@Thebigred Sure, just wanted to check you’d caught up on those threads first. Looking at your direct concerns:
Have you loaded up your current plan into the Calendar? This should load up all the rides that are in your plan (past and future dates) and then map your completed rides against the scheduled plan rides. If you haven’t done this, that’s the first step. If you are having problems doing it, just released today is a more comprehensive help section Calendar Updates: Copy Week, Collapse Training Stress Graph, Help Box. If you’re still having trouble, I’d shoot a note to support@trainerroad.com
The easiest place to make edits to the Calendar is the online version, so I would recommend trying to do this there. You should be able to drag the planned workout (from Oct 2) onto yesterdays date. This should auto-associate the completed workout with the planned one, if it doesn’t click into the completed one and use the Associate function.
Do the steps above, I suspect this may solve your problem. I see you said that you deleted it, so you won’t have a planned workout to associate it with. You could just add it back in to test out the Associate feature.
This is interim Mac functionality so that you can see your next ride and initiate the workout in-app. TR worked really hard after the Calendar feature was released to make this possible after use feedback. It is expected that full Calendar functionality will become available in the future.