Unlocking the Mystery of Capital Gains Taxes (Including the Wash Sale Rule)

June 06, 2025

Understanding capital gains and losses is important for managing investments and taxes. The IRS says almost everything you own and use for personal or investment reasons is a capital asset, like your home, stocks, and bonds. When you sell any of these, you either make a profit (a gain) or lose money (a loss). Profits and losses may increase or decrease the amount of tax you owe, depending on how long you’ve owned the asset.

Capital gains and losses can affect how much tax you pay in the year you sell your assets, but remember, if you sell personal things like your home or car, you can’t use those losses to lower your tax bill. For now, let’s focus on investments.

Short-term or long-term

There are two types of gains and losses: short-term and long-term. If you’ve owned something for one year or less, it’s considered short term. If you hold on to it for more than one year, it’s considered long term. This matters for tax purposes because short-term and long-term gains have different tax rates. Keep this in mind when selling investments in a taxable, non-qualified brokerage account.

How the sale of an investment is taxed

Here’s how to figure out how your investments will be taxed:

First, calculate gains and losses on assets you’ve held for one year or less (i.e., short-term assets). To determine a gain or loss, take the proceeds from the sale of each asset and subtract the amount you paid for it (i.e., its cost basis). The result is either a gain or a loss. Subtract short-term losses from short-term gains to find your net short-term gain or loss.

Next, calculate gains and losses on assets you’ve held for more than one year (i.e., long-term assets) using the same process. Subtract long-term losses from long-term gains to find your net long-term gain or loss.

If you have a net long-term gain and a net short-term loss: Subtract your short-term loss from your long-term gain to get your “net capital gain or loss.” Long-term gains are taxed at lower rates than your income. The rate can be 0%,15%, or 20% depending on your income. There may also be an extra 3.8% Medicare surtax. State tax rates can be different, so check with your local tax office.

If you have a net short-term gain and a net long-term loss: Subtract the long-term loss from the short-term gain. Any remaining gain will be taxed at your tax bracket based on your income level.

If you have both a net short-term gain and a net long-term gain: The short-term gain will be taxed at your regular income rate, while the long-term gain will have its own lower rates.

If you have a net loss, you can subtract up to $3,000 of losses from your other income on your tax return. If you have more losses, you can use them in future years.

The Wash Sale Rule

Lastly, there’s a rule called the wash sale rule. If you buy back the same investment (or one very similar) within 30 days before or after selling it, you cannot claim a loss on your tax return for that sale. You can, however, add the loss to the cost of the repurchased investment and benefit from the loss down the road when you sell that investment. Capital gains taxes can be tricky, but a tax professional can help you understand them better. To learn more, check out IRS Tax Topic 409, Capital gains and losses.

How are Restricted Stock Units (RSUs) Taxed?

June 06, 2025

Restricted Stock Units (RSUs) are a form of equity compensation. They are awarded as company stock and can be viewed as part of an employee’s overall compensation package. How this form of compensation is taxed can be tricky, so it is important to know the ins and outs so that there are no surprises come tax time.

RSU Basics

RSUs are typically awarded when an employee starts their job and/or on a regular basis at the discretion of the employer. When RSUs are awarded, the employee does not own them yet. Ownership comes according to a predetermined timetable known as a vesting schedule. For example, an award of 1,600 shares may vest 100 shares per quarter for the next 16 quarters (four years). As shares vest, employees can sell the shares as needed to generate cash. The selling of shares may be subject to restricted trading windows, so employees should check with their employer on that. Here is a breakdown of when and how employees are taxed on RSUs:

Taxation At the Time of Award

Unless your RSUs are immediately vested, they are generally not taxed at this time.

Taxation At the Time of Vesting

The vesting of your shares is a taxable event. The value of the shares that vest is taxed as ordinary income in the year that the vesting occurs, even if you don’t sell the shares. For example, if 100 shares vest on May 15th and the value per share is $50, $5,000 (100 shares x $50 per share) will be added as taxable income for the year.

