Mid-Year Tax Checkup: 8 Things Worth Reviewing in June

Quick answer. A mid-year tax checkup is a 60-minute review run in June or early July with year-to-date paystubs, account statements, and last year’s return open on the desk. Eight areas are worth checking: withholding adequacy, estimated payments, retirement contributions, HSA pace, itemize-vs-standard projection, capital gains and losses, self-employment items, and life changes. The point is to surface questions while there are still six months to act. The Annual Tax Planner gives you the structure; this article gives you the questions.

April is too late for most tax adjustments. By the time the return is in front of you, the year is over. December is better, but narrow - one or two paychecks left, one shot at a retirement contribution before the calendar resets.

June leaves five to six months. Withholding can still be reshaped over twelve to fourteen paychecks. A 401(k) deferral percentage can be changed in a benefits portal in under a minute. The point of a mid-year checkup is not to file taxes early. It is to notice drift while there is room to act.

The eight items below each follow the same shape: what to check, how to check it in a spreadsheet, and what patterns are worth raising with a CPA. None of this replaces a tax professional on a complex year. It is the prep work that makes that meeting shorter.

What you need before starting

Five inputs.

If something is missing, run the review anyway. A blank cell is still information - it tells you which records to start keeping for the back half.

Withholding adequacy

What to check. Whether year-to-date federal withholding, run forward through December, will roughly cover the year’s projected tax liability.

How to check it in the spreadsheet. Pull federal tax withheld YTD from the latest paystub. Divide by pay periods elapsed, then multiply by total annual pay periods. Compare that projection against last year’s total federal tax from line 24 of the 1040.

Projected withholding = (YTD withheld / pay periods YTD) * pay periods in year
Gap                   = Line 24 of last year's 1040 - Projected withholding

A gap near zero means autopilot is roughly aligned. A large positive gap means projected withholding is short. A large negative gap means a refund is brewing - the IRS holds the money until April with no interest.

What to discuss with a CPA. If the gap is wide in either direction, whether the cause is structural (raise, new job, side income, dependent change) or seasonal (bonus timing, one-time event). The structural-vs-seasonal split is what determines whether a new Form W-4 is the right lever.

One caveat: changing withholding mid-year reshapes only the remaining paychecks. A W-4 submitted in July has about 13 paychecks to spread the correction across. The same correction filed in November has 4, which means a much larger per-check change. The IRS Tax Withholding Estimator handles the math and produces a completed W-4 to hand to payroll.

Estimated payments status

What to check. Whether Q1 (April 15) and Q2 (June 15) estimates were paid on time, and what Q3 (September 15) should look like.

How to check it in the spreadsheet. A row per quarter: due date, amount paid, payment date, confirmation number. Then the safe harbor reference:

Safe harbor target = Prior year total tax / 4
                   = Prior year total tax * 1.10 / 4  (if prior AGI > $150,000)

Per IRS guidance on the underpayment penalty, estimates avoid penalty if they total at least 90 percent of current-year tax or 100 percent of prior-year tax (110 percent when prior AGI exceeded $150,000), whichever is lower.

What to discuss with a CPA. If Q1 was missed, the underpayment penalty is already accruing - a CPA can quantify it and weigh catching up in Q3 against spreading the shortfall. If income is far above or below last year, the safe harbor floor still applies, but actual-income method may save cash flow. Our walkthrough on the quarterly estimated tax spreadsheet covers both methods.

Retirement contribution pace

What to check. YTD 401(k), 403(b), 457(b), or Solo 401(k) contributions against the 2026 IRS limit of $24,500, with $8,000 catch-up at age 50+ and an $11,250 super catch-up for ages 60 through 63. Traditional and Roth IRA contributions against the 2026 limit of $7,500 ($1,100 catch-up for 50+).

How to check it in the spreadsheet.

Remaining divided by months left is the monthly pace needed to hit each cap. The IRA deadline is April 15 of the following year, so the runway is longer.

The Roth IRA piece needs care. The 2026 Roth IRA phase-out runs $153,000 to $168,000 MAGI single, $242,000 to $252,000 married filing jointly (per IRS 2026 limits). MAGI is not gross income; it adds back several items. If income is near the threshold, a contribution that turns into an excess in April creates paperwork - it can be recharacterized or withdrawn, but the rules have edges.

What to discuss with a CPA. Whether Traditional or Roth fits the current year given projected future bracket. Whether a backdoor Roth is on the table for those above the phase-out. Whether the employer match at the current deferral rate captures the full match - some plans true up annually, others do not.

HSA pace

What to check. YTD HSA contributions against the 2026 limit: $4,400 self-only HDHP, $8,750 family, plus a $1,000 catch-up at 55+.

How to check it in the spreadsheet.

HSA eligibility requires HDHP enrollment for the months contributions are made. Mid-year coverage changes prorate the limit. The last-month rule allows a full-year contribution for someone HDHP-enrolled on December 1, with a testing-period requirement.

What to discuss with a CPA. Prorated limit if HDHP coverage shifted mid-year. If the HSA is used as an investment vehicle (paying current medical out of pocket, leaving HSA invested), whether medical receipts are filed for future reimbursement.

Itemize vs standard deduction projection

What to check. Whether the combined itemized deductions (state and local taxes, mortgage interest, charitable, allowable medical) will exceed the 2026 standard deduction. Per IRS Rev. Proc. 2025-32, the figures are $16,100 single, $32,200 married filing jointly, $24,150 head of household.

