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Here is some information from Trenitalia about what can go wrong with online payments:

Thanks, Gala Placidia. Members may wish to note that a second transaction was blocked, not "piu di due" as on the above website. And the policy of not allowing more than two journeys booked online within 30 days (unless one gets special permission via a complicated 48 hour procedure) is certainly unlikely to encourage tourism by train.

I agree it isn't wonderfully easy to book multiple journeys - and they have (had) a rule which limited expenditure in one month to something less than €1000. Maybe that seems fine and generous, and it is if you are thinking about a couple - but even when you get towards family you might be struggling with this limit. But that's only the half of it. If you need to connect via a 'regionale', and you happen to board at one of the many statons which don't do a 'self service internet ticket' - you've paid, you've got the receipt and the even barcoded e-ticket - but the conductor doesn't have a bar code reader! So you are in the wrong! By great good fortune the first time this happened to me the strangers in the neighbouring seats were all in the same boat, and we were not going to put up with this - so (probably because he was clearly outnumbered) the conductor slunk away muttering 'this time...'. It is a shame, because buying a journey on a frecciarossa and having the four figure code on your cell phone as a ticket is mega impressive, but like so many things in Italy they can't carry la bella figura through to completion. I put it down to attention deficit disorder, learned, no doubt, from their premier il Silvio.