfg_abs_dir):
+    if parent_cfg.is_directory_included(file_dir):
       header = parent_cfg.get_header()
       with open(path, 'r') as f:
         file_content = f.read()
       file_content = f"{header}{file_content}"
       with open(path, "w") as f:
         f.write(file_content)
+      return
 
 
 def main()->int:
diff --git a/tests/test_main.py b/tests/test_main.py
index 9bd389c..d656e0a 100644
--- a/tests/test_main.py
+++ b/tests/test_main.py
@@ -1,10 +1,12 @@
 import os
 import pytest
 import shutil
+from supermutes import dot
 
 import mark2confluence.main as main
 
 RESOURCE_DIR = f"{os.path.dirname(os.path.abspath(__file__))}/resources"
+WORKSPACE = os.path.realpath(f"{os.path.dirname(os.path.abspath(__file__))}/..")
 
 def clean_github_environment_variables():
     if(os.getenv("CI", False)):
@@ -121,17 +123,24 @@ def test_get_default_parents(string, expected_parents_count):
 def test_ParentCfg_get_header(cfg: main.ParentCfg, expected_header):
     assert cfg.get_header() == expected_header
 
-def test_inject_default_parents():
+def test_inject_default_parents(monkeypatch):
+    monkeypatch.setattr('mark2confluence.main.cfg', dot.dotify({"github": {"WORKSPACE": WORKSPACE}}))
+
     base_dir = f"{RESOURCE_DIR}/markdown/test_inject_default_parents"
     source_file_path = f"{base_dir}/0-input.md"
     expected_file_path = f"{base_dir}/0-output.md"
-    parsed_file_path = "tests/parsed_file.md"
+    parsed_file_dir = f"{WORKSPACE}/tests/foo"
+    parsed_file_path = f"{parsed_file_dir}/parsed_file.md"
     cfgs = [
-        main.ParentCfg(directory="tests/", space="FOO", parents=["BAR"]),
+        main.ParentCfg(directory="tests/foo/bar", space="FOO", parents=["BAZ"]),
+        main.ParentCfg(directory="tests/foo/*", space="FOO", parents=["BAR"]),
+        main.ParentCfg(directory="tests/*", space="FOO", parents=["BAZ"]),
         main.ParentCfg(directory="mark2confluence/", space="BOZ", parents=["BIZ"]),
     ]
 
+    os.makedirs(parsed_file_dir, exist_ok=True)
     shutil.copy(source_file_path, parsed_file_path)
+
     main.inject_default_parents(parsed_file_path, cfgs)
 
     with open(parsed_file_path, "r") as f:
@@ -142,4 +151,4 @@ def test_inject_default_parents():
     try:
         assert parsed_file_content == expected_file_content
     finally:
-        os.remove(parsed_file_path)
+        shutil.rmtree(parsed_file_dir)