No one can definitely answer that question because it's up to the border agent you deal withs opinion. US passports do have a biometric chip with a digital copy of the photo inside which may make them more lenient than if it didn't have one. Depending on where you go though the immigration may not even have a scanner, so yeah, it's a risk.
If you've been allowed in at the border I doubt you'll have any issues with the extension. There's always the possibility though, nothing is guaranteed.
What if you enter twice by air then can you enter once by land? I feel like they might confuse the policy and say no, you've already had 2 exemptions, you can't enter by land.
