Tax Loss Harvesting with Vanguard: A Step by Step Guide
- What?!? I just lost 10% of my net worth. This is horrible!
- Meh. A 10% market correction happens in most years. It will bounce back. Eventually.
- Cool! Let’s see what I can tax loss harvest.
Over the last ten days, the market experienced a 10% correction for the first time in some time. While seeing several years’ worth of spending erased from our balance sheet was less than awesome, I mostly shrugged it off. I’m always looking for a silver lining, and I found one in not only having the ability to tax loss harvest a recent investment, but also to have the opportunity to capture those screenshots to share in this educational post.
I have previously written about how I used tax loss harvesting to Brofit from the Brexit, but this is the first time I had the forethought to save the images each step of the way.
Tax Loss Harvesting Basics
What is tax loss harvesting (TLH)?
TLH is a way to capture a “paper loss” by selling an asset that has declined in value and subsequently purchasing a similar asset to avoid locking in an actual loss. This only works in a taxable brokerage account. In tax-advantaged retirement accounts, there are no tax implications when buying and selling within the account.
The amount of the loss can be deducted from ordinary income when you file your income taxes, up to $3,000 per year, resulting in savings of $1,000 or more for the typical high-income professional. If Uncle Sam is willing to give me $1,000 or more per year for deciding to swap some shares of a Total Stock Market Fund for the S&P 500 index every once in awhile, I’ll gladly take them up on that offer time and time again.
If “paper losses” exceed $3,000 in any given year, the excess losses can be carried over to subsequent years. In 2016, a year in which the market actually saw a double-digit gain, I tallied over $45,000 in losses early in the year, giving me over 15 years worth of $3,000 deductions from 2016 alone.
A handful of timely transactions in prior years have saved me thousands of dollars already (I also harvested about $30,000 in losses in 2015), and those savings have the potential to continue to save me $1,000 or so per year for decades as long as my income keeps me in the upper tax brackets.
What are Tax Loss Harvesting Partners?
TLH partners are assets that are similar (have a high correlation) but are not “substantially identical.” That last phrase belongs to the IRS, and it hasn’t been defined precisely, but conventional wisdom is that a fund following a different index is different enough.
Funds that follow the same index, but are offered by different companies (i.e. Scwab’s SWTSX & Fidelity’s FSTVX, both total stock market funds) would be considered by most to be substantially identical, and are not a wise choice as partners.
Likewise, I would not consider the ETF version of the mutual fund you’re selling at a loss (or vice versa). Look for assets that are following different indices.
Interestingly, as pointed out in the comments, Vanguard’s VTSAX follows a different total stock market index, and it may be a suitable TLH partner to the Schwab and Fidelity funds. Personally, it’s close enough to a gray area that I would hesitate to make such a swap, but it’s probably just fine.
A good partner is not only a bit different, but also one you would not mind holding indefinitely. If you’re going to exchange or trade into the fund, you should be comfortable with that asset rising in value and remaining in your account for years.
A fund with a substantially higher expense ratio would be a poor choice. I would also advise against trading a tax-efficient passive index fund for an actively managed fund that might spin off excessive capital gains. The tax consequences of holding such a fund long-term could negate the benefit of the tax loss harvesting.
The following are some decent trading partners. I use Vanguard mutual funds, but you should be able to find similar partners in mutual fund or ETF form from your favored broker, be it Fidelity, Schwab, iShares, or whomever.
- Total Stock Market / S&P 500 / Large Cap Index
- Total International / All-World Ex-US / Developed Market
- Small Cap Index / Mid Cap Index / Extended Market
I’ve only traded in the first two categories, as I keep my small and mid cap funds in tax-advantaged accounts. I have gone one step further in the international category, trading developed markets for European and Pacific indexes. Frankly, I was happy to see those drop further so I could jump back into a total international fund later on, so I wouldn’t necessarily recommend such a move, as it violates the principle I mentioned above about only exchanging into funds you’d be comfortable owning forever.
Of course, if you’re feeling charitable, you could always donate unwanted funds to a donor advised fund if they do experience significant gains.
