Thank you for sharing details about the test step configurations and the misbehavior.
I noticed that you currently handle the download dialog with "CANCEL" action and the file will not be downloaded. That said, if you wanted to save the file, you need to provide the full path and file name in the "DownloadPath". You need to adjust the step properties and see if that will help with the test execution.
As for the file upload dialog that you have recorded in your test, you also need to have the full path and name of the file. Set it in the "FileUploadPath" for that step and run the test again.
In case you continue to experience any troubles, please clear/enable the application log and share it zipped along with the the .tstest file of this test, located in project root folder. I will analyze those resources and provide further assistance.
Thank you for your understanding and cooperation.