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CheckMark™ 1099 software

Features
Ease of use
Ease of management
Quality of support
Affordability
Market presence
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Pricing from
$239.00 one-time annual license
Free Trial
Free version unavailable
User corporate size
Small
Medium
Large
User industry
  1. Public sector and nonprofit organizations
  2. Agriculture, fishing, and forestry
  3. Construction

What is CheckMark™ 1099 software

CheckMark™ 1099 software is a U.S. information return preparation and filing tool focused on producing 1099-series forms and related transmittals. It supports businesses and accounting professionals that need to manage payee data, create recipient copies, and generate files for electronic filing. The product is oriented around annual 1099 compliance workflows rather than full income tax preparation or broader indirect tax automation.

pros

Focused 1099 compliance workflow

The product is purpose-built for preparing 1099 forms and associated year-end reporting tasks. This focus can simplify setup and day-to-day navigation compared with broader tax suites that cover many tax types. It aligns well with organizations that primarily need contractor/vendor information reporting rather than end-to-end corporate tax preparation.

Supports recurring year-end processing

1099 preparation typically involves importing or maintaining payer/payee records and producing multiple form types in a short period. A dedicated 1099 tool is generally well-suited to batch processing and repeatable annual workflows. This can reduce reliance on manual form completion when volumes increase.

Narrow scope reduces complexity

Because it targets information returns, the product avoids many features unrelated to 1099 filing (e.g., multi-entity income tax provision or broad sales tax determination). For small finance teams, a narrower feature set can reduce training time. It can also be deployed as a point solution alongside an existing accounting system.

cons

Not a full tax suite

The product focuses on 1099 information returns and does not replace corporate income tax preparation, tax provision, or broader compliance platforms. Organizations needing consolidated corporate tax workflows typically require additional software. This can lead to multiple systems for different tax obligations.

Integration depth may vary

Dedicated 1099 tools often rely on imports/exports rather than deep, prebuilt integrations across a wide range of ERPs and accounting platforms. If your AP or vendor master data lives in multiple systems, data preparation may require manual mapping and validation. This can add time during peak filing season.

Limited global coverage

1099 forms are U.S.-specific, so the product is not designed for non-U.S. information reporting regimes. Multinational organizations may need separate tooling for other jurisdictions’ withholding and reporting requirements. This limits standardization for global tax operations.

Plan & Pricing

Plan Price Key features & notes
1099 E-File Pro+ $339.00 2025 tax-year version; unlimited recipients, unlimited print & e-filings (IRIS & FIRE support); base license includes 1 company and 1 computer; Up to 120 minutes tax-year support; priority/toll-free phone support and live chat.
1099 E-File Pro $319.00 2025 tax-year version; unlimited recipients, unlimited print & e-filings (IRIS & FIRE support); base license includes 1 company and 1 computer; Up to 60 minutes tax-year support; online access to program patches.
1099 Print Pro+ $259.00 2025 tax-year version; print-focused (no e-file); unlimited recipients, unlimited print filings; base license includes 1 company and 1 computer; Up to 120 minutes tax-year support; priority/toll-free phone support and live chat.
1099 Print Pro $239.00 2025 tax-year version; print-focused (no e-file); unlimited recipients, unlimited print filings; base license includes 1 company and 1 computer; Up to 60 minutes tax-year support; online access to program patches.

Add-ons & other costs:

  • Additional Companies: $20 each
  • Additional Computer Installations: $99 each
  • Cloud Backup add-on: $69 per year
  • CD delivery (optional): $25 (digital download available)

Notes: Pricing shown is for the 2025 tax-year versions; CheckMark describes these as a flat annual/license fee rather than per-recipient charges. The vendor also provides a free demo (pre-configured sample company) for evaluation.

Seller details

CheckMark, Inc.
Private
https://www.checkmark.com/

Tools by CheckMark, Inc.

CheckMark™ 1099 software
CheckMark Payroll
CheckMark 1095 Software
Checkmark Canada Cloud Payroll Software
CheckMark MultiLedger
CheckMark Online Payroll

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