Good evening Brenden and welcome back!
Thank you for reaching out to us.
We are sorry to hear about the calendar view not working as you expect it to.
I would love to help you with this topic.
This is a bug that affects only the monthly view on certain installs.
What is going on is that on a single day, events get sorted by post ID instead of the time (hence the apparent randomness of the sorting).
We apologize for the inconvenience this might have caused.
Unfortunately, I cannot commit to a release date for a fix at this point. But you will be contacted as soon as there is one so stay tuned.
In the meantime, if you don’t mind, I would be curious to see if reordering the posts from a specific day in the correct sequence using a plugin such as this one: https://wordpress.org/plugins/intuitive-custom-post-order/ would work as a temporary workaround ?
I wish I had a better answer for you, but for now it’s the best one I have.
Best regards,
Geoff B.