2026-2027 Compliance Calendar

Fixed-date calendar

These fall on the same date every year regardless of the client's plan year. Dates that land on a weekend move to the next business day. Category names the law each item comes from: ACA, ERISA, COBRA, HIPAA, Medicare, CAA 2021 (transparency and Rx reporting), IRC (cafeteria plan rules and excise taxes), CHIPRA, State, or Leave law. Article names become links as each article is published.

When	Requirement	Category	Companies Eligible	Performer	Article
Jan 31	Form W-2 Box 12, code DD (aggregate cost of coverage)	ACA	Employers that filed 250+ W-2s the prior year	Payroll	W-2 Reporting of Coverage Cost
Jan 31	Massachusetts Form MA 1099-HC to enrollees and XML filing on MassTaxConnect	State	Self-insured (incl. level-funded) or out-of-state-sitused plans covering MA residents; carriers handle MA-sitused insured plans	Group / AAB	State Individual-Mandate Reporting
Jan 31 and Jul 31	DOL refreshes the CHIP model notice state list	CHIPRA	Internal reminder: update the CHIP notice template in the library	AAB	Annual Notice Bundle
Feb 28	Paper Forms 1094/1095 to the IRS	ACA	Only filers with fewer than 10 information returns and an approved e-file waiver	Group / AAB / vendor	ACA Reporting (1094/1095)
Mar 1	Form M-1 to DOL	ERISA	Multiple employer welfare arrangements (some association plans, non-PEO multi-employer arrangements)	Group	Form M-1 (MEWAs)
Mar 2	Furnish 1095-C / 1095-B to employees, or post the alternative-furnishing notice and keep it up through Oct 15. NJ still requires a 1095 actually sent to each NJ resident	ACA	ALEs (1095-C); non-ALE self-funded, level-funded and ICHRA plans (1095-B)	Group / AAB / vendor; carrier for fully insured 1095-B	ACA Reporting (1094/1095)
Mar 2 (calendar-year plans)	Medicare Part D disclosure to CMS, 60 days after plan year start	Medicare	Any plan with Rx coverage that covers a Part D-eligible person	Group / AAB	Part D CMS Disclosure
Mar 31	E-file Forms 1094/1095 through IRS AIR; state copies to CA (auto-extended to May 31), NJ and RI	ACA / State	ALEs and non-ALE self-funded plans; state rows only for clients with residents in that state	Group / AAB / vendor	ACA Reporting (1094/1095); State Individual-Mandate Reporting
Apr 30	DC health-coverage filing (30 days after the IRS e-file date); San Francisco HCSO Annual Reporting Form	State	DC: self-insured plans with a DC resident, or insured ALEs with a DC resident. SF: 20+ employees worldwide with an employee working 8+ hrs/week in SF	Group / AAB	State Individual-Mandate Reporting; State Employer Mandates
Jun 1	RxDC prescription drug data submission for the prior calendar year	CAA 2021	Every group health plan; excepted benefits and account-based plans excluded	Carrier / TPA / PBM submit; the group supplies plan-level data by the vendor's spring deadline	RxDC Reporting
Jul 31	PCORI fee on Form 720, for plan years that ended in the prior calendar year	ACA	Self-funded and level-funded medical, any HRA (even with insured medical), non-excepted health FSAs. Fully insured medical: the carrier pays	Group files; AAB may prepare	PCORI Fee
Jul 31	Form 5500, or Form 5558 for a 2½-month extension (calendar-year plans)	ERISA	ERISA plans with 100+ participants at plan year start, plans funded through a trust, and MEWAs	Group as plan administrator; AAB / vendor prepares	Form 5500
Sep 30	Summary Annual Report (calendar-year plans)	ERISA	Plans that file a Form 5500 and are insured or trust-funded; unfunded self-insured plans are exempt	Group / AAB	Summary Annual Report
Oct 14	Medicare Part D creditable-coverage notice to individuals (before Oct 15)	Medicare	Any plan with Rx coverage, any size, insured or self-funded, including ICHRAs	Group distributes; AAB prepares	Part D Creditable Coverage Notice
Oct 15	Extended Form 5500 (calendar-year plans that filed a 5558); last day of the 1095 alternative-notice posting period	ERISA / ACA	As above	Group / AAB / vendor	Form 5500; ACA Reporting (1094/1095)
Nov 15 – Dec 15	Massachusetts HIRD filing on MassTaxConnect	State	6+ employees in MA in any month of the prior 12, in- or out-of-state employers, whether or not they offer coverage	Group; AAB can file	State Employer Mandates
Dec 15	Summary Annual Report for extended calendar-year filers	ERISA	As above	Group / AAB	Summary Annual Report
Dec 31	Gag clause prohibition attestation on CMS HIOS	CAA 2021	Every group health plan; excepted-benefit-only and account-based plans (HRA, health FSA) excluded	Carrier or TPA by written agreement; the plan stays responsible and keeps the confirmation	Gag Clause Attestation
Quarterly	State paid-leave premiums with UI filings; SF HCSO expenditures (30 days after quarter end); Vermont Health Care Fund Contribution (Form HC-1); Medicare Section 111 reporting	State / Medicare	Employers with employees in a mandatory paid-leave state; SF and VT as above; Section 111 by the insurer or TPA	Payroll; carrier / TPA	State Paid Leave; State Employer Mandates; Medicare Secondary Payer

