diff --git a/roboflow/core/workspace.py b/roboflow/core/workspace.py
index de5fcca4..73ed1244 100644
--- a/roboflow/core/workspace.py
+++ b/roboflow/core/workspace.py
@@ -86,10 +86,11 @@ def project(self, project_id):
         if self.__api_key in DEMO_KEYS:
             return Project(self.__api_key, {}, self.model_format)
 
-        # project_id = project_id.replace(self.url + "/", "")
+        if not project_id:
+            raise RuntimeError("Project id is required but none was specified.")
 
         if "/" in project_id:
-            raise RuntimeError(f"The {project_id} project is not available in this ({self.url}) workspace")
+            raise RuntimeError(f"{project_id=} cannot contain a '/', use workspace argument to change the URL.")
 
         dataset_info = rfapi.get_project(self.__api_key, self.url, project_id)
         dataset_info = dataset_info["project"]
diff --git a/roboflow/roboflowpy.py b/roboflow/roboflowpy.py
index 70cf6db9..9922753c 100755
--- a/roboflow/roboflowpy.py
+++ b/roboflow/roboflowpy.py
@@ -72,16 +72,18 @@ def upload_image(args):
     rf = roboflow.Roboflow()
     workspace = rf.workspace(args.workspace)
     project = workspace.project(args.project)
-    project.single_upload(
-        image_path=args.imagefile,
-        annotation_path=args.annotation,
-        annotation_labelmap=args.labelmap,
-        split=args.split,
-        num_retry_uploads=args.num_retries,
-        batch_name=args.batch,
-        tag_names=args.tag_names.split(",") if args.tag_names else [],
-        is_prediction=args.is_prediction,
-    )
+    tag_names = args.tag_names.split(",") if args.tag_names else []
+    for image_path in args.imagefile:
+        project.single_upload(
+            image_path=image_path,
+            annotation_path=args.annotation,
+            annotation_labelmap=args.labelmap,
+            split=args.split,
+            num_retry_uploads=args.num_retries,
+            batch_name=args.batch,
+            tag_names=tag_names,
+            is_prediction=args.is_prediction,
+        )
 
 
 def upload_model(args):
@@ -263,10 +265,11 @@ def _add_download_parser(subparsers):
 
 
 def _add_upload_parser(subparsers):
-    upload_parser = subparsers.add_parser("upload", help="Upload a single image to a dataset")
+    upload_parser = subparsers.add_parser("upload", help="Upload one or more images to a dataset")
     upload_parser.add_argument(
         "imagefile",
-        help="path to image file",
+        nargs="+",
+        help="path to one or more image files to upload",
     )
     upload_parser.add_argument(
         "-w",
@@ -276,7 +279,8 @@ def _add_upload_parser(subparsers):
     upload_parser.add_argument(
         "-p",
         dest="project",
-        help="project_id to upload the image into",
+        required=True,
+        help="project_id to upload the image into (required)",
     )
     upload_parser.add_argument(
         "-a",