1099 filing: a decision guide to automation and outsourcing
Compare 1099 software, outsourced filing, and hybrid workflows with an ownership map, cost worksheet, and practical tests for data and corrections.
Resource library
File 1099s and stay compliant
1099 season goes better when W-9s, TINs, and payment totals are clean before January. These guides cover federal and state filing, corrections, penalties, and the 2026 threshold change.
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A Step By Step Guide To Simplifying Your 1099 Filing With Wingspan
It’s time to offload your 1099 processing to Wingspan and let it own compliance on your behalf. Here's how easy it is.
How this telehealth enterprise saved 80+ hours on 1099 management with Wingspan
A fast-growing telehealth enterprise needed a better way to manage the processes behind creating and delivering thousands of 1099 forms to its growing network of mental health providers around the country. They partnered with Wingspan to make it happen.
Where this leads
Tax and 1099 compliance
Keep tax records ready from onboarding through filing.
See tax and 1099 complianceCustomer stories
See how companies in telehealth, insurance, staffing, and other industries use Wingspan to manage contractor onboarding, payments, and tax filing.
Read customer storiesBook a demo
Book a personalized Wingspan demo to see contractor onboarding, payments, and compliance workflows and discuss how they fit your team and current processes.
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All resources
1099 filing: a decision guide to automation and outsourcing
Compare 1099 software, outsourced filing, and hybrid workflows with an ownership map, cost worksheet, and practical tests for data and corrections.
A Step By Step Guide To Simplifying Your 1099 Filing With Wingspan
It’s time to offload your 1099 processing to Wingspan and let it own compliance on your behalf. Here's how easy it is.
How this telehealth enterprise saved 80+ hours on 1099 management with Wingspan
A fast-growing telehealth enterprise needed a better way to manage the processes behind creating and delivering thousands of 1099 forms to its growing network of mental health providers around the country. They partnered with Wingspan to make it happen.
1099-NEC, 1099-MISC, or 1099-K: a decision guide for businesses
Choose between 1099-NEC, 1099-MISC, and 1099-K using payment type, 2026 thresholds, reporting responsibility, and the correct filing deadlines.
1099 filing penalties: what businesses owe and how to fix a missed filing
Understand 1099 filing penalties by return due year, separate IRS and recipient obligations, and follow a practical process for missed or incorrect forms.
How to collect W-9s and verify TINs before tax season
Build a W-9 collection and TIN matching workflow with clear owners, secure updates, mismatch resolution, and records ready for 1099 review.
Demystifying the 1099 Process: How to Make This January Easy
Webinar Recap: 3 Key Challenges with 1099 Filing (and How to Solve Them)
How to Save Time, Money, & Headaches Filing 1099 Forms
Streamline Your 1099 Filing: How to Tackle Tax Season Stress-Free for Your Contractors and Business
These Are the Biggest 1099-NEC Filing Challenges (And How to Solve Them)
Hint: the solution involves automation.
How to reconcile contractor payments across multiple systems before 1099 filing
Reconcile contractor payments across platforms, AP, banks, and legacy systems with source registers, recipient mapping, and a reviewable bridge.
How To Avoid A Chaotic & Hectic 1099 Filing Season This January
1099 filing season can be incredibly stressful for finance teams. Here's everything you need to know before the filing deadline
State 1099-NEC filing requirements: a 2026 planning reference
Plan 2026 state 1099-NEC filing with a sourced 50-state and DC reference, filing-route checks, and a worksheet for unresolved requirements.
The 7 Pain Points That Make January 1099 Season a Nightmare (And How to Eliminate Them)
Stop scrambling every January: automate the manual work now and walk into tax season completely prepared
How to correct a 1099-NEC: an error-type workflow for businesses
Correct a 1099-NEC by error type and filing method. Separate rejected submissions, recipient and payer errors, duplicates, and missing originals.
1099-NEC reporting for construction and property-services networks
Connect work orders, subcontractor records, payment channels, and reporting decisions before 1099-NEC filing for property-services networks.
Save time filing 1099 forms
Hear how finance and accounting teams prepare for 1099 season, collect contractor information, and reduce the manual work behind accurate tax filings.
Contractor tax withholding: voluntary set-asides, backup withholding, and state rules
Distinguish voluntary contractor tax savings from federal backup withholding, state rules, and foreign-person payment review.
IRS B notices: how to handle CP2100 and CP2100A for contractor payments
A payer guide to identifying IRS name/TIN notices, comparing submitted and current records, and giving a qualified tax owner the evidence needed for official IRS procedures.
1099 filing season doesn’t have to suck. Here’s how to prepare for a smooth month end
I learned firsthand how stressful and complicated the 1099 filing process is when I became a freelancer at the end of 2016.