Originally Posted by OSULugan

OP here, just catching up after being back from vacay and the holidays.

To clear up a few facts:
1) Both reservations (HGI and ES) were made using a credit card, and neither were points stays / pre-paid.
2) I had missed my cancellation window on the ES, and got extremely lucky that I hadn't, otherwise we would have been beholden to availability of alternate accommodations (which would have been the RI).
3) I mentioned the RI because there was alternative properities in the nearby area (this is just a few blocks away from the HGI) where there were rooms accommodating our party size available. But, HGI refused to "walk" us. Our options were to violate fire code (cramming into a room w/ max occupancy of 4), accept the non-connecting rooms, or find our own way, and have them cancel the reservation at no cost to us "as a courtesy".
4) Hilton Customer Service, after having me on the phone for ~ 45 minutes that evening, regardless of the resolution credited me 20k points. I then received 30k points as a resolution, and then another 40k points when I pointed out that wasn't enough. The grand total was 90k points. Which, while it is a lot of points, if I can't use them for reservations because I can't trust the confirmed connecting-rooms, and I don't use them for work travel, they don't do much for me. My original request was for cash reimbursement of the 1st night at the other hotel (basically, force the HGI to pay the "walk" price that they should have done in this situation). When I got a 30k point reimbursement, I used the 70k point / night cost to indicate that the 30k point reimbursement falls far short of what a single-night cost was.
5) The "boss" is my wife.

In the end, we enjoyed our trip, we liked the ES there in Midtown, I got lucky by not having to pay a cancel fee on the ES or the HGI due to my mistake.
But, as a result of this experience, I was 50/50 on getting the conecting rooms that I had "confirmed" according to the new Hilton feature. And, that is what the post is about. I'm only a single datapoint, and there may be other people that have no issues with this feature. But, this data point suggests that if the connecting rooms aren't available, as promised, you might have some headaches and a late night ahead trying to figure out where you're going to stay.