In a few hours you'll be able to backdate to "yesterday", with very low chances of hitting cert expiry issues (but I wouldn't be surprised if OP's issue involves components outside of their control or ability to test end-to-end)

I should have written something along the lines of "validity date ranges" instead of expiration: you're much more likely to run into problems where you run into a certificate that was issued in the future relative to when you think is now.