Archived 2025 filing edition

2025 Edition: Everything To Know About 1099 Filing This Tax Season

2025 Edition: Everything To Know About 1099 Filing This Tax Season

1099 season doesn’t have to mean chaos, spreadsheets, and last-minute corrections. This guide breaks down everything you need to stay compliant, organized, and confident heading into 2026.

Inside, you’ll find:

  • The latest IRS and state filing updates for 2025
  • Best practices for W-9 collection and TIN verification
  • How to track payment thresholds and avoid common mistakes
  • Proven strategies from teams managing thousands of 1099s

Whether you’re handling a few contractors or thousands, this guide helps you prepare early and avoid January stress.

Get the 1099 guide now

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Customers running contractor operations on Wingspan

  • Safeguard Properties
  • Global Financial Impact
  • FinFit Life
  • Teladoc Health
  • Omni Interactions
  • CRU Group
  • Pacesetter Claims
  • Octave

Published stories from finance and tax teams

Safeguard Properties

Customer case study

Safeguard Turns 250,000+ Monthly Invoices into Effortless Payouts with Wingspan

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Global Financial Impact

Customer case study

How a small team automated 28,000 invoices and weekly contractors payments

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FinFit Life

Customer case study

FinFit Life turns to Wingspan to modernize back office and provide “life-changing” contractor benefits

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