diff --git a/src/cli/onefuzz/azcopy.py b/src/cli/onefuzz/azcopy.py
index ac2b706d2..8b91d0cba 100644
--- a/src/cli/onefuzz/azcopy.py
+++ b/src/cli/onefuzz/azcopy.py
@@ -21,9 +21,18 @@ def find_azcopy() -> str:
 
 
 def azcopy_sync(src: str, dst: str) -> None:
-    """Expose azcopy for uploading/downloading files"""
+    """Expose azcopy for syncing existing files"""
 
     azcopy = find_azcopy()
 
     # security note: callers need to understand the src/dst for this.
     subprocess.check_output([azcopy, "sync", src, dst, "--recursive=true"])  # nosec
+
+
+def azcopy_copy(src: str, dst: str) -> None:
+    """Expose azcopy for uploading/downloading files"""
+
+    azcopy = find_azcopy()
+
+    # security note: callers need to understand the src/dst for this.
+    subprocess.check_output([azcopy, "cp", src, dst, "--recursive=true"])  # nosec
diff --git a/src/cli/onefuzz/backend.py b/src/cli/onefuzz/backend.py
index 8f33a8ef1..3376da3dd 100644
--- a/src/cli/onefuzz/backend.py
+++ b/src/cli/onefuzz/backend.py
@@ -9,6 +9,7 @@ import json
 import logging
 import os
 import sys
+import tempfile
 import time
 from dataclasses import asdict, is_dataclass
 from enum import Enum
@@ -36,7 +37,7 @@ from tenacity.retry import retry_if_exception_type
 from tenacity.stop import stop_after_attempt
 from tenacity.wait import wait_random
 
-from .azcopy import azcopy_sync
+from .azcopy import azcopy_copy, azcopy_sync
 
 _ACCESSTOKENCACHE_UMASK = 0o077
 
@@ -364,16 +365,36 @@ class ContainerWrapper:
         reraise=True,
     )
     def upload_file(self, file_path: str, blob_name: str) -> None:
-        with open(file_path, "rb") as handle:
-            self.client.upload_blob(
-                name=blob_name, data=handle, overwrite=True, max_concurrency=10
+        try:
+            # Split the container URL to insert the blob_name
+            url_parts = self.container_url.split("?", 1)
+
+            # Default to azcopy if it is installed
+            azcopy_copy(file_path, url_parts[0] + "/" + blob_name + "?" + url_parts[1])
+        except Exception as exc:
+            # A subprocess exception would typically only contain the exit status.
+            LOGGER.warning(
+                "Upload using azcopy failed. Check the azcopy logs for more information."
             )
+            LOGGER.warning(exc)
+            # Indicate the switch in the approach for clarity in debugging
+            LOGGER.warning("Now attempting to upload using the Python SDK...")
+
+            # This does not have a try/except since it should be caught by the retry system.
+            # The retry system will always attempt azcopy first and this approach second
+            with open(file_path, "rb") as handle:
+                # Using the Azure SDK default max_concurrency
+                self.client.upload_blob(name=blob_name, data=handle, overwrite=True)
         return None
 
     def upload_file_data(self, data: str, blob_name: str) -> None:
-        self.client.upload_blob(
-            name=blob_name, data=data, overwrite=True, max_concurrency=10
-        )
+        with tempfile.TemporaryDirectory() as tmpdir:
+            filename = os.path.join(tmpdir, blob_name)
+
+            with open(filename, "w") as handle:
+                handle.write(data)
+
+            self.upload_file(filename, blob_name)
 
     def upload_dir(self, dir_path: str) -> None:
         # security note: the src for azcopy comes from the server which is