Flying MXP-EWR arriving into EWR at 1:45pm and wanting to overnight in NYC before flying home to SFO the next day. Economy, one way award. After multiple calls the best I can do in terms of routing is a 7am departure out of Newark the following day. There is award availability for the 1:30pm departure. That departure would be within the 24 hour allowable connection that I thought was a rule when connecting via a gateway city on a multi region award. The agents keep telling me the system will not allow that to be booked without collecting an extra 12,500 miles. I tell them about the 24 hour rule and the supervisor says the system won't allow it to be booked as it is "close to 24 hours" (other departures such as the 9am departure are also not being allowed but the 7am departure is). I've asked for the agent to look up the rule and am on an extended hold waiting for a response.

Is it possible United now has an unwritten 18 hour layover policy? (the 7am departure falls within 18 hours or so other rule that is preventing this). I've been able to ticket up to 24 hour connections as a single award as recently as earlier this year. I've tried calling twice with extended holds and supervisor intervention and had no luck. After the agent reached out to a third supervisor that supervisor agreed that allowing me to book the 7am but not the 1:30pm made no sense and she did a manual exchange and got me on the later flight.

The 24 hour connection is important to me as my wife and I often fly economy and she has a bad back so it's more comfortable for her to break up the journey with an overnight.