The amount of federal taxes owed depends on your tax bracket which is determined by your overall tax situation for the year. Depending on your state of residence, state and local taxes may be owed as well. Note that the employer may automatically sell a certain amount of shares to be used for tax withholding at the federal and state levels, if applicable. Check with your employer to see if the number of shares sold for withholding can be changed to reflect your anticipated overall tax situation.

Taxation At the Time of Sale

The sale of vested RSUs is a taxable event as well. You will have to pay capital gains tax on any appreciation of the value of the stock from the time of vesting to the time of sale. Building on the example above, if the 100 shares are later sold for $60 per share (a total value of $6,000), you will owe capital gains tax on the $1,000 of appreciation (i.e., $6,000 sale value – $5,000 cost basis).

There are two types of capital gains:

Short-term capital gain. If the time between vesting and selling is one year or less, it will be a short-term capital gain and taxed as ordinary income for the year. 

Long-term capital gain. If the time between vesting and selling is more than one year, it will be considered a long-term capital gain and will be subject to long-term capital gains tax rates

Generally, less taxes are owed with a long-term capital gain, but you should always compare short- and long-term gains to identify which sales would reduce tax liability most effectively. If the value of the shares when sold is less than the value when they vested, this will incur a capital loss that may be used to offset capital gains in the same year (but be aware of the wash sale rule).

Pro Tip: If you don’t intend to hold on to them very long, consider selling shares that vest immediately to minimize taxes.

If you are fortunate enough to receive RSUs as a form of stock compensation, it’s important to understand how they are taxed as part of an overall tax planning strategy. As with many tax matters, it’s a good idea to consult with a tax professional to get advice on your specific tax situation.

Workplace Financial Wellness Programs: Frequently Asked Questions

February 08, 2017

Liz Davidson, founder and CEO of Financial Finesse, answers some of the most common questions about workplace financial wellness programs, such as how to have an impact on every employee generation present in the workforce; where fintech tools fit into your program; how to decipher between financial wellness programs and financial education programs; and more.

Workplace Financial Wellness Programs: Best Practices Guide

February 08, 2017

Our best practices guide for workplace financial wellness programs defines what it means to be financially well, and what constitutes a workplace financial wellness program to help employers avoid ‘bait and switch’ providers who are marketing themselves as financial wellness providers when in reality, they are aiming to sell employees a financial product or service. This guide aims to set industry standards around financial wellness programs in the workplace.

Integrating Employee Benefits Into Workplace Financial Wellness

October 24, 2016

Employees Say Benefits Drive Their Engagement with Their Employer, But The Vast Majority Don’t Maximize The Benefits They Have

Employees who understand, maximize and appreciate the value of their employee benefits are happier at work and more productive and engaged.  This isn’t just a guess  — the research agrees. Per SHRM’s 2016 Employee Job Satisfaction and Engagement Survey, 84 percent of employees indicated that their benefits were critical to their financial wellbeing, and 60 percent said that benefit were a key factor in their decision to join or stay at a company. Yet, most admit not fully understanding the benefits they have and virtually all are not fully maximizing them— accidentally leaving money on the table each year, not even realizing it. Based on our own research working with hundreds of thousands of employees over the years, many are leaving upwards of a million dollars on the table by not maximizing the benefits they have — and instead using that money for “nice to have” purchases that decline in value or going outside their employer to invest in more expensive financial products and services which often don’t have the same tax advantages. In some cases, employees are actually paying out of pocket for benefits the company would otherwise fully or partially subsidize, such as gym memberships, daycare, commuter benefits, legal support, tuition or continuing education reimbursement or relocation expenses. The list goes on.

