Noon: Individual Tax Tips & Refund Strategies : Fall Prep for Families & Self-Employed Workers

New Haven, Connecticut : Jose’s Tax Service : August 27, 2026

Late summer is an effective planning window for individual taxpayers. Families are organizing school schedules and child-care arrangements. Self-employed workers are closing the third quarter. Both groups should use this period to verify records, review projected income, and identify tax items that may affect the 2026 federal and Connecticut returns.

The objective is not to create unnecessary expenses. The objective is to document eligible expenses, correct withholding, and prevent avoidable refund reductions or payment surprises.

Category: Individual Tax Tips & Refund Strategies | Focus: Fall preparation for families and self-employed workers

1. Complete the September 15 estimated tax review!

Self-employed individuals, independent contractors, freelancers, and other taxpayers with income not subject to adequate withholding should review their estimated tax position now.

The third federal estimated tax payment for 2026 is due September 15, 2026. The payment is generally calculated using Form 1040-ES, Estimated Tax for Individuals. Connecticut taxpayers may also need to make the corresponding state payment using Form CT-1040ES, Estimated Connecticut Income Tax Payment Coupon for Individuals, or through the Connecticut Department of Revenue Services (DRS) portal, myconneCT.

Complete these steps:

1. Reconcile January through August income. Include business receipts, contract payments, investment income, retirement distributions, and other taxable income.
2. Update deductible business expenses. Use bank statements, receipts, mileage records, software reports, and payment processor records.
3. Compare total payments with projected liability. Include federal withholding, Connecticut withholding, prior estimated payments, and applicable credits.
4. Review both federal and Connecticut obligations. A taxpayer may be current federally but underpaid to Connecticut, or the reverse.
5. Submit the September 15 payment through an official channel. Retain the confirmation and payment record.

A self-employed taxpayer may owe both income tax and self-employment tax (SE tax). Self-employment tax is generally calculated using Schedule SE (Form 1040), Self-Employment Tax.

Do not rely only on last year’s payment amount. A change in profit, filing status, dependents, or withholding may change the required payment. Underpayment can lead to penalties or a balance due when the return is filed.

Review the IRS guidance for estimated tax and the Connecticut individual income tax information before submitting a payment.

2. Track family expenses correctly!

Back-to-school spending creates substantial household activity. Most ordinary K–12 school expenses are not automatically deductible on a federal individual income tax return. School clothing, supplies, tuition, transportation, and general academic materials should not be treated as qualifying tax expenses without a specific tax rule that applies.

The more important distinction is between education costs and care costs.

Before- and after-school care

Payments for before- or after-school care may qualify for the federal Child and Dependent Care Credit when all requirements are met. The expense generally must:

• Be paid for the care of a qualifying person.
• Enable the taxpayer, and a spouse filing jointly, to work or look for work.
• Relate primarily to care and supervision rather than education.
• Be supported by provider information and payment records.

For a child, the qualifying person is generally a dependent under age 13. Different rules may apply to a spouse or dependent who is incapable of self-care.

The regular cost of attending kindergarten or a higher grade is generally an education expense, not a care expense. However, a separate supervised before- or after-school program may qualify when it meets the work-related requirements.

Organize the following information:

• Provider name, address, and taxpayer identification number.
• Invoices or statements showing dates of service.
• Amounts paid and payment dates.
• Child’s name and period of care.
• Evidence that the care supported employment or job-search activity.

The credit is generally reported on Form 2441, Child and Dependent Care Expenses. Review IRS Publication 503, Child and Dependent Care Expenses for current requirements.

Child-related credits

Review whether household changes affect eligibility for the Child Tax Credit (CTC) or the Additional Child Tax Credit (ACTC). Relevant factors may include:

• The child’s age at the end of the tax year.
• Whether the child lived with the taxpayer for more than half the year.
• Whether the child is claimed as a dependent.
• The child’s relationship to the taxpayer.
• Social Security number requirements.
• Filing status and income limitations.

The refundable portion of the Child Tax Credit may be calculated on Schedule 8812 (Form 1040), Credits for Qualifying Children and Other Dependents. Do not assume that a child qualifies solely because the child attends school or lives in the household part of the year.

Maintain custody documents, school or medical records showing residency where appropriate, and dependent identification information. These records can help resolve filing questions and reduce processing delays.

