I've been in the room more than once where this conversation has happened:

IT guy: We must upgrade our shockingly ancient [database|OS|whatever]. The long term support patching costs are $X thousand and we are out of compliance with corporate security policy and they are threatening to deny our exception.

Exec: How much does the new license cost?

IT guy: $Xk + $1.

Exec: Is corporate security going to pay for it?

IT guy: They don't usually do tha...

Exec: No.

IT guy: Bu...but...

Exec: One more word out of you. Just one more word. Fucking try me.