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Every couple of days, and I then cross check the transactions with the receipts in my wallet. If the receipts is needed then I store it away, other wise I shred them.
By Thursday most receipts have gone and been dealt with.
I always thought I was pretty good at this. Not quite down to the penny, but pretty aware of everything that should be going through.
Then last year, I signed up for a month's free trial of Netflix. Never used it, but completely forgot to cancel it and I only noticed the £7 dd going through 4 months later. I called them and they refunded the whole lot, thankfully (I presume they could see that I'd never used it).
I guess because it was only a small amount and it was coming out the same time as 9-10 other dds, it got through.
I'm pretty bad at this sort of thing. A few years ago I changed home insurance and they told me they'd take care of cancelling the old policy from the previous provider. It took me 6 months to notice that I was paying twice each month - they hadn't done anything.
I'd notice the big stuff, but my attitude tends to be that life's too short to worry about every penny. Which is probably why I'm poor.
I check my personal accounts every day, as I can just look them up on a phone app in a couple of seconds. I have regularly monthly payments set up as reminders in the calendar app, as I tend to keep most cash in the savings account and move it over to the current account as and when its needed.
My business account I probably check about once a week, just to remind myself how much is in there; there are only three monthly payments out of that, not counting paying the employee's salary and awarding dividends to the shareholder
I get a weekly text for the business account which is enough to see if the last invoice has been paid I check the current account probably about once a week or so, much easier now I've installed the phone app for it. I know what's going out, when, and how much, so the balance is never a huge surprise to me. It's not a joint account though, so that helps!
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