diff --git a/roboflow/core/project.py b/roboflow/core/project.py
index 79f01152..34f01475 100644
--- a/roboflow/core/project.py
+++ b/roboflow/core/project.py
@@ -1,6 +1,7 @@
 import datetime
 import json
 import os
+import re
 import sys
 import time
 import warnings
@@ -493,6 +494,8 @@ def single_upload(
                 )
                 image_id = uploaded_image["id"]
                 upload_retry_attempts = retry.retries
+            except rfapi.UploadError as e:
+                raise RuntimeError(f"Error uploading image: {self._parse_upload_error(e)}")
             except BaseException as e:
                 uploaded_image = {"error": e}
             finally:
@@ -514,6 +517,8 @@ def single_upload(
                     annotation_labelmap=annotation_labelmap,
                     overwrite=annotation_overwrite,
                 )
+            except rfapi.UploadError as e:
+                raise RuntimeError(f"Error uploading annotation: {self._parse_upload_error(e)}")
             except BaseException as e:
                 uploaded_annotation = {"error": e}
             finally:
@@ -546,6 +551,20 @@ def _annotation_params(self, annotation_path):
             )
         return annotation_name, annotation_string
 
+    def _parse_upload_error(self, error: rfapi.UploadError) -> str:
+        dict_part = str(error).split(": ", 2)[2]
+        dict_part = dict_part.replace("True", "true")
+        dict_part = dict_part.replace("False", "false")
+        dict_part = dict_part.replace("None", "null")
+        if re.search(r"'\w+':", dict_part):
+            temp_str = dict_part.replace(r"\'", "<PLACEHOLDER>")
+            temp_str = temp_str.replace('"', r"\"")
+            temp_str = temp_str.replace("'", '"')
+            dict_part = temp_str.replace("<PLACEHOLDER>", "'")
+        parsed_dict: dict = json.loads(dict_part)
+        message = parsed_dict.get("message")
+        return message or str(parsed_dict)
+
     def search(
         self,
         like_image: str = None,