Automation of Checkbox not working

[Jennifer Rothman]

I have this automation set up:

when custom field "Ran" is checked in a card with custom field "Repeat Type" set to "Daily", set date custom field "Next Run" to tomorrow at 5:00 am, and uncheck custom field "Ran"

When 'Ran' is checked, the 'Next Run' field is filled out correctly, but the field isn't unchecked. I have messed around with it, and determined that no automation involving changing the value of a checkbox custom field works. Is this a known bug? Is there something I am doing wrong?

[Jennifer Rothman]

I was messing around with it more, and it unchecked itself once, but I haven't been able to recreate the success since. It seems inconsistent at the very least, which isn't great for my use case.