At Wingspan, we build for the real complexity of managing a contractor workforce — compliance, payments, tax, and everything in between. This quarter, we shipped updates that reduce manual work, give you more control, and make it easier for your contractors to get paid on time.

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Automated Requirement Expiration Tracking

Stop manually tracking requirement renewals. Wingspan now automatically monitors expiration dates and reminds contractors to renew before their documents expire — preventing payment delays and keeping your contractor base compliant without extra effort from your team.

Expiration dates are tracked automatically, whether pulled from uploaded documents, calculated based on your validity rules, or manually entered when needed.

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Proactive email reminders

Contractors receive automatic reminders at 30, 21, 14, 7, and 1 day before expiration, plus on expiration day, giving them enough lead time to renew before payments are affected.

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"Expiring Soon" filter

A new filter surfaces contractors with requirements expiring in the next 30 days. Visual indicators and sortable columns help you prioritize urgent renewals.-

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Expiration date overrides

xtend expiration dates when contractors need more time, such as when paperwork is in progress. All changes are logged with notes for your records.-

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Enhanced contractor portal

Contractors see clear expiration dates, countdown timers, and color-coded urgency indicators on all their requirements.

Why it matters:

Eliminates manual tracking of renewal deadlines across your contractor population

Reduces payment delays caused by lapsed compliance requirements

Gives contractors clear, timely guidance so they can act before problems arise

Maintains a complete audit trail for every expiration date change

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1099-MISC Box 6 Filing for Healthcare Clients

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Healthcare organizations can now file 1099-MISC Box 6 forms directly in Wingspan. If you pay physicians, nurses, therapists, or other medical professionals $600 or more annually, you can manage all your tax reporting in one place — using the same straightforward process as 1099-NEC filing.**Why it matters:**- Brings healthcare tax reporting into the same platform you already use for contractor management- Eliminates the need for a separate tool or manual process to handle Box 6 filings- Reduces filing errors by keeping all 1099 workflows consistent

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Cover Foreign Exchange Fees for Your International Contractors

You can now pay foreign exchange (FX) fees on behalf of your international contractors, ensuring they receive the full payment amount they're owed. When you cover these fees, Wingspan automatically tracks and bills them separately to your account, maintaining clear cost visibility.

Why it matters:

Honors contractual commitments to pay contractors net of fees without manual adjustments

Keeps FX costs visible and properly attributed in your records- Removes friction for international contractors who would otherwise see reduced payouts

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Client-Covered Instant Payout Fees

Clients can now cover instant payout fees on behalf of contractors. When activated, the contractor receives the full payout amount without any fee deduction, and the fee is billed separately to the client's account.

Why it matters:
Lets you offer fee-free instant payouts as a benefit to your contractors

Keeps fee costs clearly tracked and separated in your billing

Improves the contractor payout experience without adding reconciliation overhead