College and education credits

If a child or dependent is enrolled in college or another eligible postsecondary institution, collect tuition statements and enrollment records. The primary federal education credits are the American Opportunity Tax Credit (AOTC) and the Lifetime Learning Credit (LLC).

These credits are generally claimed using Form 8863, Education Credits (American Opportunity and Lifetime Learning Credits). The institution may issue Form 1098-T, Tuition Statement.

Do not combine K–12 expenses with postsecondary education credits. The IRS rules are specific. Consult Publication 970, Tax Benefits for Education before treating an education payment as eligible.

3. Protect the refund with a withholding check!

A refund is not created by last-minute filing activity. It reflects the relationship between tax liability, withholding, estimated payments, deductions, and credits.

Employees should use the IRS Tax Withholding Estimator before year-end. Gather:

• Recent pay stubs.
• The prior-year federal tax return.
• Expected wages for the remaining pay periods.
• Spouse’s income, if filing jointly.
• Expected self-employment or investment income.
• Anticipated credits and deductions.

If the estimator identifies a shortfall, submit an updated Form W-4, Employee’s Withholding Certificate to the employer. Additional withholding through Form W-4 may be more practical than attempting to correct the entire shortfall with a year-end payment.

Review withholding after a major life change, including:

• Marriage or divorce.
• Birth, adoption, or loss of a dependent.
• A second job.
• A significant pay increase or decrease.
• Starting or ending self-employment.
• A change from renting to owning a home.

Avoid intentionally maximizing a refund by withholding substantially more than necessary. Excessive withholding reduces current cash flow. A more precise target may improve household budgeting throughout the year.

4. Prepare self-employed records before year-end!

Self-employed taxpayers should not wait until January to reconstruct business activity. Begin a monthly close process now.

Create separate summaries for:

1. Gross receipts: invoices, deposits, payment platform reports, and Forms 1099.
2. Operating expenses: supplies, software, advertising, insurance, professional fees, and contractor payments.
3. Vehicle use: business mileage, dates, destinations, and business purpose.
4. Home office activity: qualifying area measurements and direct or allocated expenses.
5. Equipment purchases: purchase date, cost, business use, and financing records.
6. Estimated payments: federal and Connecticut confirmations.
7. Health and retirement items: applicable statements and contribution records.

Use Schedule C (Form 1040), Profit or Loss From Business, to report many sole-proprietor activities. Expenses must be ordinary, necessary, and adequately supported. Personal expenses should not be mixed with business deductions.

Year-end equipment purchases should be evaluated based on business need, cash flow, and applicable depreciation rules. Do not purchase an item solely to seek a deduction. The deduction may not equal the purchase price, and the expense may affect future depreciation or cash reserves.

5. Make practical year-end planning decisions!

Use September through December to make decisions that may affect the 2026 return.

For families

• Confirm filing status and dependent information.
• Retain child-care provider records.
• Separate tuition from before- and after-school care.
• Review college Form 1098-T information when available.
• Check whether a new job or household change requires Form W-4 updates.
• Retain charitable contribution acknowledgments.
• Review retirement plan contributions through payroll.

For self-employed individuals

• Reconcile bookkeeping through August.
• Update projected annual profit.
• Calculate expected federal and Connecticut tax.
• Schedule the September 15 estimated payments.
• Review business mileage and home-office logs.
• Confirm contractor payment records.
• Evaluate retirement plan options before applicable deadlines.
• Reserve cash for the fourth estimated payment due January 15, 2027.

Charitable contributions intended for the 2026 tax year generally must be completed by December 31, 2026. Deductibility depends on the taxpayer’s circumstances, including whether itemizing deductions is beneficial and whether the recipient is a qualified organization. Keep bank records and written acknowledgments, particularly for larger contributions.

The IRS provides additional preparation guidance through Get ready to file your taxes.

6. Use a professional review before the deadline!

A fall review can identify missing documentation while records are still available. It also allows more time to address estimated payments, withholding, dependent eligibility, and business profitability.

Jose’s Tax Service provides personalized federal and Connecticut tax preparation, year-round tax planning, bookkeeping support, and virtual or in-person appointments. New Haven-area clients and out-of-state taxpayers may request a quote or schedule a tax appointment.

Prepare the records now. Verify the September 15, 2026 estimated tax deadline. Keep family and business expenses properly classified. A structured fall review can reduce filing errors, protect eligible credits, and improve the accuracy of the final refund or balance due.

Category: Tax Planning | Tags: tax refund, personal finance, IRS tips, New Haven taxes