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FAQ Teachers

Basic tax FAQs

Check our FAQs for quick answers to common tax questions. Due to IRS regulations, we cannot answer specific tax questions via email or over the phone.

If after reading FAQs, you are not sure if self-service tax prep is for you, send us a short but detailed email about your situation and we will evaluate whether hiring a tax professional would be better for you and give you an honest reply via email.

For technical issues or troubleshooting, please email us as well.
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Most questions are answered in our FAQs

Yes — starting with tax year 2025, the “One Big Beautiful Bill” expanded the Educator Expense Deduction.

• It is now an itemized deduction (instead of capped at $300 above-the-line).
• Teachers can deduct actual out-of-pocket classroom expenses (books, supplies, technology, materials).

• Deduction limit: up to $2,000 (Single) or $4,000 (Married Filing Jointly if both are teachers).

• Applies only to K-12 teachers, counselors, principals, and classroom aides working at least 900 hours per year. • Keep receipts — IRS requires documentation.
Yes —
starting with tax year 2025, the “One Big Beautiful Bill” created a new federal deduction for qualified overtime/extra instructional pay.

• What qualifies: the premium portion of overtime or supplemental contracts above base salary.

• Deduction limits: up to $12,500 (Single) or $25,000 (Married Filing Jointly).

• Income limits: phases out beginning around $150,000 MAGI (higher for joint filers).

• Payroll taxes: Social Security & Medicare still apply to all wages.

• States: Each state decides whether to conform.

Yes. If you earn side income from tutoring, summer school programs, or contract teaching and get paid on a 1099-NEC, you are treated as self-employed for that income. That means you can deduct related business expenses such as mileage, supplies, books, advertising, and liability insurance on Schedule C from self-employment income not W-2 income. This is separate from your W-2 teaching income.

Not federally. Allowed in some states: AL, AR, CA, HI, MD, MN, NY, PA.

Not federally as a W-2. Some states allow it: AL, AR, CA, HI, MD, MN, NY, PA.

Yes, if between two work sites in the same day (not home-to-school commuting). Some states allow broader deductions: AL, AR, CA, HI, MD, MN, NY, PA.

• 403(b): generally age 59½ or separation from service (10% penalty applies if earlier).

• 457(b): distributions allowed immediately after separation, no 10% penalty.

No federal deduction. Most states don’t allow it either.

Not deductible federally. Some states allow it: AL, AR, CA, HI, MD, MN, NY, PA.

Not federally. Some states and school districts offer local housing assistance programs.

If line-of-duty, some or all may be tax-free federally. States differ (e.g., PA, NY have favorable treatment).

Yes, if household income is low enough. Many full-time teachers earn too much to qualify.

Yes, if for classroom use and within the Educator Expense Deduction limit. Beyond that, not deductible federally. Some states allow it.

No federal deduction, even if purchased for students. Consider using the Educator Expense Deduction if it falls under classroom supplies.

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