I don't know anything about the Connect server, but when I upload to a cloud based LMS I publish to a .zip file and upload the .zip. Have you tried that at all?
Thanks for the suggestion, that worked! Now I get the full experience.
Just some info as to what is happening.
Whenever you are uploading your pptx to connect, Presenter's assets folder do not get uploaded to connect
In order to publish the conent like audio, video, attachments to connect, you will have to use the publish to connect feature in Presenter.
Else you can publish to tour local machine and then upload the zip as content to connect.
Hope this resolves your issue
Thank you Mahesh, that solved the problem!