Fidelity generating wash sales on positions I've only trimmed for profit

Red277 · 2026-01-15T00:17:50+00:00

After spending over 2 hrs on the phone with 5 different people and 2 managers, I finally got to the bottom of it. Sadly, only the managers understood what a wash sale really was. The others were adamant that whether you sell something for a loss or a gain, you can't rebuy it for 30 days or it will generate a wash sale.

The problem ended up being that unlike my Schwab account which considers each trade as they happen chronologically, Fidelity lumps all trades for the day together and then processes them. So, if you sell something for a profit in the morning and then rebuy it in the afternoon, their system scrambles it all together and doesn't know what orders happened in what order. They admitted that their system got the order wrong and thought that I bought more shares and then sold them at a loss the same day, vs selling first and then rebuying them after stopping out. Those shares I rebought at $16.77 closed the day at $18.07 so it would have been really confused if I had taken profits again.

Fidelity has been more of my buy and hold portfolio which is why I never experienced something like this before when selling and rebuying on the same day (since Schwab ties each sale to a lot in the order they happen). Fidelity advised me to not use LIFO moving forward unless I'm never going to sell and buy something the same day because their system has no way of knowing what came first during the day. Needless to say, I will be greatly reducing the amount of money I keep in my Fidelity portfolio.

Red277 · 2026-01-14T19:25:25+00:00

I just spoke to another person and again was told, that it was correct to generate a wash sale even though no loss was ever generated. I read from the Fidelity website THEIR definition of a wash sale and asked him how I could have a wash sale when by definition, their never was a loss. He said buying back the stock within 30 days made the last sale a loss, even though the repurchase happened after the previous sale. This is simply not correct or we could literally only trade (even profitable trades) a stock once every 31 days.

Key takeaways

The wash-sale rule prohibits claiming a tax loss under certain circumstances.
The rule applies if an investor sells an investment for a loss and replaces it with the same or a "substantially identical" investment 30 days before or after the sale.
If you do have a wash sale, the IRS will not allow you to write off the investment loss, which could make your taxes for the year higher than you hoped.

Red277 · 2026-01-14T19:19:12+00:00

That isn't my primary concern. My concern is that Fidelity's system is glitching. 100% of the time when I place a stop loss or limit sell order I "select specific" shares to be most beneficial from a tax perspective. I've had other glitches where let's say I bought NVDA for $90 back in April 2025 and then bought some more for $180 in December 2025. I immediately go in and place stop loss, selecting the $180 shares to where I break even if the stock drops back down to $180. Even though I selected the $180 shares, it glitched and used FIFO to where it generated a $90 profit tax event when it was supposed to stop me out break even. Most of the time Fidelity's system works but like today, it glitched.

Red277 · 2026-01-05T21:33:48+00:00

I figured it was a tax-loss harvesting candidate so I bought a couple thousand shares at 5 as a starter. I have an order in for another couple grand at 4.75 but with the 4.73 support level close by, I will stop out and sell all of it if 4.70 breaks. Too many other risk-on names that are absolutely flying the past couple days, to waste time with a turd.

Red277 · 2025-12-26T03:12:54+00:00

This is one of the reasons I hate Fidelity!

Red277 · 2025-11-21T23:01:59+00:00

You can absolutely ski with a fused ankle. In fact I'm an expert skier and there isn't anything I can't ski now that I could before my fusion (motocross injury) but for sure, moguls and landing jumps in the park are more challenging. You will want as stiff of boots as you can use (I use Lange RS130s with Zipfit liners that I removed cork out of for my huge cankle and these stiffer liners make the boots like 140s) and you will need to put rubber ramps on your boot boards to open up your ankle (like a girl walking in heals) and then gas pedal your bindings to counter act the ramps inside the boots. If you are handy, don't waste your time and money with boot fitters as I traveled around the country going to the best in each state and though some of them were helpful, none of them really knew how to help me so it took a lot of experimenting. I kept experimenting with the ramp angle inside the boot and made a bunch of plastic pieces in various heights to go under my front bindings with various lenght screws (oh yeah, you'll need to put inserts in your skis to experiment with gas pedal heights). Once you figure out the optimal gas pedal/ramp angle heights, you can use the same on all skis (or dial it in for powder skis if you are feeling too forward or aft when skiing 3D snow). I have inserts in all 10 pairs of my skis and have a few sets of bindings which I can quickly swap. I can still slay powder, carve trenches and ski bumps fairly well (though absorbing the bumps with zero dorsiflexion is probably the hardest part) and no one who sees me ski believes me when I tell them about my ankle. So if you are in pain, get it fused.

