How to know if two ETFs are 'substantially identical' according to wash sale rules?
"It sounds like this is an entirely unsettled question, unfortunately.  In the examples you provide, I think it is safe to say that none of those are 'substantially identical'; a small overlap or no overlap certainly should not be considered such by a reasonable interpretation of the rule. This article on Kitces goes into some detail on the topic.  A few specifics. First, Former publication 564 explains: Ordinarily, shares issued by one mutual fund are not considered to be substantially identical to shares issued by another mutual fund. Of course, what ""ordinarily"" means is unspecified (and this is no longer a current publication, so, who knows). The Kitces article goes on to explain that the IRS hasn't really gone after wash sales for mutual funds: Over the years, the IRS has not pursued wash sale abuses against mutual funds, perhaps because it just wasn’t very feasible to crack down on them, or perhaps because it just wasn’t perceived as that big of an abuse. After all, while the rules might allow you to loss-harvest a particular stock you couldn’t have otherwise, it also limits you from harvesting ANY losses if the overall fund is up in the aggregate, since losses on individual stocks can’t pass through to the mutual fund shareholders. But then goes to explain about ETFs being very different: sell SPY, buy IVV or VTI, and you're basically buying/selling the identical thing (99% or so correlation in stocks owned).   The recommendation by the article is to look at the correlation in owned stocks, and stay away from things over 95%; that seems reasonable in my book as well. Ultimately, there will no doubt be a large number of “grey” and murky situations, but I suspect that until the IRS provides better guidance (or Congress rewrites/updates the wash sale rules altogether!), in the near term the easiest “red flag” warning is simply to look at the correlation between the original investment being loss-harvested, and the replacement security; at correlations above 0.95, and especially at 0.99+, it’s difficult to argue that the securities are not ”substantially identical” to each other in performance. Basically - use common sense, and don't do anything you think would be hard to defend in an audit, but otherwise you should be okay." "Nobody knows for sure what ""substantially identical"" means because the IRS hasn't officially defined it. Until they do so, it would come down to the decision of an auditor or a tax court. The rule of thumb that I have always heard is if the funds track the same index, they are probably substantially identical. I think most people wouldn't consider any pair of AGG, CMF, and NYF to be substantially identical, so you should be safe with your tax-loss harvesting strategy."
I realize this is a dated question, but for anyone interested in this subject please be aware of the availability of IRC § 1235 and capital gain treatment for the sale of patents.  When the holder of a patent transfers all substantial rights to an unrelated person, it can qualify for long-term capital gain treatment.  That can be a meaningful tax savings relative to ordinary income treatment. There are a number of specific provisions and requirements to access § 1235.  The holder must be the creator or someone unrelated (and not the creator's employer) who purchased the patent from the creator.  The holder must transfer all substantial rights to the patent (not a licensing), or sell an undivided portion of all substantial rights (partial sale, again not a license).  The benefit of § 1235 is that long-term treatment will apply even for patents with holding periods under 1 year.  Other rules and permutations of course also apply.  Those who fail § 1235 may still qualify their assets as capital under § 1221 or § 1231.  A patent held by its creator will often qualify as a capital asset. It may not make any sense to sell your business as a whole, particularly if all a purchaser wants is a patent or group of patents.  Of course, if the patent was held by its creator in a single-member LLC or other disregarded entity sold to a buyer, then the tax treatment is still treated as the sale of a long-term capital asset. What JoeTaxpayer means is that you can sell one ETF and buy another that will perform substantially the same during the 30 day wash sale period without being considered substantially the same from a wash sale perspective more easily than you could with an individual stock. For example, you could sell an S&P 500 index ETF and then temporarily buy a DJIA index ETF. As these track different indexes, they are not considered to be substantially the same for wash sale purposes, but for a short term investing period, their performance should still be substantially the same. Yes. As long as the stock is in a taxable account (i.e. not a tax deferred retirement account) you'll pay gain on the profit regardless of subsequent purchases.  If the sale is a loss, however, you'll risk delaying the claim for the loss if you repurchase identical shares within 30 days of that sale. This is called a wash sale. The best way to save on clothes is up to you.  