You could also look at harvesting losses in municipal bond funds (you shouldn’t hold tax-inefficient non-muni bond funds in taxable), but those don’t experience the wild price swings that stocks do, so it’s unlikely you’d see meaningful opportunities to harvest sizable losses with bonds unless you have a huge bond balance.
Tax Loss Harvesting Dangers
Perhaps danger is a strong word, but there are plenty of ways to screw this up, which is why many investors don’t bother with it or rely on a roboadvisor’s algorithm to do the tax loss harvesting for them. But really, the worst you can do is negate the tax benefit of your efforts, and most mishaps only partially reduce the amount of the loss you’lltake (assuming you choose to report the mistake).
What you want to avoid in the 30-day window before and after tax loss harvesting is a wash sale. A wash sale is a purchase of identical or “substantially identical” replacement shares of an asset you sold at a loss during that 60-day (30 days before and 30 days after) timeframe.
You also want to be sure your cost basis determination is not set to First In First Out or Average Cost in your taxable account. You want each lot to be recorded with the purchase price, and you want the ability to sell each purchased lot individually.
With Vanguard, you do this by selecting Specific Identification (SpecId) as your cost basis for all funds held in a taxable account.
I suppose another “danger” is missing an opportunity to TLH. Waiting for a loss to get bigger can be a fool’s errand. It makes sense to have a threshold dollar amount at which you’ll consider harvesting a loss. Perhaps it’s $500 or $1,000. Once that threshold is crossed, I would seize the opportunity. If the asset class continues to drop, you can TLH again into a third partner within 30 days, or back into your original position beyond 30 days.
How to Avoid a Wash Sale
The simple answer is to avoid buying replacement shares a month before and after tax loss harvesting. It sounds simple enough, but there are several ways to unwittingly foul this up.
The most likely way to inadvertently create a wash sale is with automated new investments and automated dividend reinvestments. Let’s look at each of these individually.
Automated investments often take place in a tax-advantaged account like a 401(k), 403(b), 457(b), or SEP or SIMPLE IRA. While investments in these accounts may not be noticed by your taxable brokerage account or the IRS, it’s best to avoid any gray areas, even if the impetus to report them may be on you.
How do you avoid automatically investing into a substantially identical asset in a tax-advantaged account shortly before or after tax loss harvesting in a taxable account?
The simplest way is by investing in different asset classes in your tax-advantaged accounts.
I accomplish this by investing in small cap, mid cap, and emerging market stock indices in my tax-advantaged accounts, while investing in large cap and total international / developed markets in taxable. See my portfolio for full details.
Such a strategy doesn’t jive well with a simpler three-fund portfolio, but I feel the benefits of tax loss harvesting outweigh the benefits of simplicity. I also like optimizing, even if it’s at the expense of simplifying.
How do you avoid reinvesting into a substantially identical asset class after tax loss harvesting?
This is straightforward. Avoid automatically reinvesting your dividends. Manually reinvest them four times a year (or however often your receive dividends).
I have my taxable mutual funds set up to send all dividends to a Vanguard money market fund. In the fourth week of March, June, September, and December, I manually reinvest the dividends. If I have recently taken advantage of a tax loss harvesting opportunity, I don’t buy into the fund I just sold.
If you’re afraid you won’t notice the dividends hit your money market fund, have them sent to your checking account where you’ll be more likely to see them, and reinvest from there.
If you do accidentally goof this up and create a wash sale, it’s not a huge deal. When you invest or reinvest into a fund that you sold at a loss within 30 days, you’re most likely purchasing a smaller amount than you sold.
For example, if you sell 100 shares at a loss and you automatically invested or reinvested in 10 shares, you can still take the loss on 90 of those 100 shares. This is known as a partial wash sale. If you purchase 100 or more substantially identical shares within the 30-day window before or after capturing a loss by selling 100 shares, the tax benefit of your efforts is indeed eliminated.
I have my investments set up in a way that a wash sale is very unlikely, but one of my favorite Bogleheads who goes by the moniker livesoft, the resident TLH guru, has intentionally created a wash sale as a public service. See his tutorial on what not to do, and how to file the appropriate tax forms if you do end up with a wash sale despite your best efforts.
