As far as I can see, the system at present is not only forgetting when it last optimized the drives, it's also misidentifying them when it comes to automatically optimizing them, even though they appear to be identified correctly in the list of drives.
That's why it's trying to TRIM conventional HDDs, which isn't possible, and throwing error messages into the event log as a result.
The opposite scenario, trying to defragment SSDs, is unfortunately very possible, and it could well be doing this, which is not good!
I fear that the automatic optimization and the manual optimization are behaving differently, and the manual option is behaving correctly, the automatic isn't.