I have friends who save all year for two yearly shopping trips to update anything that may need updating at the time.  By allowing themselves only two trips, they control the money spent.  Bring it in cash and stop buying when you run out. On the other hand in my family we shop sales.  When we determine that we need something we wait until we find a sale.  When we see an exceptionally good sale on something we know we will need (basic work dress shoes, for example), we'll purchase it and save it until the existing item it is replacing has worn out.  Our strategy is to know what we need and buy it when the price is right.  We tend to wait on anything that isn't on sale until we can find the right item at a price we like, which sometimes means stretching the existing piece of clothing it is replacing until well after its prime. If you've got a list you're shopping from, you know what you need.  The question becomes: how will you control your spending best?  Carefully shopping sales and using coupons, or budgeting for a spree within limits? "This is the sad state of US stock markets and Regulation T. Yes, while options have cleared & settled for t+1 (trade +1 day) for years and now actually clear ""instantly"" on some exchanges, stocks still clear & settle in t+3.  There really is no excuse for it. If you are in a margin account, regulations permit the trading of unsettled funds without affecting margin requirements, so your funds in effect are available immediately after trading but aren't considered margin loans.  Some strict brokers will even restrict the amount of uncleared margin funds you can trade with (Scottrade used to be hyper safe and was the only online discount broker that did this years ago); others will allow you to withdraw a large percentage of your funds immediately (I think E*Trade lets you withdraw up to 90% of unsettled funds immediately). If you are in a cash account, you are authorized to buy with unsettled funds, but you can't sell purchases made on unsettled funds until such funds clear, or you'll be barred for 90 days from trading as your letter threatened; besides, most brokers don't allow this.  You certainly aren't allowed to withdraw unsettled funds (by your broker) in such an account as it would technically constitute a loan for which you aren't even liable since you've agreed to no loan contract, a margin agreement.  I can't be sure if that actually violates Reg T, but when I am, I'll edit. While it is true that all marketable options are cleared through one central entity, the Options Clearing Corporation, with stocks, clearing & settling still occurs between brokers, netting their transactions between each other electronically. All financial products could clear & settle immediately imo, and I'd rather not start a firestorm by giving my opinion why not. Don't even get me started on the bond market... As to the actual process, it's called ""clearing & settling"". The general process (which can generally be applied to all financial instruments from cash deposits to derivatives trading) is: The reason why all of the old financial companies were grouped on Wall St. is because they'd have runners physically carting all of the certificates from building to building.  Then, they discovered netting so slowed down the process to balance the accounts and only cart the net amounts of certificates they owed each other.  This is how we get the term ""bankers hours"" where financial firms would close to the public early to account for the days trading.  While this is all really done instantly behind your back at your broker, they've conveniently kept the short hours." No, this is not generally possible, as each security purchase is booked as a separate order => hence separate transaction. You can do this through purchasing of a fund, i.e.: purchasing one share of a ETF will get you a relative share of the ETF holdings, but the actual holdings are not up to you then. "When there is a trade the shares were both bought and sold. In any trade on the secondary market there has to be both a buyer and a seller for the trade to take place. So in ""lasttradesize"" a buyer has bought the shares from a seller." "You quickly run into issues of what denotes ""similar"", and how to construct an appropriate index methodology. For example, do you group all CB arb funds together globally or separate them by country? Is long-bias equity long-short different to no-bias and variable-bias? Is a fund that concentrates on sovereign debt more like a macro fund or a fixed income fund? And so on. By definition, hedge funds try not to mimic their peers, with varying degrees of success.  Even if you get through that problem, how do you create the index? You may not be able to get return numbers for all the ""similar"" funds, and even if you do, how do you weight them? By AUM, or equal weight?  There are commercial indices out there (CSFB, Eurekahedge, Marhedge, Barclays, MSCI, etc) but there's no one accepted standard, and it's unlikely that there ever will be as a result. It's certainly interesting to look at your performance versus one of these indices, and many investors do monitor fund performance this way, but to demand strict benchmarking to one of them is a big ask..."