Tax Loss Harvesting with Screenshots
So what does this look like in practice? Like I’ve done with my Backdoor Roth maneuvers, I took screenshots to make this as straightforward as possible.
Step 1: Recognize a loss has occurred
You can’t harvest a loss that you don’t know about. I track my investments with Personal Capital, and if you choose to do the same, you’ll help enhance this site’s charitable mission. I typically like to see a loss of at least $1,000, but TLH opportunities (for better or worse) have been hard to come by over the last couple years. When the market dropped a bunch after a recent investment, I pulled the trigger.
Note that I only held these shares for four trading days. Did I create a wash sale by selling shares of a mutual fund that I purchased a few days earlier, well within the 30-day window?
No! The shares I bought were not replacement shares for the ones I sold; they were the ones I sold. If I had bought two lots and only sold one lot, then I’d have issues, but as long as you sell all shares purchased in the last 30 days, you won’t create a wash sale.
Step 2: Select the lot(s) to sell or exchange
Using mutual funds, I don’t have to bother with a settlement fund, and there’s no downtime where my money is not invested. I simply exchange from one mutual fund to another, and the swap takes place at the end of the trading day.
In this case, my very recent $10,000 investment in Vanguard’s Total Market Stock Index (VTSAX) had lost a few hundred dollars in the first three trading days since I purchased the lot on February 2nd, and well into the fourth trading day, it was on track to lose a few hundred dollars more.
Taking advantage of this situation feels like being allowed to bet on the winner of a football game late in the fourth quarter when the home team’s up by three touchdowns. As long as the trade is entered before the market closes, the transaction will go through based on the closing price.
After logging into my taxable brokerage account at Vanguard, I click on “Exchange” in the fund that has a loss.
I am then presented with a list of lots purchased, along with the gains or losses in each. Only the most recently purchased lot has a loss, and I select it.
Step 3: Select the TLH Partner to Purchase
On the next screen, you’ll verify the fund you are selling on the left.
On the right, you’ll select the fund you’ll be purchasing with the proceeds of the sale you’re making at a loss. This will be your tax loss harvesting partner. If you don’t already own shares in the fund, you’ll be able to add it from this page. Each of the funds I own appear in the list, including my chosen TLH partner, the S&P 500 index fund.
Note that it looks like I’m only harvesting a loss of $283.37 ($10,000 – $9,716.63), but late in the trading day, the market was down another 4% or so, and I could count on a bigger loss barring a crazy last-minute Tom Brady-esque rally. Using ETFs, you could lock in the loss at the moment you choose to sell.
Step 4: Confirm the Tax Loss Harvest
After pressing continue, you’re done. At that moment, you’ll be presented with a confirmation.
The amount you’re selling from one fund and buying into another is based on the prior day’s closing price and is not representative of the final trade. Hence, the asterisk.
The next day, you can log in to see the true value of the paper loss you tax loss harvested.
The loss more than doubled in size from an estimated $283.37 to the actual $637.97. I had a pretty good idea this would be the case, as the stock market was down big late in the trading day when I set up this exchange.
A day or two later, I received a confirmation of the trade, which is essentially the same information you see above in a different format.
Under “Notes:” I am told that Vanguard won’t let me buy back into this fund in the next 30 days to comply with their frequent-trading policy. That’s a good thing — the last thing I want to do is buy more VTSAX and create a wash sale. Vanguard is protecting me from making a bonehead move, and I appreciate that.
Tax Loss Harvesting Summary
That’s all there is to it. Sell lot(s) that have lost money, buy something similar that’s not the same, and you’ll receive a 1099-B from your brokerage reporting a year’s worth of TLH efforts. Here’s an excerpt of my Vanguard 1099-B from 2016 showing a total of $45,449.15 in losses. Most were short-term losses, with the final $6,212.57 being a long-term loss.
As daunting as the concept may at first seem, tax loss harvesting is not a difficult task. I hope I’ve made the benefits clear and the process approachable.
Happy tax loss harvesting!