Is this a punt? Bluff attempt 3bet pot OOP on A high flop

UTG have very loose preflop stats, this kind of opponent is much more likely to call the squeeze than normal. In theory they are supposed to fold 80%+ of their range. When you squeeze 99 you really want to see 2 folds, because playing it OOP will be pretty tough on most board.
So for me preflop is already very borderline.

Flop is whatever, I guess you might get them to fold most of their pocket pairs?

Once called on the flop turn is just burning money.

Yeah as above said UTG looks fishy pre. They are also opening 3x from UTG, so you have a player who is probably opening the tighter end of their range and unlikely to fold. MP is then more incentivised to call too, making 99 very awkward to play.

On the flop you don't fold out much better as QQ+ will shove pre. Maybe TT/JJ if they didn't shove. You do clean up some equity by folding out broadway combos so I think cbet is ok.

Once they have called flop with MP still to act, I would assume they have an ace and are getting a good price to call your shove. At a stretch maybe A2/A4/A5s folds if they got here.

I think i bet flop smaller or even check. After that, just check and hope for a showdown i think.

Ok so thanks everyone for your thoughts on the hand. I will now go through what I was thinking at the time and how after looking it over I would play the hand differently.

So playing pocket pairs in this spot is really hard, and the natural reaction is for most players is to flat, but against a good reg which is how I perceive UTG to be, my hand is kind of face up. So I do like the theoretical range play here a lot more of just 3bet or fold a lot more. Obviously doing this with pocket pairs in general is really hard because a face card is coming up fairly frequently and OOP it's just more pressure.

So I would agree this is not a play you want to do often, just every once in a while pre-flop. And sure enough GTO wizard has 99 at around 40% raise range. Not sure how a cold caller affects this but I imagine not too much. Looking at the stats of V, I do not think he is folding a lot here and will call wider than he is supposed to which I think makes the raise even better not worse as boulgakov suggested.

So now it's an A high flop very static and dry. Obviously terrible for my hand, but my feeling is that if I am 3betting pocket pairs in this spot, I can't always be hoping for a set, I have to turn some of them into bluffs sometimes. And this seems like a good spot because in my mind all AK shove pre, and he is calling most of his other suited and unsuited aces. Only real hand I am worried about here is AQ and AJ here.

I think he flats TT and JJ pre at a very high frequency, maybe even 100%.

So with the Cbet only MP gets out of way, now I think V has an A and is sometimes getting stubborn with JJ,TT.

Since there are many more weak aces than strong ones I decide to go for the rough 3/4 shove which I think puts him in a real tough spot. From his perspective, what am I bluffing on such a dry board? 89d or 65d which to be truthful I am probably folding 100% of the time pre, maybe a suited diamond broadway which I check frequently trying to realize equity. So I would have to be turning something like JJ or QQ into a bluff. Not a standard play from the pool. So I feel he has a real tough spot with all his weak aces and I do think he shows up here with A7,A9,AT suited also in addition to all the wheel aces.

Anyway looking back now flop bet should definitely be a bit smaller so I give him tougher pot odds on turn shove. And perhaps the better play is check flop and jam all in on a small bet? I do think checking OOP incentivizes a lot of stabs in 3bet pots. Interesting enough GTOWizard is saying to check a lot of AKo in this spot pre from Vs position which I found interesting. If I thought he was doing this I would not make this play.

What do you think of this analysis any area you think I am way off?

Vecissitude bets 140.5 BB and is all-in,