Hello TJ,
Thank you for sharing the details and screenshots, this behavior is due to a recent change in Outlook on the web. When multiple calendars are selected, the default view is now Split view (each calendar in its own column). The good news is that the overlay/merged view is still available; it just needs to be toggled back on. If you're using New Outlook or Outlook Web:
- Go to Calendar.
- On the top toolbar, select View > Split View.
If you're using Classic Outlook:
- Go to Calendar.
- Choose View > (three dots) > Overlay.
- Click "<-" from right calendar (in the heading of each calendar) to merge it with left calendar.
Let me know if you need further guidance.
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Best regards.