Where are you located? What are your current temps? Also what method are you using to hand-pollinate?

Apparently, Pineapple IS an Open Pollinated, bi-colour, beefsteak tomato. It is late to set fruit, so hang in there! Could be that it's very hot, and that is causing the blossom-drop. I'd keep pollinating it, just in case it will help. (I gently buzz the blossoms with an electric toothbrush). There's not much else that you can do.

Linda

And, oh yeah, how many flowers has the plant had? Are we talking a 6 foot plant with tons of flower clusters that are all dropping? Or is it just the first couple of flower clusters?

In addition, how are you fertilizing the plant?

i wouldn't worry too much. it will start when it's ready.
some of my tomatoes were dropping flowers while others (sitting only feet from the dropping plant) were setting fruit.

some tomatoes (the actual fruit) also grow very slow, while others grow fast.
i have a Black krim that is 7 feet talll and has flowers and fruit everywhere.. problem is, it keeps putting out flowers/fruit while the other tomatoes that formed previously are growing in size very slowly.. yet, a plant right next to it is doubling in fruit size every week.

the Mortage Lifer i have growing is also the complete opposite.. 7 feet tall and only about 3-5 tomatoes on it and only a few flowers.. no flower drop, just not many of them..

so as you can see, some plants just don't all grow uniformly, despite planting at the same time and in the same growing environment.

@ gorbelly I am your neighbor SE to SC PA. Mid 80's to 90's for temps. For pollination assistance I give the plant a shake or use my finger same as I do for peppers at times. All the flower clusters from the bottom to the top, it's probably had 6-8 separate clusters form and die. They are probably 4 1/2- 5 feet tall. Fertilizer- very early spring black kow compost applied before planting, Alaskan fish, Alaskan seaweed, and osmocote slow release granular ferts sprinkled in the raised beds. The one in native soil I used some black kow compost only.

@Labradors thanks for the info, if the are late to the game, I sure hope they start setting fruit soon.

@Stevie thanks for all the info you provided, when set after set of flowers are dying off and the rest have some fruit set I was wondering if I had a dud plant, not even a single one set. I will try to be patient and see what happens over the next week or two before I consider them garden space wasters and yank them out.

My tomatoes always set fine in mid-80s to 90s temps.

Are the sepals staying on the plant, or is the entire flowing falling off at the "knuckle"?

And I would cut back on the N in the raised beds and make sure to give them a bit more P and K. Flowers that don't set even though plants are big and healthy can be a sign of excess N. The plant in the ground may just have a general lack of nutrients--Black Kow is more of an amendment than a fertilizer. I would give a bit more nutrition to the in-ground plant, making sure N is proportionally less than P and K

But likely a contributing factor is that the variety is a late-setting one, as Linda said.

You can try to help things along with the pollination assistance, but I'm not sure what "use my finger" means. Tomato flowers do not have exposed pollen, and many do not have exposed stigmas. So if you try to move pollen by touching the ends of your plants with your fingers, that won't do anything. You need to shake the pollen loose from the tubular structures that enclose them so that the pollen drops down the anther cone and makes contact with the stigma. So give the flowers a few good, sharp flicks or use something on them that will buzz/vibrate them like an electric toothbrush, a tuning fork, etc. Think "dislodging" the pollen, not picking it up and moving it around. Shaking the plant is not as effective as flicking the blossoms, and that's not as effective as buzzing them.

I had a tomato plant that didn't ever set fruit from its many blossoms last year. Not pineapple but another variety that I had grown before. Plants to the left and right bore good crops. All were treated the same and had same amount of sunlight. Also used the vibrating toothbrush trick on all my plants.

Not sure what the explanation is but I have read that occasionally that happens. First time in 50+ years for me.

Hope yours is just a result of a late variety.

Weird. My Pineapple tomato plant isn't setting fruit either. My 16 other varieties are doing great though and I should start seeing ripe fruit in a couple of weeks. All of my plants are treated equally and they are all mid to late season varieties, so not sure what is going on. I have had success with Pineapple in the past though so I guess it's just a fluke.

I also have a variety of tomato plants all are doing amazing standing at 5-6 feet with many tomatoes (green) right now but my pineapple tomato only has one flower but is thick and stands about 4 ft tall! Hoping to see tomatoes on it at some point!