SMB Contractor 1099 Payment Threshold Tracker & W-9 Chase Automation

Stop Losing Sleep Over 1099 Deadlines

1099Sentry tracks every contractor payment across all sources, flags who's crossed the $600 threshold, and chases missing W-9s automatically — so you're never scrambling at year-end.

Live dashboard — smb-contractor-1099-payment-threshold-tr.vokrix.co

Spreadsheets that miss payments when contractors work across multiple jobs

Chasing W-9s manually via email, then forgetting who responded

Discovering a missing W-9 in January when filing is already due

How it works.

Step 1

Upload Your Payment Records

Drop in your payment files and 1099Sentry pulls every contractor payment into one place — consolidating multi-source totals automatically so nothing gets counted twice or missed.

Step 2

See Exactly Where You Stand

Your dashboard shows every contractor record color-coded by status and urgency. You can see at a glance who's approaching $600, who's crossed it, and whose W-9 is still missing.

Step 3

W-9 Requests Go Out Without You

1099Sentry sends W-9 collection requests by email, SMS, and letter — and follows up on its own until you get a response. You review exceptions. It handles the chasing.

What you get.

Nothing Falls Through the Cracks

Payment totals are tracked across every source and job. Whether a contractor worked three projects or one, their running total is always current and accurate.

W-9s Collected Before Year-End Panic

Automated outreach starts the moment a contractor approaches the threshold — not in December when it's too late to fix mistakes.

Your Dashboard Shows What Needs Attention

Color-coded severity makes it immediately clear which records are clean, which need action, and which have upcoming deadlines. No digging through rows of data.

Fewer Errors When Filing Time Comes

Clean, verified contractor records mean no last-minute corrections, no duplicate entries, and no filing on stale information that triggers IRS scrutiny.

Common questions

The W-9 you don't collect in March is the penalty you pay in February.

1099Sentry tracks every contractor payment across all sources, flags who's crossed the $600 threshold, and chases missing W-9s automatically — so you're never scrambling at year-end.

No setup required. Start with one upload.