4

It depends on the status of the stock. If it trades on the OTC market, sell the shares. If there is no market for the security, your broker may be willing to send you a letter stating that securities have become worthless. Some brokers are willing to buy them back from you for a nominal amount. To deduct the loss, the stock must be completely worthless. ...


4

The shares bought in your first 3 transactions were all sold on Apr 15th for a gain of $67 (+40 +18 +9). If you were to sell the 5 shares bought on May 5th for a loss in less than 31 days after the purchase made on May 10th, that would create a wash sale violation. Selling them now would not.. But that's not what you asked. You could sell the ...


4

You should be able to use the wash-sale rule against the IRS here: you sell the stock, and buy it back within 30 days. Then you sell it again in January, and that will make the loss applicable to Tax year 2020, and you have the risk only for some days. You can also repeat that every 29 days, and only keep it for five minutes each time, that has nearly no ...


3

In my opinon, https://fairmark.com/ is a reputable site for tax advice. Here's an abbreviated version of their take on the wash sale possibilities involving stock and options: If you sell a stock at a loss, it's a wash sale if you buy substantially identical stock within the 61-day wash sale period. You’ll also have a wash sale if you enter into a contract ...


3

Per the information on the form, you swapped one security for another as part of a "reorganization" and so do not have either a realized gain or a realized loss from the swap. Your basis in the 7 new shares is equal to your basis in the 60 original shares when you sell them. That means option 3 is the only kosher approach.


3

From IRS Publication 550, Investment Income and Expenses: When you figure the amount of any capital loss carryover to the next year, you must take the current year's allowable deduction into account, whether or not you claimed it and whether or not you filed a return for the current year. So based on your question, even though you had no tax liability ...


2

I'm not a tax specialist but have been in the industry for 20 years. It's a taxable event in the tax year of the sale. So if you sell it in 2019 you have to claim it on your 2019 taxes. The only portion that can be carried into 2020(or beyond) is losses in excess of 3k. Only idea I have is to look at an option strategy that expires in 2020. You might ...


1

There is no way to realize the loss this year and defer it until next year. There are some ways to use options to lock in the position until 2020, limiting losses but viability depends on the stock having options as well as the implied volatility of the options and the availability of strike prices.


1

The quick and dirty summary is basically that you have to be able to make a compelling argument to the IRS that you're trading as a business on short-term swings of the market. We can't give a definitive answer, and can't even really make an educated guess without a lot more information about how and how often you trade. Though the fact that you want to do ...


1

It looks like your ESPP has a lookback provision, where you get 10% off the lower of the FMV on the grant date (i.e. start of offering period) or the purchase date (i.e. end of the offering period). In this case the price rose over the offering period, so you get 10% off the grant date FMV. Since this is a disqualifying disposition, your entire discount ($16....


1

There is nothing about the wash sale rule the prevents you from trading anything. The wash sale rule simply addresses how you deal with the taxes associated with the loss. If it is a wash sale (ie you sell for a loss and repurchase a similar investment within the 30 days) then you simply can not claim that as a loss on your taxes. Under the rule if I have ...


1

The wash sale rule applies to losses from equities and options but not commodity contracts or foreign currencies. After a loss in the underlying, you can trade options as long as it's not a substantially identical position. So if you realize a loss on a long position in the underlying, you could buy a put but you could not buy a call because a call is ...


1

If the company went bankrupt, your year-end statement from the brokerage should show the stock as now worthless and report a loss equal to what you paid for the stock. This happened to me a couple of years ago. If it's an OTC stock and the company is still in business but you can't find a buyer ... hmm, I've never run into that situation. I'll yield to ...


1

I've never heard of Glacier before this, but I looked it up and found this: https://www.glaciertax.com/ It seems like this software may not know how to handle capital gains/losses. Under the section "What Does GTP Do?" it doesn't mention this, and the section "GTP Provides Everything You Need!" lists a bunch of tax forms it supports, but Schedule D is not ...


1

The fact is that if you incur a wash sale, the loss is disallowed and must be added to the cost basis of the second position and carried forward. More on this scenario with various examples can be found at The Motley Fool web site: https://www.fool.com/taxes/wash-sales-and-worthless-stock.aspx


Only top voted, non community-wiki answers of a minimum length are eligible