Welcome to the community, @Thomas_Chiginsky! :grinning_face_with_big_eyes: Could you provide more details on the field types for each of the fields that you’re referring to? I can’t tell which are date fields and which may be formulas. If you do have formulas, please list what those are in full.
My gut feeling is this: if you’re sorting/grouping based on a formatted date—i.e. a formula that outputs a display-friendly date in “MMMM DD, YYYY” format—then that might explain the odd order. That formatted date is no longer a date. It’s a string of characters, so sorting/grouping will work alphabetically based on the first character in the string.