Yes you can. The seating carriages run as a regular IC service. The seat reservation costs 3€ through OBB and 4.90€ through DB.

You won’t get a great night sleep but if you can crash afterwards at home in your bed it should be fine :)

Btw if you don’t mind the detour, take the stunning Bernina Railway between Milan and Zurich. Even better value for your pass day hehe!

Trains run hourly via Tirano, Pontresina, Samedan and Chur.

Sure you can, you can finish a journey on the last train boarded on a travel day, even if it reaches the destination the day afterwards. You can’t take another train the 07/05/2024 with your pass.

Since you take the IC carriage, the 4,90 EUR (DB) reservation seems allright (or 3 EUR at ÖBB).

Yes, as long as you don’t take another train the day after and the following day lies within the validity period of your pass, you will be fine. I even had a similar situation using the same night train in the opposite direction last summer.

And yes: The 4.90 € reservation is enough for that train (it’s even not required to reserve a seat for the IC part but strongly recomended of course) because it’s branded as a DB IC. However, I  wouldn’t stay in a seat car cause on this route, they often use open space carriages.

You can also get your reservation for 3 € using the ÖBB website.

Thanks for your answers. There are very helpful :)