diff --git a/agbenchmark/Challenge.py b/agbenchmark/Challenge.py
index 9828a0e9..d159296b 100644
--- a/agbenchmark/Challenge.py
+++ b/agbenchmark/Challenge.py
@@ -1,5 +1,5 @@
 import os
-from typing import Optional
+import glob
 from agbenchmark.challenges.define_task_types import Ground
 
 
@@ -14,6 +14,26 @@ class Challenge:
         with open(workspace_dir, "r") as f:
             return f.read()
 
+    @staticmethod
+    def open_files(workspace: str, file_patterns: list):
+        script_dir = os.path.abspath(workspace)
+        files_contents = []
+
+        for file_pattern in file_patterns:
+            # Check if it is a file extension
+            if file_pattern.startswith("."):
+                # Find all files with the given extension in the workspace
+                matching_files = glob.glob(os.path.join(script_dir, "*" + file_pattern))
+            else:
+                # Otherwise, it is a specific file
+                matching_files = [os.path.join(script_dir, file_pattern)]
+
+            for file_path in matching_files:
+                with open(file_path, "r") as f:
+                    files_contents.append(f.read())
+
+        return files_contents
+
     @staticmethod
     def write_to_file(workspace: str, filename: str, content: str):
         script_dir = os.path.abspath(workspace)
diff --git a/agbenchmark/challenges/retrieval/r1/r1_test.py b/agbenchmark/challenges/retrieval/r1/r1_test.py
index 489d298f..2a7d92a7 100644
--- a/agbenchmark/challenges/retrieval/r1/r1_test.py
+++ b/agbenchmark/challenges/retrieval/r1/r1_test.py
@@ -23,10 +23,12 @@ class TestRetrieval1(RetrievalChallenge):
         indirect=True,
     )
     def test_retrieval(self, workspace, current_challenge_data):
-        file = self.open_file(workspace, data.ground.files[0])
+        files_contents = self.open_files(workspace, data.ground.files)
 
-        score = self.scoring(file, data.ground)
+        scores = []
+        for file_content in files_contents:
+            score = self.scoring(file_content, data.ground)
+            print("Your score is:", score)
+            scores.append(score)
 
-        print("You score is:", score)
-
-        assert score
+        assert 1 in scores
diff --git a/agbenchmark/tests/basic_abilities/read_file/read_file_test.py b/agbenchmark/tests/basic_abilities/read_file/read_file_test.py
index 7d14228c..90946670 100644
--- a/agbenchmark/tests/basic_abilities/read_file/read_file_test.py
+++ b/agbenchmark/tests/basic_abilities/read_file/read_file_test.py
@@ -32,10 +32,12 @@ class TestReadFile(BasicChallenge):
     )
     @pytest.mark.depends(on=data.dependencies)
     def test_read_file(self, workspace):
-        file = self.open_file(workspace, data.ground.files[0])
+        files_contents = self.open_files(workspace, data.ground.files)
 
-        score = self.scoring(file, data.ground)
+        scores = []
+        for file_content in files_contents:
+            score = self.scoring(file_content, data.ground)
+            print("Your score is:", score)
+            scores.append(score)
 
-        print("You score is:", score)
-
-        assert score
+        assert 1 in scores
diff --git a/agbenchmark/tests/basic_abilities/write_file/w_file_data.json b/agbenchmark/tests/basic_abilities/write_file/w_file_data.json
index 1d262108..037c5bd8 100644
--- a/agbenchmark/tests/basic_abilities/write_file/w_file_data.json
+++ b/agbenchmark/tests/basic_abilities/write_file/w_file_data.json
@@ -6,7 +6,7 @@
     "answer": "Washington",
     "should_contain": ["Washington"],
     "should_not_contain": ["New York", "Los Angeles", "San Francisco"],
-    "files": ["file_to_check.txt"]
+    "files": [".txt"]
   },
   "mock_func": "basic_write_file_mock",
   "info": {
diff --git a/agbenchmark/tests/basic_abilities/write_file/write_file_test.py b/agbenchmark/tests/basic_abilities/write_file/write_file_test.py
index 33012889..187378ff 100644
--- a/agbenchmark/tests/basic_abilities/write_file/write_file_test.py
+++ b/agbenchmark/tests/basic_abilities/write_file/write_file_test.py
@@ -23,10 +23,12 @@ class TestWriteFile(BasicChallenge):
     )
     @pytest.mark.depends(name="test_write_file")
     def test_write_file(self, workspace):
-        file = self.open_file(workspace, data.ground.files[0])
+        files_contents = self.open_files(workspace, data.ground.files)
 
-        score = self.scoring(file, data.ground)
+        scores = []
+        for file_content in files_contents:
+            score = self.scoring(file_content, data.ground)
+            print("Your score is:", score)
+            scores.append(score)
 
-        print("You score is:", score)
-
-        assert score
+        assert 1 in scores
diff --git a/agbenchmark/tests/regression/regression_tests.json b/agbenchmark/tests/regression/regression_tests.json
index 9e26dfee..c84fc9c9 100644
--- a/agbenchmark/tests/regression/regression_tests.json
+++ b/agbenchmark/tests/regression/regression_tests.json
@@ -1 +1,14 @@
-{}
\ No newline at end of file
+{
+    "TestWriteFile": {
+        "difficulty": "basic",
+        "dependencies": [],
+        "test": "agbenchmark/tests/basic_abilities/write_file/write_file_test.py::TestWriteFile::test_write_file[regression_data0-server_response0]"
+    },
+    "TestReadFile": {
+        "difficulty": "basic",
+        "dependencies": [
+            "test_write_file"
+        ],
+        "test": "agbenchmark/tests/basic_abilities/read_file/read_file_test.py::TestReadFile::test_read_file[regression_data0-server_response0]"
+    }
+}
\ No newline at end of file