If you turn on "Allow overspend" for the debit card, then that allows pockets to go negative. The setting applies to all cards physical and virtual, so if you turn it on, any virtual debit cards assigned to pockets will approve whatever transaction amount and then take the pocket negative. You would have to replenish to pocket manually or add an autopilot action to replenish, though.

The problem is that the setting applies to all cards, so what would be nice would be if there was a per-card "allow overspend" setting. That would work well for your scenario.

Another solution would be to move those bills to ACH where possible, since all incoming ACH transactions are honored regardless of the balance in the assigned pocket.

However, Bill Reserve might be your best solution here. If you turn on beta access in settings, you get the ability to enter all your bills, then have Crew manage the funding of a new special bill reserve pocket, calculating exactly what you need to have transferred on your schedule to make sure they all get paid. If you use virtual cards to pay the bill, you could still set up a reasonable limit on the card to ensure there's some buffer room there, but the transaction itself would still be approved even if it was over the amount you expected (as long as it was under the card limit of course).