Don’t Let a Bonus or Stock Sale Catch You Off Guard at Tax Time
If your income changes during the year because of a bonus, stock sale, retirement distribution, or another large source of income, the tax impact can catch you by surprise if you wait until filing season to sort it out. The amount you owe and when you need to pay it depend on more than the size of the income increase.
Topics Discussed:
- How the 90% current-year and 100% or 110% prior-year safe harbor rules work
- When estimated tax payments are due and when payments may differ during the year
- How a bonus or stock sale can affect estimated tax requirements
- Why withholding is treated differently from estimated tax payments
- How retirement-account withholding may fit into year-end tax planning
- What information to gather before a fall tax-planning conversation with your CPA
Transcript:
Paul Sydlansky, CFP®:
Today I have with me Megan Hubbard, who is a CPA and partner at Mengel Metzger Barr. I’m excited to leverage Megan’s expertise as we talk about some of the common questions we get from clients around taxes.
Megan, thank you so much for joining us today. I appreciate it.
Megan Hubbard, CPA:
Absolutely.
Paul:
I have a list of questions that come up pretty often with clients. Fall is a time when we start looking at projections, taxes, and opportunities for things we may be able to do before year-end.
One topic that often comes up is the two safe harbors, the 90% current-year rule and the 100% or 110% prior-year rule.
Could you explain what those mean and how someone should think about them when they’re planning for the current year?
01:39 | Understanding the Two Safe Harbors
Megan:
Absolutely. When we talk about estimated taxes, there are basically two main safe harbors individuals can use to avoid an underpayment penalty.
The first is the 90% current-year safe harbor. During the year, you need to pay at least 90% of what your total tax liability will ultimately be for that year.
And when we say 90%, we’re talking about 90% of your tax, not 90% of your income. That’s an important distinction.
The challenge with that method is that you need a pretty good idea of what your income and tax liability will be for the year. That isn’t always easy depending on your sources of income.
Do you own a business? Is a lot of your income investment-related, where you aren’t sure exactly where things will end up?
The other option is the 100% or 110% prior-year safe harbor, which is often easier to work with.
Generally, you look at the total tax shown on last year’s tax return, which is a known number, and make sure you’ve paid at least the required amount during the current year through withholding or estimated tax payments.
The reason there are both 100% and 110% thresholds is that the requirement increases for higher-income taxpayers.
The higher-income threshold is based on the prior year’s adjusted gross income. That threshold is $150,000 for most taxpayers and $75,000 if you’re married filing separately.
Paul:
And that $150,000 is an income threshold, correct?
Megan:
Correct.
When you’re determining which safe harbor to use, if you have a client whose income fluctuates quite a bit from year to year, I usually look first at the prior-year safe harbor because we know exactly what that number is.
We know the prior-year tax, so we can determine what needs to be paid to meet that threshold.
03:35 | What the Safe Harbor Actually Does
It’s important to remember what a safe harbor does. It protects you from an estimated tax underpayment penalty.
It doesn’t mean you won’t owe additional tax when you file your return.
If your income increases significantly, you could still have a balance due when you file in April. The safe harbor simply means you prepaid enough during the year to avoid the estimated tax penalty.
There’s also a rule under which there generally isn’t an estimated tax penalty if the amount you owe after withholding and credits is less than $1,000.
Paul:
In a broad sense, what do those penalties look like? Are they based on a percentage of the amount that was underpaid, or is it a fixed dollar amount?
Megan:
It’s a percentage calculation. That’s something your accountant can work through with you.
There are clients who look at that penalty somewhat like paying interest to hold on to the money. There could be situations where someone wants to compare the underpayment penalty with what they could earn by keeping those funds available, but you need to look at the actual numbers and have someone help calculate it.
Paul:
That leads into my next question about estimated taxes.
For many of our clients who are salaried W-2 employees, withholding comes directly from their paycheck. But when someone becomes financially independent, owns a business, or starts receiving income from other sources, estimated taxes may become part of the picture.
