Odd error booking "stopover" flights
 

Anyone know why this error occurs?

I wanted to book an itinerary of AAA-BBB / BBB-CCC / CCC-AAA, where BBB-CCC and CCC-AAA are separate legs on the same day, with a several-hour stopover to allow for conduct of business.

Trying on AA.com gave the following error message for a paid flight:

Something went wrong
You can't book connecting flights as individual flight segments. Please change your flight search. Contact technical support.

When trying it using miles, however, the same itinerary was acceptable (and priced as 3 flights/trips).

Interestingly, trying to book the entire itinerary on Kayak gave no problems. It was possible to click through the link from Kayak to aa.com and book with no error message.

Likewise, booking only BBB-CCC / CCC-AAA (on the same day) caused no problems on aa.com for either paid or miles tickets. [Disclosure: I ended up booking this part with cash and AAA-BBB with miles, both on aa.com]

Any idea why the glitch for the full itinerary on aa.com?

Thanks!

I've had this happen - if they don't qualify as true stopovers (where you stay longer than the allowed time 4hrs/24hrs), you can't seem to force the AA booking engine to spit them out. If you do a "multi-city" search, you get the message above. I've been successful in using Google Flights to do the search, create the itinerary, and launch the AA booking from there. That seems to work most of the time.

Just a note to add that domestic connection time is no longer 4hrs:

they gotta sell those married-segment 17-hour-layover mile sAAver tickets somehow https://www.flyertalk.com/forum/images/icons/icon10.gif

The "stopover" time was 5:45 or so.

What's bizarre is that starting at AA.com it could be booked as an award itinerary even though it would not generate as a paid itinerary. But starting at Kayak (and I would assume Google Flights) it could be booked as a paid itinerary – Kayak took me straight to the AA.com booking page with the itinerary all set up and priced.

Very strange.

In my case it was $11.20, but I don't know if that's because it was perceived as 3 flight legs or because it was perceived as having 2 legs with a "layover" of more than 4 hours during one of them. Probably the latter?