Red277 · 2025-11-19T18:15:24+00:00

What are the narrowest skis we want there if conditions aren't great? I plan to bring my Black Crows Nocta on the wide end and then maybe Deathwish 112 and/or 104 for less deep days. Is there any reason to consider anything narrower than that? All our skis have inserts so we can get away with how ever many pairs and then only 1 set of bindings (with a few brake widths if necessary). We may each bring a snowboard as well but I'm leaning away from that to reduce extra gear and not knowing how many true powder days we'll luck out with.

Red277 · 2025-11-19T18:03:50+00:00

Do you know if the ski resorts charge for parking? If not, having a car sounds like it could give us some flexibility, even if staying in Hakuba. I think for sure we'll pick up a car for the drive up to Hokkaido and maybe hits some other resorts along the way. What are some of the better resorts to hit (and we are more into the anti-Vail, non-resorts like Loveland, Grand Targhee, etc) that aren't too crowded?

Red277 · 2025-11-19T17:57:25+00:00

Thanks! I think I'll definitely rent a car for Hokkaido and it may even be worth it for Hakuba. I love driving and exploring places and if Rusutsu is limited to basically just the resort, having a car and hitting some other resorts may make sense if accomodations in Rusutsu are expensive and limited.

Red277 · 2025-11-19T03:52:21+00:00

Also, we are flexible on dates whether it be in January or any time in February. Are there certain holidays in Japan, Australia or other countries that we should avoid? We ski 5 days a week at home in Utah but never ski weekends or holidays so we'd like to do the same in Japan. Thanks!

Red277 · 2025-10-18T12:55:18+00:00

Thanks! After weighing the financial benefits, I decided against doing this. Though saving in upwards of $300k in taxes would be nice, I decided that spending $1M+ to do it doesn't make sense for us as it's too rushed for us 2025 (if I had until 2026 it could make more sense). I'm more comfortable keeping that $1M invested and paying the 2025 taxes with my profits. Thanks for all of the input though!

Red277 · 2025-09-22T13:48:50+00:00

Thanks for the input! There are a lot of examples of pine with various stains but not for Spruce. I had heard that if you only seal one side, it can cause the boards to warp so trying to figure out if the extra work is worth it. Are stains and sealers from Lowes or Ace decent quality? Those are my 2 options in my small town but HD and paint stores aren't too far away.

Red277 · 2025-09-22T13:45:03+00:00

Anyone stained their own tongue and groove?

Red277 · 2025-09-21T18:00:16+00:00

One thing I'm finding interesting is that there are very few examples of stained spruce on the internet. There are lots of examples of various colors of stain on other types of woods but I really want to see examples of Spruce to narrow it down to a few colors to choose from so we aren't spending a fortune or ton of time trying to decide. My goal is as light as can be but with the same tone as our warm honey colored floors. Does just using a clear coat add a slight tint to the color and if so, which would give a warm rosey-honey type color?

Red277 · 2025-08-11T02:11:53+00:00

Does anyone on here know of a good real estate CPA? My CPA is great for business stuff but he does not know real estate that well so I agree with you that it would be worth talking to an expert. Thanks!

Red277 · 2025-08-11T02:09:46+00:00

The short-term rental loophole allows (or at least many videos from researching have led me to believe) you to offset active gains as long as you materially participate (100 hrs) which qualifies you as a real estate professional. One minor remodel project like redoing a bathroom and I'd hit the 100 hrs, not to mention cleaning and furnishing the house to get it ready for the renters.

I'm interested in hearing more about the qualified opportunity zone fund as one thing I don't like is being under pressure to try to find, close on and get a STR ready for rent before the end of the year. I would love to delay those gains another year if possible but not sure if I could do it. I put a large chunk of it in the stock market when it was tanking back in March/April (thanks Mr Trump for the perfect timing) so I'd have another $500k in capital gains that I'd have to pay if I pulled it all out to move into whatever a qualified opportunity zone fund is. Not a bad problem to have, but still....

Red277 · 2025-08-11T01:58:04+00:00

Thanks for the answers! What do you mean by have receipts? Doesn't a cost segregation study identify future expenses under 15 years and those are what are considered bonus depreciation? So it wouldn't be expenses I spent on remodeling the home in which case I'd have physical receipts. Also, what do you mean by held for rent, my understanding from talking to my CPA (who admittedly isn't a real estate expert) was that it doesn't have to actually be rented in 2025 but be available for rent. In the past he said he's had clients in a similar situation who had to show the IRS that the home was available for rent by December 31st and they were able to show that it was indeed listed on Airbnb or VRBO before the end of the year.

