Amazon Flex Taxes in Boston, Massachusetts - 2026

Updated for 2026 (Filing 2025 Taxes)

Tax Essentials for Amazon Flex Drivers in Boston, Massachusetts

Navigating the historic streets of Boston as an Amazon Flex driver offers flexibility, but also introduces unique tax considerations. Delivering packages from Back Bay to Fenway requires understanding how your earnings are taxed, both at the federal and Massachusetts state levels.

As an independent contractor for Amazon Flex, the IRS considers your earnings self-employment income. This means you are responsible for reporting your income on Schedule C (Profit or Loss from Business) with your Form 1040, and paying self-employment taxes, which cover both Social Security and Medicare. Failure to accurately report income and pay taxes can result in penalties and interest.

How Massachusetts Handles Gig Worker Taxes

As a resident of Massachusetts, you are required to file a state income tax return, even if your only income is from Amazon Flex. Massachusetts utilizes a flat income tax rate, currently at 5.0%, for the 2025 tax year. This means all taxable income is subject to the same rate. Amazon Flex earnings are considered taxable income and must be reported. The primary form for self-employed individuals to report income and calculate tax liability is Form 1040-EZ, Form 1040-A, or Form 1040, along with Schedule C and Schedule SE (Self-Employment Tax). You will also likely need to make estimated tax payments quarterly if you expect to owe $1,000 or more in taxes. Working in a densely populated city like Boston can present unique challenges, such as finding affordable parking while on duty, and these parking expenses may be deductible as a business expense (see deductions section). Demand for Flex drivers fluctuates significantly in Boston, particularly around events at Fenway Park, TD Garden, and during the college semesters, impacting potential earnings and therefore tax liability. It's crucial to maintain accurate records of all income and expenses throughout the year. For more information and resources, please visit the Massachusetts Department of Revenue: Massachusetts Department of Revenue.

Top Tax Deductions for Boston, Massachusetts Drivers

• Standard Mileage: The most common and often most beneficial deduction. The 2025 rate is 70 cents per mile. Given Boston's traffic congestion and the potential for significant mileage, this deduction can substantially reduce your tax burden.
• Tolls & Parking: Boston and its surrounding areas have tolls on major roadways. These tolls, along with parking fees incurred while actively working (e.g., during a delivery block), are deductible business expenses. Keep detailed records of all toll receipts and parking payments.
• Phone & Data Plan: If you use your personal phone and data plan for Amazon Flex deliveries (navigation, communication with Amazon, etc.), you can deduct the percentage of the bill attributable to business use.
• Vehicle-Related Costs: Expenses like car cleaning supplies, phone mounts, dash cams, and insulated hot bags used specifically for deliveries are deductible.

Key Warning: You cannot deduct both the standard mileage rate and actual car expenses like gas, oil changes, or repairs in the same year. Choose the method that yields the greater deduction.

Understanding the 15.3% Self-Employment Tax

The 15.3% self-employment tax covers both Social Security and Medicare taxes. Unlike traditional employment, Amazon Flex and other gig platforms do not withhold these taxes from your earnings. Therefore, it is your responsibility to calculate and pay this tax, typically through estimated tax payments made quarterly to the IRS. The tax applies to net earnings over $400.