diff --git a/CHANGES/682.bugfix b/CHANGES/682.bugfix
new file mode 100644
index 00000000..4bf3e5b5
--- /dev/null
+++ b/CHANGES/682.bugfix
@@ -0,0 +1 @@
+Fixed uploads not supporting packages using metadata spec 2.3
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 2f385f3c..25834bc2 100644
--- a/pulp_python/tests/functional/api/test_crud_content_unit.py
+++ b/pulp_python/tests/functional/api/test_crud_content_unit.py
@@ -1,5 +1,6 @@
 # coding=utf-8
 """Tests that perform actions over content unit."""
+import pytest
 from pulp_smash.pulp3.bindings import delete_orphans, monitor_task, PulpTaskError
 
 from pulp_python.tests.functional.utils import (
@@ -12,6 +13,7 @@
 from pulp_python.tests.functional.utils import set_up_module as setUpModule  # noqa:F401
 from tempfile import NamedTemporaryFile
 from urllib.parse import urljoin
+from pypi_simple import PyPISimple
 
 from pulp_smash.utils import http_get
 from pulp_python.tests.functional.constants import (
@@ -227,3 +229,16 @@ def check_package_data(self, content_unit, expected=PYTHON_PACKAGE_DATA):
         for k, v in expected.items():
             with self.subTest(key=k):
                 self.assertEqual(content_unit[k], v)
+
+
+@pytest.mark.parallel
+def test_upload_metadata_23_spec(python_content_factory):
+    """Test that packages using metadata spec 2.3 can be uploaded to pulp."""
+    filename = "urllib3-2.2.2-py3-none-any.whl"
+    with PyPISimple() as client:
+        page = client.get_project_page("urllib3")
+        for package in page.packages:
+            if package.filename == filename:
+                content = python_content_factory(filename, url=package.url)
+                assert content.metadata_version == "2.3"
+                break
diff --git a/pulp_python/tests/functional/conftest.py b/pulp_python/tests/functional/conftest.py
index 408f46a9..44c2886f 100644
--- a/pulp_python/tests/functional/conftest.py
+++ b/pulp_python/tests/functional/conftest.py
@@ -2,6 +2,7 @@
 import uuid
 
 from pulp_smash.pulp3.utils import gen_distribution, gen_repo
+from pulp_python.tests.functional.constants import PYTHON_EGG_FILENAME, PYTHON_URL
 from pulp_python.tests.functional.utils import gen_python_remote
 
 from pulpcore.client.pulp_python import (
@@ -130,6 +131,38 @@ def _gen_python_repo_sync(remote=None, mirror=False, repository=None, **body):
     yield _gen_python_repo_sync
 
 
+@pytest.fixture
+def download_python_file(tmp_path, http_get):
+    """Download a Python file and return its path."""
+    def _download_python_file(relative_path, url):
+        file_path = tmp_path / relative_path
+        with open(file_path, mode="wb") as f:
+            f.write(http_get(url))
+        return file_path
+
+    yield _download_python_file
+
+
+@pytest.fixture
+def python_content_factory(python_content_api_client, download_python_file, monitor_task):
+    """A factory to create a Python Package Content."""
+    def _gen_python_content(relative_path=PYTHON_EGG_FILENAME, url=None, **body):
+        body["relative_path"] = relative_path
+        if url:
+            body["file"] = download_python_file(relative_path, url)
+        elif not any(x in body for x in ("artifact", "file", "upload")):
+            body["file"] = download_python_file(PYTHON_EGG_FILENAME, PYTHON_URL)
+        if repo := body.get("repository"):
+            repo_href = repo if isinstance(repo, str) else repo.pulp_href
+            body["repository"] = repo_href
+
+        task = python_content_api_client.create(**body).task
+        response = monitor_task(task)
+        return python_content_api_client.read(response.created_resources[0])
+
+    yield _gen_python_content
+
+
 @pytest.fixture
 def python_content_summary(python_repo_api_client, python_repo_version_api_client):
     """Get a summary of the repository version's content."""
diff --git a/requirements.txt b/requirements.txt
index f1271e41..17c293c7 100644
--- a/requirements.txt
+++ b/requirements.txt
@@ -1,4 +1,6 @@
 pulpcore>=3.28.0,<3.40
-pkginfo>=1.8.2,<1.9.7
+pkginfo>=1.10.0,<1.12.0  # Twine has <1.11 in their requirements
 bandersnatch>=6.1,<6.2
 pypi-simple>=0.9.0,<1.0.0
+# pinned until https://github.com/Azure/Azurite/issues/2562 is resolved
+azure-storage-blob<12.26.0