Plan-year-relative deadlines

These are computed from Plan Year Start Date and Plan Year End Date on the client's Compliance Requirements record. For a calendar-year plan the fixed-date table above already shows the resulting dates.

Requirement	Category	Due	Companies Eligible	Article
Annual notice bundle (WHCRA, Newborns' Act, CHIP, special enrollment rights, Part D, patient protection, grandfathered status, wellness, No Surprises)	ACA / ERISA / HIPAA / CHIPRA / Medicare	With open-enrollment materials; CHIP no later than the first day of the plan year	Every group health plan; individual notices have their own tests in the bundle article	Annual Notice Bundle
Summary of Benefits and Coverage (SBC)	ACA	With OE materials, or 30+ days before the plan year if there is no OE; to new hires with enrollment materials; to special enrollees within 90 days; 60 days before any mid-year material change	Every group health plan, insured or self-funded. Carrier prepares for insured plans, sponsor/TPA for self-funded; the sponsor distributes either way	SBC Distribution
Form 5500	ERISA	Last day of the 7th month after plan year end; Form 5558 extends 2½ months	ERISA plans with 100+ participants at plan year start (employees + COBRA + retirees, no dependents), trust-funded plans, MEWAs	Form 5500
Summary Annual Report	ERISA	9 months after plan year end; if the 5500 was extended, 2 months after the extended due date	Plans that filed a 5500 and are insured or trust-funded	Summary Annual Report
Medicare Part D disclosure to CMS	Medicare	60 days after plan year start; 30 days after Rx coverage ends or creditable status changes	Any plan with Rx coverage covering a Part D-eligible person	Part D CMS Disclosure
ICHRA / QSEHRA notice	ACA	90+ days before the plan year; new hires no later than their first eligible day	ICHRA: any size. QSEHRA: non-ALEs with no group health plan	ICHRA / QSEHRA Notice
SPD / wrap plan document	ERISA	Within 90 days after an employee becomes a participant; 120 days after a new plan becomes subject to ERISA; restated every 5 years if amended (10 if not)	Every ERISA welfare plan, any size, any funding. Carrier certificates alone don't satisfy ERISA	SPD & Wrap Document
Nondiscrimination testing (§105(h) and §125)	IRC	Test as of the last day of the plan year; §125 document adopted before the plan year starts	§105(h): self-insured and level-funded medical, HRAs, health FSAs. §125: any plan where employees pay premiums pre-tax	Nondiscrimination Testing
ACA affordability check	ACA	Set contributions before the plan year; the affordability percentage changes each plan year	ALEs only	Employer Shared Responsibility
PCORI fee rate	ACA	Rate is set by the plan year end date; the fee itself is due the following Jul 31	See PCORI row above	PCORI Fee

Event-triggered requirements

Nothing is due until the event happens; the clock runs from the event. These are tracked as confirmed procedures on the record rather than as dated projects.

