October 2025 Sun Mon Tue Wed Thu Fri Sat Apply to CMS for the Retiree Drug reimbursement arrangements (QSEHRAs) must provide a A Subsidy (Calendar-year Plans Only) notice to eligible employees regarding the QSEHRA’s The retiree drug subsidy (RDS) is available to certain coverage. This notice must be provided at least 90 days employers who sponsor group health plans covering before the beginning of each plan year. For QSEHRAs that retirees who are entitled to enroll in Medicare Part D but operate on a calendar-year basis, this notice must be elect not to do so. To participate in the RDS program, provided by Oct. 3, 2025, for the upcoming 2026 plan year. eligible employers must submit an application to CMS Provide Medicare Part D Notices to before the beginning of the plan year by a date specified D Plan Participants by CMS (usually about 90 days before the beginning of the Notify Medicare Part D eligible individuals by Oct. 14, plan year). The approximate deadline is Oct. 2, 2025, for 2025, whether the health plan’s prescription drug plan years beginning on Jan. 1, 2026. This deadline may be coverage is creditable or non-creditable. extended by 30 days if CMS grants an extension. Provide ICHRA Notice for 2026 Plan File Form 5500 for the 2024 Plan B Year E Year if Form 5500 Deadline Was Employers that offer individual coverage health Extended reimbursement arrangements (ICHRAs) must provide a File Form 5500 with the DOL by Oct. 15, 2025, if you have notice to eligible employees regarding the ICHRA’s a calendar-year plan and applied for the automatic 2.5- coverage. This notice must be provided at least 90 days month filing extension. before the beginning of each plan year. For ICHRAs that File Form 941, Employer’s Quarterly operate on a calendar-year basis, this notice must be F Federal Tax Return provided by Oct. 3, 2025, for the upcoming 2026 plan year. A model notice is available for employers to use. File Form 941 with the IRS by Oct. 31, 2025, to report the federal income tax, Social Security tax and Medicare tax C Provide QSEHRA Notice for the 2026 you withheld from your employees’ pay during the third Plan Year (Calendar-year quarter of 2025 (July, August and September). If your Plans Only) company was timely in depositing all taxes when they were Employers that offer qualified small employer health due, the filing deadline is extended to Nov. 10, 2025.