Do estimated tax payments need to be equal every quarter? Can they be bunched together? What are the rules around the timing?
Megan:
In most cases, you’re going to be making four estimated tax payments during the year.
The standard deadlines are April 15, June 15, September 15, and January 15 of the following year. They don’t line up exactly with traditional calendar quarters.
Under the standard method of calculating estimates, you take the amount you’re required to pay for the year and divide it into four equal installments.
That doesn’t mean every taxpayer has to make four equal payments.
06:46 | Uneven Income and the Annualized Income Method
If someone’s income isn’t earned evenly throughout the year and there’s a large fluctuation, we can use what’s called the annualized income method.
That allows us to calculate the estimated tax requirement based more closely on when the income was actually earned.
That can be particularly helpful for someone who receives a large bonus, sells a large investment, or has another significant source of income later in the year. We don’t necessarily want to treat that income as though it was earned evenly throughout the entire year.
You also have to consider the cost and benefit of doing those additional calculations and potentially working with a CPA on them.
Some clients prefer the consistency of four equal payments, and that may make sense for them. It’s an individual calculation.
07:42 | When the Income Was Received
You also don’t have to make an estimated payment on the exact day you receive the income.
Under the annualized income method, income received during different portions of the year is associated with the applicable estimated payment period.
Withholding vs. Estimated Tax Payments
Another important distinction is the difference between withholding and estimated tax payments.
When we’re making sure enough tax has been paid during the year, federal withholding from W-2 compensation or a retirement distribution is generally treated as though it was paid evenly throughout the year, regardless of when it was actually withheld.
That can be a useful tax planning tool if you need additional withholding later in the year to address a shortfall.
Paul:
So with RMDs, for example, someone could theoretically wait until December, take the required distribution, and do a large amount of withholding at that point. The IRS may treat that withholding as though it occurred throughout the year.
Megan:
Correct.
That can be a useful planning strategy for retirees.
Let’s say you get to the end of the year and realize a retiree hasn’t had enough federal tax withheld or hasn’t made enough estimated payments.
If that person has a traditional IRA, one option could be to take a taxable IRA distribution in December and have a large amount of federal tax withheld from it.
It doesn’t necessarily have to correct a shortfall. Someone who is already taking an RMD could simply plan to handle withholding as part of that distribution.
10:09 | Consider the Tax Cost of the IRA Distribution
One thing to remember is that this strategy doesn’t reduce your tax. We’re using withholding as a tool for meeting the tax prepayment requirements.
We also need to consider the tax consequences of the IRA distribution itself.
With a traditional IRA, the distribution will normally generate taxable income. We don’t necessarily want to create unnecessary taxable income solely to generate withholding.
Tying the strategy to an RMD or another distribution the client already needs to take may make more sense.
You need to look at the full situation: the estimated tax requirements, taxability of the distributions, the person’s age, and the other factors involved.
Paul:
I think you answered this next question, but I want to ask it directly because we have many clients with executive compensation and company stock, whether that’s RSUs, options, or shares they’ve held for several years.
Let’s say we have a W-2 client earning $250,000 a year. In October, they sell stock and generate another $250,000, with $125,000 representing a long-term capital gain.
Does the tax on that gain need to be paid in that quarter, or could they potentially wait until they file the following April?
Megan:
It depends.
First, if someone sells stock at a gain, that gain is taxable in the year the stock is sold.
Then we look at the estimated tax rules to determine whether that gain creates an additional estimated tax requirement.
The timing matters. If you had a stock sale in April or May, for example, we would look at whether it affects the June payment.
12:49 | Start With the Safe Harbor
But we really want to go back to those safe harbor rules first.
Let’s say you have a very large stock gain, but when you look at your withholding and any estimated payments you’ve already made, you’ve paid enough to meet the applicable prior-year safe harbor.
In that case, you may have already paid in enough for estimated tax purposes.
An additional payment may not be required solely because of the stock sale.