Trigger	Category	What is due, and when	Companies Eligible	Article
New hire	ACA / COBRA / Medicare	Marketplace (FLSA §18B) notice within 14 days of hire; COBRA general notice within 90 days after coverage begins; SBC with enrollment materials; Part D notice at initial enrollment; ICHRA/QSEHRA notice by the first eligible day	Marketplace notice: every FLSA-covered employer, even with no plan. COBRA: 20+ employees. Others per their own tests	Annual Notice Bundle; COBRA; SBC Distribution
COBRA qualifying event	COBRA	Employer notifies the administrator within 30 days; election notice within 14 days of that (44 days total if the employer is the administrator); 60-day election window; 45 days for the first payment	Employers with 20+ employees on more than half of business days in the prior calendar year (part-timers count as fractions)	COBRA
Loss of coverage under 20 employees, or a state that overlaps federal COBRA	State / COBRA	State continuation notice by the deadline in that state's law (AZ, MD, NJ, PA, SC, VA and others put the notice on the employer)	Fully insured policies issued in that state; self-funded ERISA plans are preempted	State Continuation (mini-COBRA)
Plan change that touches the SPD	ERISA	SMM within 210 days after the end of the plan year in which it was adopted; 60 days after adoption if it materially reduces benefits; a restated SPD substitutes	Every ERISA plan	SMM Distribution
Mid-year material modification to benefits	ACA	Updated SBC or notice 60 days before the effective date	Every group health plan	SBC Distribution
Special enrollment event (marriage, birth, loss of other coverage)	HIPAA	Employee has 30 days to enroll; 60 days for Medicaid/CHIP events	Every group health plan	Special Enrollment Process
National Medical Support Notice received	ERISA	Employer returns Part A within 20 business days (or forwards Part B); plan administrator completes Part B within 40 business days and enrolls the child if qualified	Every ERISA group health plan must have written QMCSO procedures	QMCSO Procedures
HIPAA breach discovered	HIPAA	Individuals without unreasonable delay and within 60 days; HHS within 60 days if 500+ affected (plus media), otherwise within 60 days after calendar year end	HIPAA-covered plans: all self-funded medical, HRAs, health FSAs; hands-off insured plans have limited duties	HIPAA Privacy & Security
Material change to privacy practices	HIPAA	Revised NPP within 60 days; reminder of availability at least every 3 years regardless	Non-hands-off plans	HIPAA Privacy & Security
Creditable status of Rx coverage changes	Medicare	Part D notice to individuals; CMS disclosure within 30 days	Any plan with Rx coverage	Part D Creditable Coverage Notice; Part D CMS Disclosure
IRS Letter 226-J received	ACA	Response within 90 days	ALEs	Employer Shared Responsibility
A missed notice or requirement is discovered	IRC	Human review for Form 8928 excise-tax exposure; the tax is self-reported with the employer's income tax return	Any plan with a COBRA, HIPAA/MHPAEA or HSA comparability failure	Form 8928
Written request from a participant	ERISA / ACA	SPD or plan document within 30 days ($110/day exposure); SBC within 7 business days; Part D notice on request	Every ERISA plan / group health plan	SPD & Wrap Document; SBC Distribution
FMLA or military leave	Leave law	Maintain group health coverage during FMLA on active-employee terms (50+ employees within 75 miles); USERRA continuation up to 24 months at up to 102% (all employers)	See trigger	Leave-Law Adjacency (FMLA / USERRA)

State overlays

A state rule attaches by where employees live (individual-mandate reporting), where they work (paid leave, HIRD, HCSO, Vermont and Hawaii mandates), or where the insurance policy is issued (state continuation). Self-funded ERISA plans are generally preempted from state insurance mandates, but not from state tax and reporting laws or payroll-based leave programs. Check every state on the record's States with Employees field.

Overlay	Category	States	Companies Eligible	When	Article
Individual-mandate employer reporting	State / ACA	CA, NJ, RI, MA, DC	Self-insured or level-funded plans with residents in the state (carriers handle insured plans, but NJ and MA still put verification duties on insured employers; DC also reaches insured ALEs)	MA Jan 31; NJ/RI furnish Mar 2; CA/NJ/RI file Mar 31 (CA extends to May 31); DC Apr 30	State Individual-Mandate Reporting
Mandatory paid family / medical leave or disability	State / Leave law	CA, CO, CT, DE, DC, HI, MA, ME, MN, NJ, NY, OR, RI, WA; MD contributions start Jan 1, 2027	Any employer with one or more employees working in the state; employer-share thresholds vary (CO 10+, DE 10+, ME 15+, MD 15+, MA 25+, OR 25+, WA 50+)	Register, withhold and remit quarterly, post the notice, give new-hire notice, keep health benefits during leave where required	State Paid Leave
Employer coverage mandates and assessments	State	HI (Prepaid Health Care Act), MA (HIRD, EMAC), San Francisco (HCSO), VT (Health Care Fund Contribution)	HI: any employee at 20+ hrs/week for 4 weeks. MA HIRD: 6+ MA employees. SF: 20+ employees worldwide with one working 8+ hrs/week in SF. VT: any uncovered full-time-equivalent beyond the first four	HI on eligibility; HIRD Nov 15–Dec 15; SF quarterly plus Apr 30 report; VT quarterly on Form HC-1	State Employer Mandates
State continuation (mini-COBRA)	State / COBRA	41 states plus DC have a law; none in AL, AK, HI, ID, IN, MI, MT, WA	Fully insured policies issued in the state, mostly for employers under 20 employees. CA, CT, IL, MD, MN, NC, NY, TX and WI also run alongside or extend federal COBRA	At the qualifying event. Employer notice duties in AZ, CT, MD, NJ, PA, SC, VA, TX and others; FL is carrier-issued, 18 months, premium up to 115%	State Continuation (mini-COBRA)

