Practical Travel Safety Issues - Corporate Travel Site Not Asking for Known Traveler Number

My company’s travel site (which I’m required to use) asks all the usual TSA questions, except "Known Traveler Number". Should I be worried that my PASS ID is not getting sent to TSA and thereby reducing my likelihood of getting selected for PreCheck?

You should contact them (the provider) and ask, they may be able to manually enter it on their side. It's just possible they have not gotten around to fixing the screens yet.

Outdated software. This is an IT-fixable issue.

Our site is exactly the same way. They're in no hurry to fix is, even though our primary contract carrier is AA (and DL is secondary).