Is there a “reverse wash sale” rule?
Yes, the newly bought shares will have a long-term holding period, regardless of when you sell them.  In addition, it's only a wash sale if you sold the first shares for a loss; it's not a wash sale if you sold them for a gain. Wikipedia mentions this: When a wash sale occurs, the holding period for the replacement stock includes the period you held the stock you sold. Example: You've held shares of XYZ for 10 years. You sell it at a loss but then buy it back within the wash sale period. When you sell the replacement stock, your gain or loss will be long-term — no matter how soon you sell it. Charles Schwab also mentions this: Here's a quick example of a wash sale. On 9/30/XX, you buy 500 shares of ABC at $10 per share. One year later the stock price starts to drop, and you sell all your shares at $9 per share on 10/4/XY. Two days later, on 10/6, ABC bottoms out at $8 and you buy 500 shares again. This series of trades triggers a wash sale. The holding period of the original shares will be added to the holding period of the replacement shares, effectively leaving you with a long-term position.
I think it looks pretty good. Something about the reverse white typography seems a bit harsh to me what with everything else being in warm browns but that's a quibble.  I remember being told in some business course ages ago that one needed to be able to withstand 3 years of few sales when starting a new biz. That was pre-internet. There are probably new rules but I think one should still be prepared for a long wait. People have to find the site. How will they do that? In addition to the adjustment type in NL7's answer, there are a host of others.  If there are any adjustments, form 8949 is required, if not, the gains can be separated into short and long-term and added together to be entered on Schedule D.  Anything requiring an adjustment code in column F of the 8949 requires an entry in column G.   Some other example entries for column F include: (see the 8949 instructions for a complete list) **A wash sale occurs when you sell or trade stock or securities at a loss and within 30 days before or after the sale you: Buy substantially identical stock or securities, Acquire substantially identical stock or securities in a fully taxable trade, Acquire a contract or option to buy substantially identical stock or securities, or Acquire substantially identical stock for your individual retirement account (IRA) or Roth IRA. (from Pub17) The way the wash sale works is your loss is added to your cost basis of the buy.  So suppose your original cost basis is $10,000.  You then sell the stock for $9,000 which accounts for your $1,000 loss.  You then buy the stock again, say for $8,500,  and sell it for $9,000.  Since your loss of $1,000 is added to your cost basis, you actually still have a net loss of $500. You then buy the stock again for say $10,500,  then sell it for $9,500.  Your $500 loss is added to your cost basis,  and you have a net loss of $1,500. Since you never had a net gain, you will not owe any tax for these transactions. Wash sale applies. If you purchase shares within 30 days of that Feb 3 sell date, the wash sale kicks in, preventing the loss on that sale, and deferring it into the new shares. "Here's the detailed section of IRS Pub 590 It looks like you intended to have a ""trustee to trustee conversion"", but the receiving trustee dropped their ball.  The bad news is, a ""rollover contribution"" needed to be done in 60 days of the distribution.  There is good news, you can request an extension from the IRS, with one of the reasons if there was an error by one of the financial institutions involved. Other waivers.   If you do not qualify for an automatic waiver, you can apply to the IRS for a waiver of the 60-day rollover requirement. To apply for a waiver, you must submit a request for a letter ruling under the appropriate IRS revenue procedure. This revenue procedure is generally published in the first Internal Revenue Bulletin of the year. You must also pay a user fee with the application. The information is in Revenue Procedure 2016-8 in Internal Revenue Bulletin 2016-1 available at www.irs.gov/irb/2016-01_IRB/ar14.html.    In determining whether to grant a waiver, the IRS will consider all relevant facts and circumstances, including: Whether errors were made by the financial institution (other than      those described under Automatic waiver , earlier); Whether you were unable to complete the rollover due to death, disability, hospitalization, incarceration, restrictions imposed by a      foreign country, or postal error; Whether you used the amount distributed (for example, in the case of payment by check, whether you cashed the check); and How much time has passed since the date of distribution. You can also see if you can get ETrade to ""recharacterize"" the equity position to your desired target IRA.  The positive here is that the allowed decision window for calendar year 2016 rollovers is October 15 2017; the negatives are this is irrevocable, and restricts certain distributions from the target for a year (unlikely to impact your situation, but, you know, ""trust but verify"" anonymous internet advice); and it requires ETrade to recognize the original transaction was a rollover to a Roth IRA, which they currently don't.  