Your Mid-Year Tax Check-In | 3 Moves Before June 15

Your Mid-Year Tax Check-In | 3 Moves Before June 15
A practical guide from Avondale Advisory PLLC — tax planning, CFO, and accounting for growth-minded business owners.
Estimated Tax Season
June 15 Deadline
Why June 15 Matters
The IRS expects taxes to be paid as you earn — not just at filing time. June 15 is the Q2 estimated tax deadline, and missing it means owing a penalty, even if you pay everything in full by April.
Pay-As-You-Go System
The U.S. tax system requires quarterly payments throughout the year for self-employed individuals, business owners, and high earners without sufficient withholding.
Miss It, Pay a Penalty
The underpayment penalty is calculated per quarter — so missing Q2 costs you even if Q3 and Q4 are paid on time. There's no catch-up credit for late quarters.
Key Dates to Know
       Q1: April 15
       Q2: June 15 ← You are here
       Q3: September 15
       Q4: January 15     
Move 1 : Pick the Cheaper Safe Harbor
The IRS gives you two ways to avoid the underpayment penalty. You don't have to guess your exact tax bill — you just have to hit one of these targets. Pay the lower one. Avoid the penalty. Keep your cash.
Option A
90% of your current year's estimated tax liability
Best when your income is down from last year — you pay less overall.
Option B
100% of last year's tax
(or 110% if your AGI exceeded $150K)
Best when your income is up — lock in last year's lower number.
The Strategy: Compare both options each quarter and pay whichever is smaller. This is a legal, IRS-approved method to minimize cash outflow while staying penalty-free. 
Move 2 : Re-Project Your Income Mid-Year
Q2 is the inflection point where actuals start replacing assumptions. Your January estimate was based on a plan. Now you have real numbers — use them.
1
Pull your year-to-date revenue and expenses
Compare against your original projection. Are you tracking ahead or behind?
2
Flag a 20%+ variance as a trigger
If income is up or down more than 20% from your plan, your estimated payments need a refresh — in either direction.
3
Recalculate Q3 and Q4 payments now
Adjust the remaining two quarters to reflect your updated projection. Don't wait until September.
Why This Matters
       Overpaying ties up cash unnecessarily. Underpaying triggers penalties. A mid-year re-projection keeps you in the optimal zone — penalty-free and cash-efficient.     
Common Triggers for a Re-Projection:
       • New client or contract win
       • Lost a major account
       • Sold a business asset
       • Unexpected bonus or distribution     
Move 3 : Note the Q4 Safety Valve
Fell behind on estimated payments? There's a powerful year-end tool most business owners don't know about: increasing W-2 withholding in December.
Increase W-2 Withholding in December
If you or your spouse receive a W-2 salary, ask your payroll provider to withhold a large lump sum in December — even a one-time adjustment works.
The IRS Treats It as Paid Evenly All Year
Unlike estimated payments (which are date-stamped), W-2 withholding is treated by the IRS as if it were paid equally across all four quarters — regardless of when it was actually withheld.
This "Cures" All Four Quarters
A December withholding increase can retroactively satisfy underpayments from Q1 through Q4, eliminating penalties for the entire year.
The Bottom Line
This strategy is especially powerful for business owners who also draw a W-2 salary from their S-Corp or have a spouse with W-2 income. It's a legal, IRS-recognized method to correct underpayments at year-end — no penalties, no questions.
Act in December — not January. Withholding must occur in the tax year to count.     
Ready to Run the Numbers?
These three moves — choosing the right safe harbor, re-projecting mid-year, and knowing your Q4 safety valve — can save you thousands in unnecessary penalties and keep your cash working for your business.
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Tax planning, CFO, and accounting for growth-minded business owners.
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