How do I file a check made payable to cash written from my business account for expenses?

If the check was a reimbursement for business-related expenses that you had paid personally, there is no tax reporting required on your individual Form 1040. I am assuming that you had receipts for all the expenses, or other contemporaneous records (travel diary, etc.) and that the business properly recorded the expenses.

Please be aware that, Miscellaneous deductions subject to the 2% limit, including unreimbursed job expenses (reported on Form 2106) have been repealed for tax years 2018 – 2025. Affected deductions include:

• Job-search expenses
• Home office†
• Union dues†
• Work-related travel, mileage, and transportation (including DOT per diem)†
• Work-related meals, entertainment, gifts, and lodging†
• Work-related tools and supplies†
• Specialized clothing or uniforms†
• Work-related education†
• Investment fees and expenses
• Safe deposit box rental fees
• Depreciation on computers used for work† or investments
• Membership in professional societies†
• Subscriptions to professional journals or trade magazines†
• Licenses and regulatory fees†
• Malpractice insurance†
• Tax-preparation fees†
• Tax advice fees†
• Educator expenses in excess of $250
• Appraisal fees for casualty losses or donations
• Hobby expenses

†Self-employed (Schedule C) filers can still deduct these business-related expenses, as they have in the past. The repeal of unreimbursed work-related deductions only affects wage- and salary-earning employees who don’t own a business or work as a contractor.