Even Benefits Managers Don’t Understand Their Entire Benefit Offering

When we work with benefits managers to integrate all employee benefits into their financial wellness program, the most common refrain we hear is, “I didn’t know we had that benefit!”  If that’s sometimes the sentiment of those who manage benefits for a living, imagine how employees in the field must feel. Imagine how differently they might feel if they knew all the company was providing them and could take full advantage of every benefit that truly provided a benefit to them personally.

Because of this disconnect, it is absolutely critical your workforce financial wellness program should integrate all benefits so that employees recognize their benefits are a critical part of their financial wellness and have guidance as to how to maximize them as part of their overall financial plan. This helps employees understand where to go to find resources and the role each benefit plays in their financial lives.

It also should be used as the key vehicle to help employees manage benefits changes, so they minimize the impact to their finances and even manage to find ways to make the change work to their advantage.

The Most Successful Employers Offer Employees Unlimited Personalized Guidance On Their Benefits

The most successful benefits planning programs — which help employees maximize their benefits based on their own personal financial situation — employ a “concierge” strategy where the employee has access, both online, through a mobile app, over the phone, and in person, to their own personal financial coach who can help them make the right decisions for their life situation and goals.  As a best practice to reach a large number of employees in a deeply personalized the coaching should meet the following criteria:

  1.  The coaching should be delivered by a separate vendor not one of your benefits providers. The vendor you choose should be free from any conflicts of interests associated with employees using certain benefits over others. In addition, the vendor should have deep financial planning expertise as well as a long track record for helping employees integrate benefits into their overall financial plans. In other words, their core business should be centered on providing this kind of personal guidance around benefits, entirely customized to each of their client’s specific benefits offerings. With the complexity of benefits these days, it’s not enough to have someone who specializes in one or two benefits; the reality is that each employee has different financial needs and any coach they work with needs to help them identify and effectively manage all the benefits that meet their needs.
  2. The company you retain for the coaching should not provide financial advice or sell financial services — both have serious legal risks to the company and potentially to you personally (if you are part of the investment committee who oversees the retirement plan,  for example). Guidance is the sweet spot here. The right partner will guide employees and work with them to develop the right strategy, not make decisions for them.  The result is better for employees; they learn how valuable their benefits really are and go into all decisions fully informed of the pros and cons. Not to mention, they gain knowledge to become more adept at managing their benefits over time.
  3. The company should be familiar with ALL benefits you have available—not just retirement or health, but all voluntary benefits, all work-life benefits, all perks, and all tools, resources, apps, and vendors who provide any sort of education or communication around the benefits. Without this knowledge, you only solve part of the problem and employees lose out on key benefits that could be life changing based on their specific needs.

Managing Benefits Changes

Benefits changes are a fact of life today, whether they are for cost-savings reasons, to add more value, flexibility or support to employees, or simply to simplify or streamline a benefits offering to make it easier for employees to manage. Unfortunately, even good changes can add yet another thing for an employee to understand and act upon, and most major changes transition more costs to employees, adding to their financial stress.

If you handle benefits planning through the process described above, benefits changes become much easier to manage, because employees automatically have a coach to turn to in order to make the right decisions for their situation.

However, in virtually all cases, best in class employers do more than simply leverage their existing coaching. Without broad-based communications and education around the changes, and multiple touch points to ensure that all employees affected are aware of the change, it’s easy for important decisions to “fall through the cracks.”  Your financial wellness provider should help you proactively communicate and educate employees around all changes —consulting around all aspects of the change management process, producing materials, videos, and tools as needed to help employees navigate the change, and delivering webcasts and workshops to all those affected by the change. They should also provide you with full reporting of employee engagement in these different communications and education campaigns, both for legal documentation but also so you understand what type of communication resonated the most for the purpose of designing future campaigns.

Among the most common changes that require this level of communication and education–

  • Changing healthcare plan to a HDHP and HSA;
  • Compensation changes;
  • Offering early retirement or another severance program;
  • Terminating or freezing a benefit, such as a defined benefit plan or retiree health; and
  • Integrating employee benefit communications after a merger or acquisition.

