Case File 017: The Disappearing Contractor Payments — When 1099s Miss the Mark

Filed under: Vendor Misclassification & Tax-Time Trouble

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The client was sure they’d paid their contractors. The bank statements agreed. But when 1099s were generated? Crickets. Detective Debit raised an eyebrow. “Let’s check the setup.”

A tax form on a wooden desk with a large bold number 1099 and three colored question marks over it.
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Detective Debit investigates bookkeeping mysteries and uncovers hidden financial clues. She solves cases involving vague accounts, misclassified expenses, and audit risks.

Turns out, the vendors were paid—but not coded correctly. Some were marked as “Other,” others weren’t flagged for 1099s at all. And a few were paid via platforms that don’t require reporting—but no one remembered which..

A pink note listing clues related to business issues: missing 1099 match, vendor profile gaps, wrong expense codes, and reporting confusion.

The Clues

  • Contractors paid via check or bank transfer, but not showing up on 1099 reports

  • Vendor profiles missing tax ID info or 1099 eligibility

  • Payments coded to expense accounts that don’t trigger reporting

  • Confusion over what counts as a reportable payment

 The Twist

QuickBooks only includes vendors in 1099s if they’re flagged and paid through eligible methods. If the setup’s wrong—or the payments are miscategorized—they vanish from the report. And come tax time, that’s a problem for everyone.

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Detective Debit’s fix?

Audit vendor profiles, verify payment methods, and run a 1099 preview before January.

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The Takeaway Don’t wait until tax season to check your 1099s. Review vendor settings quarterly, confirm tax ID info, and make sure payments are coded to the right accounts. A little prep now saves a lot of scrambling later.

A magnifying glass hovering over a contractor's 1099 form representing tax or financial analysis.

Need Backup? If your 1099s are missing names you know you paid, I can help you trace the trail, fix the flags, and make sure your records are IRS-ready—without the panic.

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Case File 018 — The Case of the Overstated Profit

The reports looked great—too great. Detective Debit noticed the Cost of Goods Sold was suspiciously low. A deeper dive revealed missing expenses, miscategorized purchases, and a profit margin that was more fiction than fact.