So after travelling around northern Italy using the new Trenitalia system that requires validation for Regionale tickets purchased through the app here's what I found.
I confidently validated my fast train and connection tickets on a trip before stating out, but the train was delayed and I missed the connection and had to buy replacement tickets for the second leg. The app does allow for refunds inside the app.
Okay, that was handy but the lesson learned was don't validate the tickets until you're sure the train is leaving and you're going to be on it.
The process seems to be having some introduction issues. One morning getting on the train in Siena I repeatedly got a series of different errors when I tried to validate my tickets. Eventually the app showed the tickets as validated but the process was buggy and frustrating. This seemed to correspond to a change that you needed to validate your ticket before your scheduled departure time. No more validating your tickets after the train was underway and repeated voice recording in Italian and English warned about this - a lot.
I think the biggest downside is that you can no longer jump on a train that is about to leave the station and then buy a ticket on the app. This was the best feature of the app when I first started using it because it allows you to run directly to the platform if you needed to. Now if the train is sitting there you need to be sure you can buy the ticket and validate it before the scheduled departure time so if a train is there because it is running late you can't take it even if you're actually sitting on the train.
Now I would never advocate this, but it does occur to me if you were to get on a train when it is too late to purchase a ticket and you knew there was a stop in just a few minutes you could book a ticket from that stop to your final destination and validate that one instead. Assuming no one is going to check your ticket between Padova and Vicenza - just as an example - you could get on a train leaving Padova five minutes late (for which you can't buy a ticket) and then purchase one from Vicenza to Verona rather than wait an hour for the next train. Just as an example.
But any system that you need to start working around tells me it's not working correctly for your customers. I saw a lot people still using paper tickets and I'm sure what further changes they may make. I think allowing people to validate tickets with in 5 minutes of the trains actual departure time instead of the scheduled time would help this a lot.
Just one more wrinkle to Italian travel,
=Tod