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CheckMark 1099 Software

(5/5) 4 Reviews

1. Version

E-File Print
CheckMark 1099 E-File Pro+ ($239.00) CheckMark 1099 E-File Pro ($219.00)

2. Platform

Windows Mac

3. Software Delivery CD – You will receive a stand-alone CD for CheckMark 1099 Software.
Digital Download - After completing your purchase, you can download the software or update immediately from the Product Details page.

CD - $22.00 Digital Download

4. CheckMark Cloud Backup Add-On

Cloud Backup - 12 Months (+$59.00) Cloud Backup - 1 Month (+$6.00)

Note: We are currently experiencing technical difficulties processing credit card payments, Please call (800)-444-9922 8am-5pm MST to complete your purchase. Thank you for your patience.

CheckMark's 2020 1099 software processes print/E-File 1099s for MISC, INT, DIV, S, R and NEC forms. You can have unlimited companies and set up any number of recipients for each company with CheckMark 1099. With E-File Version, submit ONE e-file to the IRS with all companies included.

Attention Mac Users: All of CheckMark's programs, currently work on Mac OS 10.6 through 10.14. Our development team is working hard to complete the new 64-bit applications for Mac. We are working diligently to have it done as soon as possible. Until it's ready for release, we recommend that you don't update to Catalina on any Mac you use with our programs.

Check out more of these great features!

  • 2020 1099 Forms and e-File.
  • Allow users to "Import from prior year" any time, instead of only giving them the option once when they first run 1099.
  • Imports CheckMark Payroll employee data.
  • Utilizes the latest database technology. No database server is required.
  • Fast. Data can be imported from text files or keyed in manually.
  • Single-user capable; install locally and share data files over a local network.
  • Sensitive data is encrypted for confidentially.
  • Compatible with Macintosh or Windows computers.
  • Includes PDF User Manual and tech support for the filing year.
  • Data entry screen is similar to the 1099 Form.
  • This version allows all eFile and Print options.

CheckMark 1099 Software comes with high-quality US-based support. Read more about each plan has to offer and choose the one that fits your business needs.

CheckMark 1099 Print/E-File Pro+

Get support quickly so you can get back to business with Pro+ Support. Best for customers, who want faster and top-of-the-queue responses to their issues.

CheckMark 1099 Print/E-File Pro

Ideal for customers looking for excellent service and great value. Best for customers with basic knowledge of payroll and accounting.

CheckMark Cloud Backup Add-On

Gain complete peace of mind by backing up your tax reporting data to the cloud right from your software. For the cost of just $6 a month, it's an insurance cover for your sensitive data.


  • 100 MB Available Disk Space
  • 512 MB RAM
  • Windows Vista or higher, including Windows 10
  • Compatible printer
  • Current version Adobe Reader


  • 100 MB Available Disk Space
  • 512 MB RAM
  • Mac OS X 10.6 for Intel-based Mac or higher, including Sierra
  • Compatible printer
  • Current version Adobe Reader

Average User Rating: (5/5)

Based on 4 Reviews

Interface is similar to 1099 forms…

April 2019

I use CheckMark software for printing Form 1099s to my contractors. The software is easy to figure out when compared to my previous software, which was complicated and stressful. The interface is similar to 1099 forms that make things easier for me while filing. The pricing is affordable. I have looked at a number of different software that allows us to file 1099 online and I didn't find any that offered what CheckMark does at such a reasonable price, for unlimited contractors and unlimited filings. No hidden or surprise fees either.

Denise, Wisconsin

So much peace of mind during tax season...

February 2019

I have used CheckMark 1099 software for the past 4 years. I like the software very much and have no problem with the features, functionality and support. It's pretty easy to use with low learning curve. I am able to e-file 1099 to the IRS in a matter of minutes. It allowed me to import information through CSV files from my accounting software. For me, CheckMark has given me so much peace of mind during tax season.

Joseph, California

Intuitive tax software...

February 2019

The simplicity of CheckMark 1099 program combined with a straightforward UI makes it an easy and intuitive piece of tax software to use for 1099 filings. The E-Filing process is made easy by integrating with the IRS's FIRE electronic filing system. Importing and exporting information is also hassle free. Ultimately it does what a lot of other products on the market do, however it simply does everything better and comes at budget friendly price.

Scott, Virginia[H]

Excellent software...

February 2019

I have been using CheckMark Payroll and 1099 Print for over ten years and am so thoroughly pleased with your products and service that I will continue to purchase them. You support the products excellently and I especially like that when there is an update, you release it immediately. Thank you for your efforts.

John, Maryland