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A Heads Up for the 2027 Filing Season

The 2026 tax year will bring significant changes to Forms 1099-MISC and 1099-NEC. While the basic process for running the O280 and V280 reports in PropertyBoss is not changing, clients should expect additional preparation and review to be required before their 1099 information is ready for filing.


These changes are being driven by new IRS reporting requirements and the transition from the IRS's former FIRE electronic filing system to the newer Information Returns Intake System (IRIS). Beginning with the 2027 filing season, IRIS will be the IRS electronic filing system for these information returns. 


Why Is the Process Changing?

There are two major reasons.


1. The IRS now requires more detailed information.

The 2026 Forms 1099-MISC and 1099-NEC contain revised reporting requirements, including separate address fields and new fields related to cash tips, Treasury Tipped Occupation Codes, and overtime compensation. The filing data itself also requires information to be more specifically identified and formatted. For example, the updated files distinguish:

  • Whether a payer or recipient is a business or individual
  • The type of taxpayer identification number, such as an EIN or SSN
  • Business names from individual first, middle, and last names
  • Country information
  • Separate address components
  • More specific formatting for taxpayer identification numbers, addresses, names, and other information

These are significant changes from some of the information PropertyBoss previously needed to produce the reports. 


2. The IRS is retiring FIRE and moving electronic filing to IRIS.

The IRS has confirmed the retirement of the Filing Information Returns Electronically system. IRIS uses different data structures and validation requirements, which means information that may have been sufficient under the previous process may now need to be identified more specifically before a filing can be completed.


What Does This Mean for PropertyBoss Users?

Your basic PropertyBoss workflow is not changing. You will still use the O280 and V280 reports as part of your 1099 process. What is changing is the amount of preparation and review surrounding those reports. For the 2026 tax year, plan for your 1099 process to include three stages:


Prepare

There will be some homework to complete before running your final reports. For example, you may need to:

  • Verify owner and vendor names and Taxpayer Identification Numbers
  • Confirm whether records represent an individual or business
  • Verify mailing addresses and country information
  • Review records for missing or incomplete tax information
  • Update Properties and Vendors located outside the United States where applicable

PropertyBoss is adding Country information where needed and plans to default applicable records to United States, so clients will primarily need to identify and update exceptions. 


Run

Run the applicable O280 and V280 reports using the normal PropertyBoss process.


Review

After running the reports, additional review will be important before considering the information final. This may include:

  • Reviewing records for missing required information
  • Confirming names and TINs are formatted correctly
  • Checking payer and recipient classifications
  • Verifying addresses and country information
  • Reviewing the appropriate 1099 amounts and reporting categories
  • Correcting incomplete or invalid information before filing
  • Checking for prohibited characters 

The updated requirements include very specific formatting and data rules, so running the report should no longer be viewed as the final step of the process.


Plan for Additional Time This Year

The most important takeaway is simple: Please allow more time for your 2026 1099 preparation than you have in previous years. There will be preparation to complete before running the reports, followed by review and possible corrections before your information can be finalized.


More Information Is Coming in November

This article is only an early look at what to expect. Additional PropertyBoss-specific instructions will be released in November 2026, including more detailed information about preparation, running the O280 and V280 reports, required review, and the updated filing process.


Releasing this information in November will give you time to begin reviewing and preparing your records before the busy January filing season begins. As in previous years, 1099 forms themselves will not be available to print until January 2027.


For now, the best thing you can do is begin reviewing your owner and vendor tax information and plan for additional time to complete your 1099 reporting this year.