diff --git a/tests/test_diagnostic_bundle.py b/tests/test_diagnostic_bundle.py
new file mode 100644
index 00000000..a6c4cf8b
--- /dev/null
+++ b/tests/test_diagnostic_bundle.py
@@ -0,0 +1,103 @@
+# Fix for Issue #1: [$25 BOUNTY] [Python] Add diagnostic bundle validation tests
+
+# tests/test_diagnostic_bundle.py
+import os
+import json
+import unittest
+from unittest.mock import patch
+from build import generate_diagnostic_bundle
+
+class TestDiagnosticBundle(unittest.TestCase):
+    def test_diagnostic_bundle_generation(self):
+        # Run the build script to generate the diagnostic bundle
+        generate_diagnostic_bundle()
+
+        # Get the list of files in the diagnostic directory
+        diagnostic_dir = 'diagnostic'
+        files = os.listdir(diagnostic_dir)
+
+        # Find the generated diagnostic bundle files
+        json_file = None
+        logd_file = None
+        for file in files:
+            if file.startswith('build-') and file.endswith('.json'):
+                json_file = os.path.join(diagnostic_dir, file)
+            elif file.startswith('build-') and file.endswith('.logd'):
+                logd_file = os.path.join(diagnostic_dir, file)
+
+        # Check that both files were generated
+        self.assertIsNotNone(json_file)
+        self.assertIsNotNone(logd_file)
+
+        # Check that the JSON file contains the expected metadata
+        with open(json_file, 'r') as f:
+            metadata = json.load(f)
+            self.assertTrue('repository_relative_paths' in metadata)
+            self.assertTrue('redacted_metadata' in metadata)
+
+        # Check that local home/repo/temp paths and usernames are redacted
+        self.assertNotIn('/home/', json.dumps(metadata))
+        self.assertNotIn('/repo/', json.dumps(metadata))
+        self.assertNotIn('/temp/', json.dumps(metadata))
+        self.assertNotIn('username', json.dumps(metadata))
+
+        # Check that the .logd file exists and is not empty
+        self.assertGreater(os.path.getsize(logd_file), 0)
+
+    def test_diagnostic_bundle_validation(self):
+        # Test that the diagnostic bundle validation fails when the JSON file is missing
+        with patch('os.listdir', return_value=['build-XXX.logd']):
+            with self.assertRaises(FileNotFoundError):
+                generate_diagnostic_bundle()
+
+        # Test that the diagnostic bundle validation fails when the .logd file is missing
+        with patch('os.listdir', return_value=['build-XXX.json']):
+            with self.assertRaises(FileNotFoundError):
+                generate_diagnostic_bundle()
+
+        # Test that the diagnostic bundle validation fails when the pair is mismatched
+        with patch('os.listdir', return_value=['build-XXX.json', 'build-YYY.logd']):
+            with self.assertRaises(ValueError):
+                generate_diagnostic_bundle()
+
+# build.py
+import os
+import json
+import subprocess
+
+def generate_diagnostic_bundle():
+    # Generate the diagnostic bundle
+    subprocess.run(['python3', 'build.py'])
+
+    # Get the list of files in the diagnostic directory
+    diagnostic_dir = 'diagnostic'
+    files = os.listdir(diagnostic_dir)
+
+    # Find the generated diagnostic bundle files
+    json_file = None
+    logd_file = None
+    for file in files:
+        if file.startswith('build-') and file.endswith('.json'):
+            json_file = os.path.join(diagnostic_dir, file)
+        elif file.startswith('build-') and file.endswith('.logd'):
+            logd_file = os.path.join(diagnostic_dir, file)
+
+    # Check that both files were generated
+    if json_file is None or logd_file is None:
+        raise FileNotFoundError('Diagnostic bundle files not found')
+
+    # Check that the pair is matched
+    if os.path.basename(json_file).split('.')[0] != os.path.basename(logd_file).split('.')[0]:
+        raise ValueError('Diagnostic bundle pair is mismatched')
+
+    # Check that the JSON file contains the expected metadata
+    with open(json_file, 'r') as f:
+        metadata = json.load(f)
+        if 'repository_relative_paths' not in metadata or 'redacted_metadata' not in metadata:
+            raise ValueError('Diagnostic bundle metadata is invalid')
+
+    # Check that local home/repo/temp paths and usernames are redacted
+    with open(json_file, 'r') as f:
+        metadata = json.load(f)
+        if '/home/' in json.dumps(metadata) or '/repo/' in json.dumps(metadata) or '/temp/' in json.dumps(metadata) or 'username' in json.dumps(metadata):
+            raise ValueError('Diagnostic bundle metadata is not redacted')
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