diff --git a/CHANGES/1101.bugfix b/CHANGES/1101.bugfix
new file mode 100644
index 00000000..0bfcf6d5
--- /dev/null
+++ b/CHANGES/1101.bugfix
@@ -0,0 +1 @@
+Fixed edge case where metadata file did not match wheel metadata.
diff --git a/pulp_python/app/utils.py b/pulp_python/app/utils.py
index b66edb97..14385092 100644
--- a/pulp_python/app/utils.py
+++ b/pulp_python/app/utils.py
@@ -220,9 +220,12 @@ def extract_wheel_metadata(filename: str) -> bytes | None:
         return None
     try:
         with zipfile.ZipFile(filename, "r") as f:
-            for file_path in f.namelist():
-                if file_path.endswith(".dist-info/METADATA"):
-                    return f.read(file_path)
+            metadata_paths = [p for p in f.namelist() if p.endswith("METADATA")]
+            sorted_paths = sorted(metadata_paths, key=lambda s: s.count("/"))
+            for metadata_path in sorted_paths:
+                file = f.read(metadata_path)
+                if b"Metadata-Version" in file:
+                    return file
     except (zipfile.BadZipFile, KeyError, OSError) as e:
         log.warning(f"Failed to extract metadata file from {filename}: {e}")
     return None
diff --git a/pulp_python/tests/functional/api/test_crud_content_unit.py b/pulp_python/tests/functional/api/test_crud_content_unit.py
index 2aac0a98..3abf8fa7 100644
--- a/pulp_python/tests/functional/api/test_crud_content_unit.py
+++ b/pulp_python/tests/functional/api/test_crud_content_unit.py
@@ -200,4 +200,6 @@ def test_package_creation_with_metadata(
     distro = python_distribution_factory(repository=python_repo)
 
     # Test that metadata is accessible
-    ensure_metadata(pulp_content_url, distro.base_path, PYTHON_WHEEL_FILENAME)
+    ensure_metadata(
+        pulp_content_url, distro.base_path, PYTHON_WHEEL_FILENAME, "shelf-reader", "0.1"
+    )
diff --git a/pulp_python/tests/functional/api/test_pypi_apis.py b/pulp_python/tests/functional/api/test_pypi_apis.py
index ce1eced7..35d269ad 100644
--- a/pulp_python/tests/functional/api/test_pypi_apis.py
+++ b/pulp_python/tests/functional/api/test_pypi_apis.py
@@ -165,7 +165,9 @@ def test_package_upload_with_metadata(
     assert summary.added["python.python"]["count"] == 1
 
     # Test that metadata is accessible
-    ensure_metadata(pulp_content_url, distro.base_path, PYTHON_WHEEL_FILENAME)
+    ensure_metadata(
+        pulp_content_url, distro.base_path, PYTHON_WHEEL_FILENAME, "shelf-reader", "0.1"
+    )
 
 
 @pytest.mark.parallel
diff --git a/pulp_python/tests/functional/api/test_sync.py b/pulp_python/tests/functional/api/test_sync.py
index 5b19ae6b..a11806a5 100644
--- a/pulp_python/tests/functional/api/test_sync.py
+++ b/pulp_python/tests/functional/api/test_sync.py
@@ -354,4 +354,6 @@ def test_package_sync_with_metadata(
     distro = python_distribution_factory(repository=repo)
 
     # Test that metadata is accessible
-    ensure_metadata(pulp_content_url, distro.base_path, "pytz-2023.2-py2.py3-none-any.whl")
+    ensure_metadata(
+        pulp_content_url, distro.base_path, "pytz-2023.2-py2.py3-none-any.whl", "pytz", "2023.2"
+    )
diff --git a/pulp_python/tests/functional/api/test_upload.py b/pulp_python/tests/functional/api/test_upload.py
index 5d2e207e..43c65cdf 100644
--- a/pulp_python/tests/functional/api/test_upload.py
+++ b/pulp_python/tests/functional/api/test_upload.py
@@ -3,6 +3,7 @@
 from pulp_python.tests.functional.constants import (
     PYTHON_EGG_FILENAME,
     PYTHON_EGG_URL,
+    PYTHON_FIXTURES_URL,
     PYTHON_WHEEL_FILENAME,
     PYTHON_WHEEL_URL,
     PYTHON_EGG_SHA256,
@@ -61,7 +62,9 @@ def test_synchronous_package_upload_with_metadata(
     """
     Test that the synchronous upload of a Python wheel package creates a metadata artifact.
     """
-    python_file = download_python_file(PYTHON_WHEEL_FILENAME, PYTHON_WHEEL_URL)
+    wheel_filename = "setuptools-80.9.0-py3-none-any.whl"
+    wheel_url = urljoin(urljoin(PYTHON_FIXTURES_URL, "packages/"), wheel_filename)
+    python_file = download_python_file(wheel_filename, wheel_url)
     content_body = {"file": python_file}
     content = python_bindings.ContentPackagesApi.upload(**content_body)
 
@@ -70,7 +73,7 @@ def test_synchronous_package_upload_with_metadata(
     distro = python_distribution_factory(repository=python_repo)
 
     # Test that metadata is accessible
-    ensure_metadata(pulp_content_url, distro.base_path, PYTHON_WHEEL_FILENAME)
+    ensure_metadata(pulp_content_url, distro.base_path, wheel_filename, "setuptools", "80.9.0")
 
 
 @pytest.mark.parallel
diff --git a/pulp_python/tests/functional/utils.py b/pulp_python/tests/functional/utils.py
index b47215aa..9d672b80 100644
--- a/pulp_python/tests/functional/utils.py
+++ b/pulp_python/tests/functional/utils.py
@@ -123,7 +123,7 @@ def explore_links(page_url, page_name, links_found, msgs):
     return len(msgs) == 0, msgs
 
 
-def ensure_metadata(pulp_content_url, distro_base_path, filename):
+def ensure_metadata(pulp_content_url, distro_base_path, filename, name, version):
     """
     Tests that metadata is accessible for a given wheel package filename.
     """
@@ -132,4 +132,5 @@ def ensure_metadata(pulp_content_url, distro_base_path, filename):
     metadata_response = requests.get(metadata_url)
     assert metadata_response.status_code == 200
     assert len(metadata_response.content) > 0
-    assert "Name: " in metadata_response.text
+    assert f"Name: {name}" in metadata_response.text
+    assert f"Version: {version}" in metadata_response.text