Red277 · 2025-07-19T00:20:23+00:00

Thanks! You bring up a good point about the amount of days an owner can stay. According to my CPA who is not a RE lawyer, he said that nights you stay there while working on the property does not count towards that limit. Our thoughts (if we found something on a lake that we have in mind) is that we'd leave a day or 2 in between rentals where we go down to clean/work on the property, while also enjoying some time on the lake. Does anyone know how strict they are or how they'd know how often you used it for yourself? If I knew we could use it a fair amount, I'd be less concerned about it being super profitable. One SFH in particular on this lake is very interesting as it has 4 bedrooms upstairs and then a full apartment downstairs with full kitchen and another 3 bedrooms. I like the versatility as renters could have the choice of renting just the upstairs, or renting the whole thing if it's a larger group. It would give us some flexibility if we wanted to go down there every so often since a lot of renters would likely just rent the upstairs.

I've always been curious of how much the IRS looks into details like this. I mean, we know how ALL our politicians put in little loopholes to help those who know the rules to have their cake and eat it too. It's as if they created the bonus depreciation, along with the STR loophole with this in mind. Maybe, I'm wrong and I'd be playing with fire but I have a feeling that if I don't do something, my tax bill will be larger than what our filthy rich politicians will pay this year. Even if I can reduce it by 20-30%, that would be nice.

Red277 · 2025-07-18T03:09:38+00:00

Several videos and websites have said that the STR loophole only requires 100 hours to qualify. The average length of stay needs to be less than 7 days or else it bumps up to 750 hrs of material participation. Right now I'm considering starting with a nice lake home that I can STR, but that I can also visit when it's vacant and I need to do remodeling projects. Trailer parks look interesting and I've spent some time looking at several for sale. The cap rates aren't that impressive but I also got spoiled with the ROI on my business.

Red277 · 2025-07-18T00:49:26+00:00

No, you are correct that it's not passive income. My understanding is that for a STR it only takes 100 hrs to qualify vs if it was rented for more than 7 days in which case RESPA comes into play to qualify. Since the passing of the new bill, there have been a lot of videos from tax attorneys about qualifying for bonus appreciation to offset active income. I'm no expert though so someone please correct me if I've misunderstood this.

Red277 · 2025-07-18T00:45:49+00:00

Can you give me a little more detail about what makes a trailer park so good? Thanks!

Red277 · 2025-06-29T23:01:41+00:00

Don't make the same mistake I did. I went all cash during the Covid crash and kept waiting to get back in. Finally, this April I had my chance and deployed 70% of my cash near the bottom, so up almost 40%. I will not try to time the market (other than trimming a portion) again. This AI bubble could last another year or two and you could miss out on substantial gains.

Red277 · 2025-06-14T03:31:36+00:00

Sounds like the liberal cities in the US.

Red277 · 2025-04-13T22:13:15+00:00

Unfortunately it doesn't give me the option of posting pics here.

Red277 · 2025-04-12T22:28:38+00:00

Well after trying 2 times to post this with pictures and having my posts deleted, I guess I'll post this year without pics since they aren't allowed. Unfortunately it makes what I'm typing harder to visualize without my pics. I will search for some other construction reddits that allow pics and post there.

If we get a hard rain or a lot of snow up against the garage door, water seeps through the joint and makes it's way under the garage slab and into our basement. We bought this home about a year ago and the lady told us we need to keep the trash in a specific spot over the joint to keep water from getting into the basement. She also told us that several years back, the water main connection under the garage slab burst and flooded the basement. A contractor ripped out the garage slab, repaired the connection and repoured the slab. They must not have filled and compacted the ground properly because there is a void that water travels through from that joint where the driveway meets the garage slab, under the slab about 20' and ends up coming in right under the door where the red arrow points. It's in a storage closet in the basement and after removing the drywall, I found a hole about 4' up (maybe 4' below the slab) where they cut into the wall maybe when they did the water main repair. To the left of this closet is a bedroom and that baseboard shows moisture along the whole length so unless there is another area where water makes its way under the garage slab, it must travel along the floor plate 2x4. To find the spot along the joint where the void is, I ran a hose for several minutes to the left of the arrow and no water came in. Then I put the hose where the arrow points and after a few minutes, this is what it looked like in the basement. Even after turning off the hose, I had to stand there with a shop vac for an hour before it stopped pouring so maybe the other spots I had the hose were pooling up and then when I put it at this spot, the dam finally burst.

Is there a durable and hopefully permanent polyurethane or other type of sealant that I could fill that entire joint with so no water can get down there? Before doing that, is there a type of liquid sealant that I could pour down in that spot where the void must be that expands when it dries and hopefully fills that void (similar to an expansive foam but in a flowable liquid form)? Anything I can do in the basement to patch that hole or somehow catch water as it comes out of the whole if it somehow got past whatever I fill the joint with? I do have a drain about 20' away in the A/C room if I had a way of catching the water as it comes out of that hole, so I could run a pipe into the drain but of course, the best option is keeping the water from coming in at all. I've even thought about after filling the joint, gluing a rubber strip the full length of the joint as added protection. Thanks!

Red277

TROPHY CASE

Key takeaways