Several important employee benefits and payroll compliance deadlines are approaching this fall. Employers should review the requirements now and build these dates into their open enrollment, reporting and payroll calendars.
Oct. 2: ICHRA and QSEHRA Notices
Employers offering an Individual Coverage Health Reimbursement Arrangement (ICHRA)—also referred to here as a CHOICE Arrangement—or a Qualified Small Employer HRA (QSEHRA) must provide eligible employees with a written notice at least 90 days before the start of each plan year.
For arrangements operating on a calendar-year basis, the notice deadline for the 2027 plan year is Oct. 2, 2026. The notice must explain the benefit and how it may affect an employee’s eligibility for an Affordable Care Act (ACA) premium tax credit.
Oct. 15: Medicare Part D Notices
Employers sponsoring group health plans with prescription drug coverage must notify Medicare Part D-eligible individuals whether the coverage is creditable or non-creditable. For 2026, the annual notice should be distributed by Oct. 15.
The notice applies to Medicare Part D-eligible individuals enrolled in the plan’s prescription drug coverage. Many employers include it with open enrollment materials, and CMS model notices are available to help employers meet the requirement.
Oct. 15: Extended Form 5500 Deadline
For ERISA-covered employee benefit plans operating on a calendar-year basis, the extended Form 5500 filing deadline is Oct. 15, 2026. This deadline applies when the plan administrator timely requested the automatic 2½-month extension by filing IRS Form 5558 by the original due date.
Generally, Form 5500 is due by the last day of the seventh month following the end of the plan year. Small welfare benefit plans with fewer than 100 participants may be exempt when they are fully insured, unfunded, or funded through a combination of insured and unfunded benefits.
Nov. 2: Form 941 Due
Employers must file Form 941, Employer’s Quarterly Federal Tax Return, by Nov. 2, 2026, to report federal income tax, Social Security tax and Medicare tax withheld from employee wages during the third quarter of 2026—July through September.
The usual due date, Oct. 31, falls on a Saturday in 2026, moving the filing deadline to the next business day. Employers that made all required tax deposits in full and on time generally have until Nov. 10, 2026, to file.
