The register is confusing.
When you issue a Check Pay quicken places the date you summited the request for the check to be printed calculated by quicken the time it needs to arrived to the vendor. and that is fine. However when you look at the register and the check has been clear by the Bank, that indicates the check has been cash by the vendor and the register should reflect that date you didn't NOT have that expenses till the check is clear. On old traditional paper accounting ledgers that date is annotated in order to keep track of accounts payable etc.
But with quicken we are dealing with a present accounting system that can register the actual pay date so Quicken should and must update of the Check Pay Date to the actual clearing of the check.
One good idea is to quicken move the Date to the memo area and place the actual date on the Date register. (Notice that the memo area might have some information on it so the date should be appended to it) that will cover all quationable check issues when dispute with vendor with out the need to visit the banking institutions to obtain the clear date, plus at this point then is not a accounts payable.
I hope quicken sees the light on this!