One last note

Benefits and personal finances are complicated and highly personal. Beware of any vendor who presents a one size fits all solution that is “turnkey” and “highly scalable”. While their solution may fit into part of a larger strategy, they are typically not set up to provide the level of customization you need to address either employee benefits planning or communication of benefits changes. Your employees care much more about their financial security than any singular benefit you provide. Your ability to bridge the gap between the myriad of benefits and the strategy they need to employ to become financially secure by maximizing these benefits is what matters most. The days of siloed benefits offerings and floods of email announcements on different benefits options are over. It’s now about what it always should have been — the employee who you want to benefit in the first place.

Don’t Leave Any Money On The Way Out

October 06, 2015

I was recently talking to a dear friend of mine who just lost her job due to a layoff. She was shell-shocked, scared and not sure what to do. As I listened to her talk about her plan, I asked her about her workplace benefits and she said that she got the package, saw no value in anything she had and was getting ready to throw the package away. Continue reading “Don’t Leave Any Money On The Way Out”

Are You Ready for National Payroll Week?

September 04, 2012

Now that we’re all back to work after celebrating Labor Day, don’t let the fun stop – continue the celebration by recognizing National Payroll Week(NPW) at work. This special week celebrates the economic, cultural, and social achievements of workers and the significance of “an honest day’s work for an honest day’s pay.”  Started in 1996 by the American Payroll Association, NPW is a national campaign to help America’s workers understand more about their paychecks, the payroll withholding system and other payroll-driven benefits.  Shining a spotlight on employees’ paychecks is a great way to transition to your upcoming open enrollment by getting your workforce already starting to think about their paycheck and current deductions.  Continue reading “Are You Ready for National Payroll Week?”

Making Your Benefits Communications Oscar-Worthy

February 28, 2012

The Oscar awards were on TV this past Sunday but since there were no actors I was rooting for, my husband decided we were going to rent a movie so he picked Tower Heist, which after watching it I can say is definitely not worthy of an Oscar.  So what does Tower Heist have to do with benefits communication? Continue reading “Making Your Benefits Communications Oscar-Worthy”

What It Takes to Have a Winning Benefits Communications Plan for Your Employees

October 25, 2011

Congratulations to the most recent PSCA Signature Award Winners for 2011!  The Profit Sharing/401(k) Council of America (PSCA) announced the winners of their Signature Awards at a special presentation at its 64th Annual National Conference at The Mirage in Las Vegas last month, to honor excellence in plan communication and education.  This year, the Signature Award judges recognized 48 winners in 18 categories, based on how companies design, manage, and provide defined contribution communication and investment education to plan participants.  Signature Award judges carefully review how effective the campaign was at achieving its goals and I’m proud to say that 3 employers that I have worked closely with over the past few years, were recognized as 2011 Signature Award Winners. Continue reading “What It Takes to Have a Winning Benefits Communications Plan for Your Employees”

Roll Call: 24th Annual Benefits Forum and Expo 9/25 to 9/27

September 20, 2011

Employee Benefit News’ Benefits Forum and Expo is the largest event in the nation solely dedicated to employee benefits, so are you planning on attending?  If so, you’ll be among many senior benefits professionals who will be traveling to Dallas, TX next week.  I won’t be there myself, but make sure to look for the Financial Wellness at Work track on the conference agenda, which kicks off the day on Sunday, September 25th. Continue reading “Roll Call: 24th Annual Benefits Forum and Expo 9/25 to 9/27”

Financial Education in the Workplace: What a Difference a Few Years Make

January 04, 2011

I recently spent a few cold, snowy days meeting with employees in the Midwest counseling each of them regarding their retirement goals.  I was surprised to hear quite a few employees were planning on early retirement, especially since we hear the trend is just the opposite because of our current economy.  Continue reading “Financial Education in the Workplace: What a Difference a Few Years Make”