But if their system lets them put it through you could end up with the amount in a traditional IRA with no other taxable events to report, which appears to be your goal.   Recharacterization FAQ" "Assuming these are standardized and regulated contracts, the short answer is yes.  In your example, Trader A is short while Trader B is long.  If Trader B wants to exit his long position, he merely enters a ""sell to close"" order with his broker. Trader B never goes short as you state.  He was long while he held the contract, then he ""sold to close"". As to who finds the buyer of Trader B's contract, I believe that would be the exchange or a market maker.  Therefore, Trader C ends up the counterparty to Trader A's short position after buying from Trader B.  Assuming the contract is held until expiration, Trader A is responsible for delivering contracted product to Trader C for contracted price.  In reality this is generally settled up in cash, and Trader A and Trader C never even know each other's identity." Check the employee-friends-and-family sales contract, which your friend should be able to get quite easily. There is almost always a minimum holding period before resale clause, specifically to prevent this kind of scenario. Without that clause, the dealers tend to riot... Also, remember that a car loses a huge percentage of its value the moment it leaves the lot. Odds are that you'd be doing well to find someone willing to buy it from you at the discounted price. If you don't want this car, ask your friend not to buy it and get one you do want. Seriously. "Is this legal? Why not? But you might have trouble deducting losses on your taxes, especially if you sell to someone related to you in some way (which is indeed what you're doing). See the added portion below regarding dealing with ""related person"" (which a sibling is). The state of Maryland has a transfer/recordation tax of 1.5% for each, the buyer and seller. Would this be computed on the appraised or sale value? You should check with the State. In California property taxes are assessed based on sale value, but if the sale value is bogus the assessors have the right to recalculate. Since you're selling to family, the assessors will likely to intervene and set a more close to ""fair market"" value on the transaction, but again - check the local law. Will this pose any problem if the buyer needs financing? Likely, banks will be suspicious.Since you're giving a discount to your sibling, it will likely not cause a problem for financing. If it was an unrelated person getting such a discount, it would likely to have raised some questions. Would I be able to deduct a capital loss on my tax return? As I said - it may be a problem. If the transaction is between related people - likely not. Otherwise - not sure. Check with a professional tax adviser (EA or CPA licensed in Maryland). You mentioned in the comment that the buyer is a sibling. IRS Publication 544 has a list of what is considered ""related person"", and that includes siblings. So the short answer is NO, you will not be able to deduct the loss. The tax treatment is not trivial in this case, and I suggest to have a professional tax adviser guide you on how to proceed. Here's the definition of ""related person"" from the IRS pub. 544: Members of a family, including only brothers, sisters, half-brothers, half-sisters, spouse, ancestors (parents, grandparents,   etc.), and lineal descendants (children, grandchildren, etc.). An individual and a corporation if the individual directly or indirectly owns more than 50% in value of the outstanding stock of the   corporation. Two corporations that are members of the same controlled group as defined in section 267(f) of the Internal Revenue Code. A trust fiduciary and a corporation if the trust or the grantor of the trust directly or indirectly owns more than 50% in value of the   outstanding stock of the corporation. A grantor and fiduciary, and the fiduciary and beneficiary, of any trust. Fiduciaries of two different trusts, and the fiduciary and beneficiary of two different trusts, if the same person is the grantor   of both trusts. A tax-exempt educational or charitable organization and a person who directly or indirectly controls the organization, or a member of   that person's family. A corporation and a partnership if the same persons own more than 50% in value of the outstanding stock of the corporation and more than   50% of the capital interest or profits interest in the partnership. Two S corporations if the same persons own more than 50% in value of the outstanding stock of each corporation. Two corporations, one of which is an S corporation, if the same persons own more than 50% in value of the outstanding stock of each   corporation. An executor and a beneficiary of an estate unless the sale or exchange is in satisfaction of a pecuniary bequest. Two partnerships if the same persons directly or indirectly own more than 50% of the capital interests or profits interests in both   partnerships. A person and a partnership if the person directly or indirectly owns more than 50% of the capital interest or profits interest in the   partnership."