I try to handle it delicately but firmly (emphasis on try). I've created the order of priority and filing system to ensure that everything is as clear and simple as possible. The stumbling block is when the emotions kick in about financial insecurity. I call it separation anxiety from money. It's a basic fear that we'll run out, but when a bill or payment gets shorted (for absolutely no reason) the penalty exacerbates the next billing cycle. There goes more, for no reason other than being afraid that we'll run out before the next paycheck- which we never have.
Last month a guy showed up with a repo order and a tow truck. After a couple of phone calls to figure out why- I find out that there is way more than enough to cover the arrears, monthly budget, and a decent amount left over.
Then, when I sit down and start doing them myself she gets upset and takes it as me judging her to be a failure- Then comes more emotional stuff and rational thoughts and actions go out the window.
I've actually asked that she see a counselor or therapist for the deeper issues that drive the behavior, because there is no rational reason that any of this should happen, and anything I say is interpreted as criticism.