diff --git a/oras/provider.py b/oras/provider.py
index d53f61f..10a68fa 100644
--- a/oras/provider.py
+++ b/oras/provider.py
@@ -598,6 +598,7 @@ def chunked_upload(
         """
         # Start an upload session
         headers = {"Content-Type": "application/octet-stream", "Content-Length": "0"}
+        headers.update(self.headers)
 
         upload_url = f"{self.prefix}://{container.upload_blob_url()}"
         r = self.do_request(upload_url, "POST", headers=headers)
@@ -611,11 +612,6 @@ def chunked_upload(
         start = 0
         with open(blob, "rb") as fd:
             for chunk in oras.utils.read_in_chunks(fd, chunk_size=chunk_size):
-                print("uploading chunk starting at " + str(start))
-
-                if not chunk:
-                    break
-
                 end = start + len(chunk) - 1
                 content_range = "%s-%s" % (start, end)
                 headers = {
@@ -623,13 +619,19 @@ def chunked_upload(
                     "Content-Length": str(len(chunk)),
                     "Content-Type": "application/octet-stream",
                 }
+                headers.update(self.headers)
 
                 # Important to update with auth token if acquired
                 # TODO call to auth here
                 start = end + 1
                 self._check_200_response(
-                    self.do_request(session_url, "PATCH", data=chunk, headers=headers)
+                    r := self.do_request(
+                        session_url, "PATCH", data=chunk, headers=headers
+                    )
                 )
+                session_url = self._get_location(r, container)
+                if not session_url:
+                    raise ValueError(f"Issue retrieving session url: {r.json()}")
 
         # Finally, issue a PUT request to close blob
         session_url = oras.utils.append_url_params(
diff --git a/oras/tests/test_provider.py b/oras/tests/test_provider.py
index 2babd5a..7652ae0 100644
--- a/oras/tests/test_provider.py
+++ b/oras/tests/test_provider.py
@@ -3,6 +3,8 @@
 __license__ = "Apache-2.0"
 
 import os
+import platform
+import subprocess
 from pathlib import Path
 
 import pytest
@@ -13,7 +15,8 @@
 import oras.provider
 import oras.utils
 
-here = os.path.abspath(os.path.dirname(__file__))
+here = Path(__file__).resolve().parent
+OS_GB = "g" if platform.uname()[0].lower() == "darwin" else "G"
 
 
 @pytest.mark.with_auth(False)
@@ -62,6 +65,55 @@ def test_annotated_registry_push(tmp_path, registry, credentials, target):
         )
 
 
+@pytest.mark.with_auth(False)
+def test_chunked_push(tmp_path, registry, credentials, target):
+    """
+    Basic tests for oras chunked push
+    """
+    # Direct access to registry functions
+    client = oras.client.OrasClient(hostname=registry, insecure=True)
+    artifact = os.path.join(here, "artifact.txt")
+
+    assert os.path.exists(artifact)
+
+    res = client.push(files=[artifact], target=target, do_chunked=True)
+    assert res.status_code in [200, 201, 202]
+
+    files = client.pull(target, outdir=tmp_path)
+    assert str(tmp_path / "artifact.txt") in files
+    assert oras.utils.get_file_hash(artifact) == oras.utils.get_file_hash(files[0])
+
+    # large file upload
+    tmp_chunked = here / "chunked"
+    try:
+        subprocess.run(
+            [
+                "dd",
+                "if=/dev/null",
+                f"of={tmp_chunked}",
+                "bs=1",
+                "count=0",
+                f"seek=15{OS_GB}",
+            ],
+        )
+
+        res = client.push(files=[tmp_chunked], target=target, do_chunked=True)
+        assert res.status_code in [200, 201, 202]
+
+        files = client.pull(target, outdir=tmp_path / "download")
+        download = str(tmp_path / "download/chunked")
+        assert download in files
+        assert oras.utils.get_file_hash(str(tmp_chunked)) == oras.utils.get_file_hash(
+            download
+        )
+    finally:
+        tmp_chunked.unlink()
+
+    # File that doesn't exist
+    with pytest.raises(FileNotFoundError):
+        res = client.push(files=[tmp_path / "none"], target=target)
+
+
 def test_parse_manifest(registry):
     """
     Test parse manifest function.