diff --git a/plugins/DigitalLibrary/src/DFFileExportAndUploadManager.py b/plugins/DigitalLibrary/src/DFFileExportAndUploadManager.py
index 4defd2f409..26912abd9a 100644
--- a/plugins/DigitalLibrary/src/DFFileExportAndUploadManager.py
+++ b/plugins/DigitalLibrary/src/DFFileExportAndUploadManager.py
@@ -135,9 +135,21 @@ class DFFileExportAndUploadManager:
             file_name = file_upload_response.job_name if file_upload_response.job_name is not None else ""
         else:
             Logger.log("e", "Wrong response type received. Aborting uploading file to the Digital Library")
+            getBackwardsCompatibleMessage(
+                    text = "Upload error",
+                    title = f"Failed to upload {file_name}. Received unexpected response from server.",
+                    message_type_str = "ERROR",
+                    lifetime = 0
+            ).show()
             return
         if file_name not in self._file_upload_job_metadata:
             Logger.error(f"API response for uploading doesn't match the file name we just uploaded: {file_name} was never uploaded.")
+            getBackwardsCompatibleMessage(
+                    text = "Upload error",
+                    title = f"Failed to upload {file_name}. Name doesn't match the one sent back in confirmation.",
+                    message_type_str = "ERROR",
+                    lifetime = 0
+            ).show()
             return
         with self._message_lock:
             self.progress_message.show()
diff --git a/plugins/DigitalLibrary/src/DigitalFactoryController.py b/plugins/DigitalLibrary/src/DigitalFactoryController.py
index cee367e188..a64a0cee0f 100644
--- a/plugins/DigitalLibrary/src/DigitalFactoryController.py
+++ b/plugins/DigitalLibrary/src/DigitalFactoryController.py
@@ -501,6 +501,12 @@ class DigitalFactoryController(QObject):
         """
         if not download_url:
             Logger.log("e", "No download url for file '{}'".format(file_name))
+            getBackwardsCompatibleMessage(
+                    text = "Download error",
+                    title = f"No download url could be found for '{file_name}'.",
+                    message_type_str = "ERROR",
+                    lifetime = 0
+            ).show()
             return
 
         progress_message = Message(text = "{0}/{1}".format(project_name, file_name), dismissable = False, lifetime = 0,
@@ -584,6 +590,12 @@ class DigitalFactoryController(QObject):
         """
         if self._selected_project_idx == -1:
             Logger.log("e", "No DF Library project is selected.")
+            getBackwardsCompatibleMessage(
+                    text = "No Digital Library project was selected",
+                    title = "No project selected",
+                    message_type_str = "ERROR",
+                    lifetime = 0
+            ).show()
             return
 
         if filename == "":