Know what you spend. Receipt scanner

18cc

I would definitely recommend looking at opening a bank account with monzo and using their debit card for your spending as they have pretty much what you want

you can categorise your spending look at monthly summaries and so on

gingercordial

At my place of work we use Concur for expense claims. That is supposed to take a photo of your receipt, analyse it and extract the relevant data (amount, date and so on) and attempt a categorisation. You can then manually fix any errors.

Almost every time it gets something wrong. Or sometimes everything. Receipts are often not clearly printed, or are folded/crumpled so won't lie flat to photograph, or the light isn't quite good enough, or the background you have is something that the app can't distinguish from the receipt itself, or the receipt is too long or double sided. Even in perfect conditions half the time it misreads 0/8 etc. The automatic categorisation is a joke. It's actually more annoying that just manual entry from scratch, so most of the time I don't bother. (Given I am a staunch MSE'er it is quite telling that I let my expense claims build up - risking losing receipts and providing my employer with an interest-free loan - because I can't be bothered to deal with the Concur app that often.)

If you can build something more accurate than Concur that would be awesome but I expect they have already thrown a lot of money at the problem and still can't get it to work well.

For my personal spending I use YNAB to track everything. My husband and I have a shared budget on there which we can both enter to, and it syncs between us via Dropbox. It is manual entry but I think that's helpful in really understanding what you're spending, rather than being passive about it. Having to enter your spends from down the pub (or whatever your vice happens to be) focuses the mind on the amount ;-) So we have both trained ourselves to enter all transactions, regardless of the source of funds, straight away. It isn't so bad doing the manual entry once you get used to it.