The evaluation fails because $currentObject/Expiration_Date value is 'empty' in that specific case.
Add a check in the begging
if $currentObject/Expiration_Date != empty and $currentObject/Expiration_Date <= [%CurrentDateTime%] then ...
Or just make sure that everytime the grid is rendered the expiration_date is not empty
Check the access rights on Expiration_Date and add a != empty check in the expression
Hey Tyler, this looks frustrating dude. I hate these kinds of errors.
One thing you could try and do to debug is temporarily create an attribute in whatever entity the Expiration_Date attribute is located in and set the value of the new attribute to the current date time. After that change, change your expression to reference the new attribute and see if it gives you the same error. I think you may be on to something with your hunch, but I've never experienced something like this before.
Good luck!