The full 51-jurisdiction continuation matrix lives in its own article; about half its rows are still tagged to verify against the state source before use in a client deliverable.

Year-specific figures and dates (as of September 2026)

The only section on this page that goes stale. Update it each January and whenever the IRS or CMS publishes a new figure; everything above stays true across years.

Coming season

Deadline	What	Category	Notes
Oct 14, 2026	Part D creditable-coverage notices delivered	Medicare	before the Oct 15 start of Part D enrollment
Oct 15, 2026	Extended Form 5500, calendar-year 2025 plan years	ERISA	if a 5558 was filed
Nov 15 – Dec 15, 2026	Massachusetts HIRD window	State	6+ MA employees
Dec 15, 2026	SAR for extended calendar-year filers	ERISA
Dec 31, 2026	Gag clause attestation	CAA 2021	HIOS webform
Jan 31, 2027	W-2 Box 12 DD (250+ W-2s); MA Form 1099-HC	ACA / State	payroll performs the W-2 item
Mar 1, 2027	Paper 1094/1095 (Feb 28 falls on a Sunday); Form M-1	ACA / ERISA	paper only with a waiver
Mar 2, 2027	Furnish 2026 Forms 1095-C / 1095-B, or post the alternative-furnishing notice and keep it up through Oct 15, 2027; NJ mailing; CMS Part D disclosure for calendar-year 2027 plans	ACA / Medicare	NJ residents must receive a copy
Mar 31, 2027	E-file 1094/1095; CA (auto-extension to May 31), NJ, RI state filings	ACA / State
Apr 30, 2027	DC filing; SF HCSO annual report; Q1 state paid-leave remittances	State
Jun 1, 2027	RxDC for calendar 2026	CAA 2021	confirm against current CMS instructions
Jul 31, 2027	PCORI Form 720 for plan years ending in 2026; Form 5500 / 5558 for calendar-year 2026 plans	ACA / ERISA

Indexed figures

Figure	Category	Value	Source
PCORI applicable dollar amount	ACA	$3.47 for plan years ending Oct 1, 2024 – Sep 30, 2025; $3.84 for plan years ending Oct 1, 2025 – Sep 30, 2026	IRS Notice 2025-61
ACA affordability percentage	ACA	9.96% for plan years beginning in 2026 (9.02% in 2025)	IRS Rev. Proc. 2025-25
§4980H(a) / (b) annual amounts, calendar 2026	ACA	$3,340 / $5,010 per full-time employee	IRS Rev. Proc. 2025-26
ACA reporting penalties, 2025 returns filed in 2026	ACA	$340 per return and per statement; annual cap $4,098,500	IRS 2025 Instructions for Forms 1094-C/1095-C
QSEHRA maximums, 2026	ACA	$6,450 self-only / $13,100 family	IRS Rev. Proc. 2025-32
Part D creditable-coverage simplified test	Medicare	60% or 72% allowed for calendar 2026; 72% expected to be the only simplified method from 2027	CMS Final CY 2026 Part D Redesign Program Instructions
HIPAA Notice of Privacy Practices	HIPAA	Must include 42 CFR Part 2 statements since Feb 16, 2026; HHS revised model text Feb 2026	HHS OCR
Massachusetts PFML max weekly benefit, 2026	State	$1,230.39	Mass. DFML
SF HCSO expenditure rates, 2026	State	$4.11/hr (100+ employees), $2.74/hr (20–99); exemption threshold $128,861/yr	SF OLSE

State paid-leave premium rates for 2026 are listed in the State Paid Leave article and change every January.

Requirement index

One article per row, all in the same four-part format. The subtype column is what the Project's Compliance Subtype is set to; "proposed" means the option isn't in HubSpot yet. "Flag only" items are checked on the record but don't get a Project.

