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Tax & Bookkeeping
W-2 vs 1099 for route staff
Classify workers correctly.
Updated Feb 9, 2026
Overview
Payroll and contractor rules affect withholding, reporting, and compliance. Classify workers correctly.
Diagnostics
- Confirm worker classification (W-2 vs 1099).
- Review payroll tax filings.
- Check if state unemployment applies.
Resolution steps
- Use payroll software for accuracy.
- Issue 1099s on time.
- Maintain employee time tracking.
Preventive maintenance
- Document roles and responsibilities.
- Keep signed W-9s on file.
- Review payroll filings quarterly.
When to contact support
- Misclassified workers.
- Late payroll filings.
- Not sure about state requirements.
See packages and pricing at /tax-services. Talk to a specialist at /contact.
Expanded guidance
- Confirm all steps are documented so the next technician can reproduce the results.
- Capture before/after metrics (errors cleared, sales restored, or uptime improved).
- Review machine, reader, or route settings to ensure they match location standards.
Common pitfalls
- Skipping a controlled test leads to false positives.
- Updating hardware without documenting configuration changes.
- Forgetting to verify payout, refund, or reconciliation data after changes.
Next-step checklist
- Run a final test with known-good inputs.
- Log the outcome with date, time, and device identifiers.
- Schedule a follow-up check if the location has high traffic or seasonal demand.
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Additional details
Operational notes
- Document changes with time, machine ID, and location name.
- Verify settings, pricing, and service modes after each fix.
- Capture before/after results to confirm resolution.
Field checklist
- Test with known-good inputs and controlled conditions.
- Validate telemetry, alerts, and payment logs where applicable.
- Confirm location expectations and update the site contact.
Common root causes
- Configuration drift after firmware or component swaps.
- Inconsistent power or network conditions at the location.
- Gaps in preventive maintenance routines.
Next steps
- Monitor for 7 days and note any repeat errors.
- Schedule follow-up if the site is high-traffic.
- Escalate with full logs and photos if issues repeat.
Tax & bookkeeping details
Reporting cadence
- Reconcile bank feeds weekly and close monthly.
- Compare cash vs cashless performance by route.
Documentation
- Store receipts with clear category tags and dates.
payroll1099compliancew2