This is the FIFTH flat tire I have had on my trailer in the last two years and I only use the trailer 5 or 6 times a year to go to the vet. Three of those tires were brand new. I use the trailer once and when I hook up again the tire has a nail in it and is flat. Always the back tire on the passenger side and always on the sidewall or close to the side where it can’t even be patched to use as a spare. No flat tires on my car or truck, just the trailer. And road hazard is not an option for trailer tires at NTB.
This is getting old!!! Edited to add that this nail looks exactly like the nail that was in in the last new tire. I can’t exactly remember the prior nails.
Not a roofing nail.
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check Discount Tires, I pretty sure they offer " Certificate for Repair, Refund or Replacement"
If a tire covered by the Certificate for Repair, Refund or Replacement fails due to a non repairable road hazard or manufacturer defect, has 3/32" and above of tread depth remaining across the tire, and it has been less than 3 years from date of purchase, Discount Tire will give a refund of the full purchase price, together with the applicable sales tax
https://www.discounttire.com/customer-service/certificates
I would check and photograph the trailer tires after every trip and then recheck them before any trip.
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Please don’t kill the messenger, but what you describe indicates that it is your driving that causes this.
Horse trailer tires are about 8 feet apart on the axles, measured from the outside of the right tire to the outside of the left tire. Car and truck tires (duallies excepted) are around 6 feet apart. So the trailer tires are following a track which is 2 feet wider than the truck track.
You might just be hanging the passenger side trailer tire off the road shoulder or pretty close to it, which would explain why the outside of the passenger side tire on the trailer is the tire that is picking up roadside nails.
And why the back trailer tire? A WAG, but perhaps the front tire uncovers the nail, flips it up or uprights it, and puts it into perfect stabbing position to go into the following rear tire.
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Not a roofing nail, more likely fell out of a carpenter’s trailer hauling their trash.
We had some of those, on the side of the road, when the house was built.
Builder told them he was charging $5 for every nail he found on the road in and out, as it had to be theirs, triple if a tire found it. 
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If you ever ride your bike on a truck route (which, in my area, has larger shoulders than country roads) - you would be amazed at the debris on the shoulder. It’s actually pretty unsafe to ride a bike at all because of the incredible amount of road debris including nails, screws, nuts/bolts, springs, cotter pins, etc that are falling off trucks/trailers…not to mention just random crap, broken glass, empty bottles, etc.
It’s kind of hard to notice when you’re driving - if you look at the road near my house it looks like a perfect place for cycling. Until you actually do it - and then the debris is really visible and seemingly never ending.
It may not easy to stay out of the shoulder lane, and seem safer if it’s wide, but maybe move into the lane as much as safely possible to avoid the debris.
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That could be very well true. The county road where I live is about one and a half lanes wide and is full of pot holes. So I do have to get on the side when car comes the other direction and sometimes when the pot holes are in the middle of the road. But I never drive more than 15 to 20 miles an hour on this 2.5 mile stretch and about 5mph when I get off on the side. I don’t think I am hanging off on the side on the normal roads because I am a very cautious driver when towing but who knows. And I have also entertained the idea that the front tire flips the nail up and it stabs the back tire. So that means to me that I was going faster than 15 to 20 mph when I hit the nail. But I could be wrong.
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I need to buy that. These tires are always about 3 months old with 200 miles or less on them when I find them flat. This last tire was 1 month old with less than 100 miles.
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The strange thing is that I have an 8 foot by 16 foot flat bed trailer that I make trips out of state to buy hay. Never had a flat tire on that one. And I didn’t start getting flats on the horse trailer until I replaced the original tires with new ones. It just can’t happen unless the tire is new it seems. But I will damn well make sure I am not giving way my side of the road again.
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That actually looks like a roofing nail to my eyeballs. The hammer in by hand kind, not the nail gun type. If this were me, I’d grab my wheelie roofer’s magnet from the barn* (or buy one, they are not that expensive) and go over every square inch of my trailer parking area three or four times in several directions to see if I picked anything up. If nothing gets picked up at least you know your parking space at home cannot be blamed … or your tire already picked them all up 
If nothing, I’d also check the other place I park (if it’s been the same destination each time you’ve ended up with a flat) to rule that out. When those are both ruled out throw hands and swear a lot.
The parking space at home makes most sense to me (provided you back in or wheel around that only your back passenger side tire would drive the same spot every time) because you make it home ok and it’s kaput when you want to use it again. I mean sure, you could be picking up a random nail in a back tire while driving, I suppose, but flats I’ve seen on trailers due to unavoidable/unseen obstacles on the road tend to be front tire.
p.s. I had this problem with my car at work a few years ago with old nails that were surfacing through gravel from a many years ago sloppy tradesperson. Once figured out and cleaned up, I had no further problems.
*where it lives to make cleaning up snipped, pulled, and dropped horse shoe nails super easy 
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Yes I do back down my drive to the overhang on the barn where I back my trailer in. The drive is gravel and so is the overhang and I wouldn’t put it past some of the people that have done work out here to drop nails. But nobody has done that kind of work for years. Not horseshoe nails. My horses are all barefoot and the one that used to have shoes - she was shod at the vet. But it sure looks like the scenario an OP suggested - I hit the nail with a front tire which sends it airborne and it stabs the back tire. Especially this nail. It was on the INSIDE rim of the tire and only halfway into the tire. But of course pierced it enough to make it flat. I am not sure backing up 2 mph would have done that.
I didn’t say it was a horseshoe nail? I said it looked like a roofing nail and that I keep my roofer’s magnet at the barn. It may as well be put to use as wait for me to re-roof my garage again.
Also, the nails my car was picking up at work - old and rusty from years ago, not recently dropped, not horseshoe nails, not roofing nails.
Either way, I hope you’ve picked up your last nail. Flats suck. Flats on horse trailers suck worse.
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Has it been raining? I just got my second flat in about a month (maybe two) on the same tire on my Prius - passenger rear. Super frustrating. Tire guy said that when it rains, gravel and dirt roads have all the junk in them wash up to the surface.
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No
What kind of trailer has a skinny tire like that??? I thought it was a bicycle tire… Must be the camera angle.
Just a regular old nail. My husband commutes pretty far to work and has picked up a variety of different nails while driving.