How to check it in the spreadsheet. A category roll-up of YTD deductible expenses, annualized:

If projected itemized lands well above standard, year-end charitable timing matters. If it lands well below, logging individual receipts is mostly wasted effort. The narrow band - within $1,000 to $2,000 of standard - is where bunching comes up. The row-by-row walkthrough in our piece on the tax deduction tracker in Google Sheets covers the schema.

What to discuss with a CPA. Bunching strategy if itemized lands close to standard. Donor-advised fund timing in a year with an income spike. SALT cap interaction in a year with unusually high state taxes.

Capital gains and losses year to date

What to check. Realized short-term and long-term gains and losses, dividends, and any wash-sale flags. The mid-year snapshot is not the final number - markets move - but the realized side is largely set.

How to check it in the spreadsheet. A few rows from the brokerage statement:

Carryover losses from prior years apply at filing. If last year left an unused capital loss carryover, line 6 of last year’s Schedule D shows the amount carried into 2026.

What to discuss with a CPA. Whether realizing gains in a known low-income year (or harvesting losses in a high-income year) fits the current bracket. Wash-sale exposure if losses were taken on positions repurchased within 30 days. Giving appreciated stock instead of cash, which substitutes for cash giving and avoids the gain.

The spreadsheet shows realized activity. It does not know your view on the market, your bracket projection, or whether a large event (home sale, business sale, inheritance) is still ahead. The data is information. The decision belongs in the conversation.

Self-employment items

What to check. For freelancers, sole proprietors, single-member LLCs, and side-hustlers: home office square footage, business mileage YTD, business expenses YTD, and estimated payments paid.

How to check it in the spreadsheet. Schedule C categories with YTD totals and line references.

Mileage especially: the IRS 2026 standard rate is 72.5 cents per mile (Notice 2026-10). A contemporaneous log (date, miles, purpose) holds up under audit; a year-end estimate does not.

What to discuss with a CPA. Whether actual-expense vehicle method beats standard mileage at current vehicle costs. Whether the QBI deduction applies (Form 8995) and the higher-income phase-out shape. Whether a Solo 401(k) or SEP IRA opens up retirement contribution room beyond the employee-side $24,500. Our self-employed deductions roundup for 2026 covers the 25 most common.

Life changes that affect tax position

What to check. Anything in the first half of the year that shifts withholding logic, filing status, or deduction picture.

The usual list:

How to check it in the spreadsheet. A small notes section at the top of the review tab: “What changed since January?” A two-line answer is enough.

What to discuss with a CPA. Each item is a question worth raising. Marriage mid-year often produces under-withholding because each W-4 assumed single brackets. Divorce inverts that. A new child changes the W-4 dependent count and may open dependent care benefits at the next open enrollment. The spreadsheet does not calculate these. It flags them.

A worked example

Tom and Priya are married filing jointly. Combined W-2 income, no side businesses. Mid-year snapshot:

The findings list is short: Tom’s 401(k) pace would miss the cap by ~$5,000 at current deferral. HSA contributions are running slightly below the family limit. Withholding is over-correcting from last year’s RSU spike, projecting a sizable refund. Three things the spreadsheet surfaced. What to do about each one is the next conversation.

The next-step list

What might change for July through December. Three to seven items, no more. Common entries from people who have run the review:

• A note to revisit the payroll 401(k) deferral percentage given the pace gap
• A reminder to revisit the W-4 if a projected refund or balance due is large and structural
• The Q3 estimated payment date (September 15) on the calendar
• A note on HSA contribution pace given the family limit
• A reference to the carryover loss for the year-end review
• A flag to pull the Roth IRA MAGI projection forward if income is near the phase-out
• A booked CPA meeting if any of the above raised questions

What does not belong: anything that depends on guessing about market returns, future income, or major life events still in the maybe column.

When the mid-year tax checkup hands off

A spreadsheet compares YTD withholding to last year’s tax. It does not know whether this year’s bracket will be higher or lower. It shows the Roth IRA contribution made so far. It does not weigh Traditional versus Roth over a thirty-year horizon. The data is what is happening. The decision - whether to adjust, when, how aggressively - belongs in the CPA conversation, ideally before October when calendars fill up.

Get the template

Three options depending on what you are starting with.

• Annual Tax Planner - The structure that makes the mid-year review take an hour. Schedule A and Schedule C categories, quarterly estimates math, safe harbor floor, deduction-vs-standard comparison. For people who want one spreadsheet for the full tax year.
• Tax Deduction Tracker - The simpler version. Log deductions by category, see the running total against the standard deduction. For people who mostly need the receipts organized.
• Tax Deduction Tracker Ultimate - Up to 150 deductions, Schedule A/C/E breakdown, quarterly summaries, and a tax-impact calculator. For higher-volume filers or anyone running multiple income streams.

All three open in Google Sheets, Excel, and LibreOffice. The data stays on your device unless you share it.

Related

• Quarterly Estimated Tax Spreadsheet: Safe Harbor Rule Explained - The full walkthrough on the safe harbor math and 2026 due dates.
• Tax Deduction Tracker in Google Sheets: Schedule A Categories, Row by Row - The deeper dive on the itemize-vs-standard question.
• Mid-Year Financial Review: A Template for Checking In - The broader six-month review that this tax checkup slots into as one of nine sections.