1. Guidelines for a Successful 1099 Season

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In this section:

• 1099-MISC healthcare payments: Box 6 eligibility, corporate recipients and supported scope.
• Communication Timeline & Guide: recommended communications to send to contractors and an overview of Wingspan’s outreach.
• Contractor FAQs Template: frequently asked contractor questions that you can adapt to your own help center.
• Contractor Experience Walkthrough: an end-to-end view of the contractor experience, from confirming tax information to receiving forms.
• Payer Responsibilities & Support Ownership: delineates what Wingspan support handles versus what stays with your team.
• Limitations of Wingspan Tax Filing: a checklist of scenarios we do not support.
• Other Payer FAQs: common questions from payers about the 1099 experience.
• What’s New for Tax Year 2026: highlights updates for the 2026 tax year.