You may still owe additional tax when you file your return, but if you’ve met the applicable safe harbor, you may be able to pay that balance at filing without an estimated tax underpayment penalty.
13:59 | How Rising Compensation Can Affect the Calculation
This is something we see with people who have executive compensation, RSUs, and company stock.
If someone’s salary has increased from the prior year, their withholding may also have increased.
In some cases, that withholding from compensation may already be enough to meet the applicable prior-year safe harbor.
But you also need to think about the following year. If you had a large capital gain this year, your prior-year tax number may be higher next year.
That can change the amount required to meet the safe harbor in the subsequent year.
Paul:
That’s a good point about salary increases.
Someone may think, “I’m making more income,” but they’re also withholding more. For the prior-year safe harbor, we’re focused on the tax number rather than simply looking at the increase in income.
Megan:
Correct.
We’re looking at the prior-year tax and determining whether enough has been paid to cover the applicable percentage of that amount.
The 90% current-year safe harbor is still available. It may come into play when income is lower or more predictable and we have a good idea of what the current-year tax liability will be.
But the prior-year safe harbor is often easier to calculate because we’re starting with a known number.
Paul:
One last question.
This is the time of year when we’re doing tax projections and thinking about potential year-end planning opportunities for clients.
Is there one thing you’d tell someone who is thinking about doing a projection? Is there information they can provide that makes the process more useful?
Megan:
My advice would be to start thinking about year-end planning in the fall.
Here in New York, when the leaves start changing, that’s a good reminder.
A lot of clients wait until December to have these conversations, and by then there’s less time to provide proactive guidance or consider different strategies.
17:23 | What to Bring to a Fall Tax Planning Meeting
I recommend getting into the habit of having a fall planning meeting with your CPA.
Bring things like your current-year pay stub showing year-to-date income and withholding, along with year-to-date investment information.
You can look at where things stand at the end of September, with three months remaining in the year, and ask: Am I on track? Have I paid enough? Do I need to pay more?
Maybe the answer is that you don’t need to make an additional payment.
Then you normally have another touchpoint with your CPA during tax season. At that point, your tax return gives you the prior-year tax number that can be used when planning estimated payments for the coming year.
18:13 | Keep Your CPA Updated When Something Changes
Between those meetings, reach out if something unexpected happens.
Maybe you receive a large bonus that wasn’t anticipated, sell stock, or begin taking distributions from a retirement account.
Proactive communication gives your CPA the information needed to help plan appropriately.
And in some cases, adequate withholding or your prior-year numbers may mean you don’t need to send in a large payment immediately.
Being able to coordinate with a CPA and someone in the financial planning world can be very helpful.
Paul:
My takeaway from that is: when the leaves turn, not when it starts snowing in upstate New York.
Megan:
That’s right.
Paul:
Because it can snow early here, too.
Megan, thank you so much for your time. This was fantastic and really helpful. We appreciate you joining us.
Megan:
Absolutely. Thank you.
Paul:
All right.
Lake Road Advisors (LRA) is a virtual wealth management firm headquartered in Corning, NY, with offices in Ithaca, NY, and Vancouver, WA. Founded by Paul Sydlansky, CFP®, in 2016, it serves successful couples planning their next chapter—whether that’s retirement, part-time work, or a less demanding second act. Paul has worked in the financial services industry for 25+ years. Prior to founding Lake Road Advisors, he worked at Morgan Stanley in Manhattan for 13 years, where he was a senior-level manager within the Institutional Equities Department. In 2018, he was named to Investopedia’s Top 100 Financial Advisors list. Paul received a Bachelor’s degree in Economics from Marist College and holds an MBA from New York University Leonard N. Stern School of Business. Paul is a CERTIFIED FINANCIAL PLANNER® and a member of the National Association of Personal Financial Advisors (NAPFA) and the XY Planning Network. They can be reached by phone at the Corning, NY office at (607) 463-8400, Ithaca, NY office at (607) 438-2914, or Vancouver, WA office at (607) 292-2172 or at the firm’s website at https://www.lakeroadadvisors.com/