Article	Category	Companies Eligible	Timing type	HubSpot subtype
ACA Reporting (1094/1095)	ACA	ALEs (50+ full-time + FTE average in the prior calendar year, controlled group combined) file 1095-C; non-ALE self-funded, level-funded and ICHRA plans file 1095-B	Fixed	ACA 1095-C Filing / Distribution; ACA 1095-B Filing / Distribution
Employer Shared Responsibility (pay or play)	ACA	ALEs only	Plan-year / event	None (feeds the 1095-C codes)
PCORI Fee	ACA	Self-funded and level-funded medical, any HRA, non-excepted health FSAs	Fixed	PCORI Fee Payment
Form 5500	ERISA	ERISA plans with 100+ participants at plan year start, trust-funded plans, MEWAs	Plan-year	Form 5500 Filing
Summary Annual Report	ERISA	Plans that file a 5500 and are insured or trust-funded	Plan-year	SAR Distribution
SPD & Wrap Document	ERISA	Every ERISA welfare plan	Plan-year	SPD / Wrap Document
SMM Distribution	ERISA	Every ERISA plan that changes a term in its SPD	Event	SMM Distribution (verify trigger)
SBC Distribution	ACA	Every group health plan	Plan-year / event	SBC Distribution
COBRA	COBRA	Employers with 20+ employees on more than half of business days in the prior calendar year	Event	COBRA Administration Confirmed
State Continuation (mini-COBRA)	State / COBRA	Fully insured policies issued in a state with a continuation law, mostly under-20 groups	Event	COBRA Administration Confirmed (state task)
HIPAA Privacy & Security	HIPAA	All self-funded medical, HRAs, health FSAs and EAPs providing medical care; hands-off insured plans have limited duties	Fixed / event	HIPAA Notice of Privacy Practices
Part D Creditable Coverage Notice	Medicare	Any plan with Rx coverage, any size	Fixed	proposed: Medicare Part D Notice (today: a task in Annual Notices Distribution)
Part D CMS Disclosure	Medicare	Any plan with Rx coverage covering a Part D-eligible person	Plan-year	proposed: Medicare Part D CMS Disclosure
Gag Clause Attestation	CAA 2021	Every group health plan except excepted-benefit-only and account-based plans	Fixed	Gag Clause Attestation
RxDC Reporting	CAA 2021	Every group health plan except excepted benefits and account-based plans	Fixed	proposed: RxDC Reporting
Transparency in Coverage	ACA / CAA 2021	Non-grandfathered group health plans	Ongoing (monthly file refresh)	proposed: Transparency in Coverage Confirmed
MHPAEA Comparative Analysis	MHPAEA / CAA 2021	Plans with mental health / substance-use benefits: all self-funded, insured large group	On request	proposed: MHPAEA Comparative Analysis
Nondiscrimination Testing	IRC	§105(h): self-insured and level-funded medical, HRAs, health FSAs. §125: any pre-tax premium arrangement	Plan-year	proposed: Nondiscrimination Testing (105(h)/125)
ICHRA / QSEHRA Notice	ACA	ICHRA any size; QSEHRA non-ALEs with no group plan	Plan-year	ICHRA/QSEHRA Notice
Annual Notice Bundle	ACA / ERISA / HIPAA / CHIPRA / Medicare	Every group health plan; per-notice tests inside the article	Plan-year (with OE)	Annual Notices Distribution
Special Enrollment Process	HIPAA	Every group health plan	Event	Special Enrollment Process Confirmed
QMCSO Procedures	ERISA	Every ERISA group health plan	Event	QMCSO Procedures Confirmed
Medicare Secondary Payer & Section 111	Medicare	20+ employees (working aged), 100+ (disability), all sizes (ESRD); Section 111 by insurer or TPA	Ongoing / quarterly	Flag only
W-2 Reporting of Coverage Cost	ACA	Employers that filed 250+ W-2s the prior year	Fixed	Flag only (payroll)
Form M-1 (MEWAs)	ERISA	Multiple employer welfare arrangements	Fixed	Flag only unless AAB places a MEWA
Form 8928	IRC	Any plan with a COBRA, HIPAA/MHPAEA or HSA comparability failure	Event	Human-review task
Leave-Law Adjacency (FMLA / USERRA)	Leave law	FMLA: 50+ employees within 75 miles. USERRA: all employers	Event	Flag only
ERISA Fidelity Bond	ERISA	Plans that hold assets in trust or hold participant contributions outside DOL timing rules	Ongoing	Flag only
State Individual-Mandate Reporting	State / ACA	Self-insured plans with residents in CA, NJ, RI, MA or DC; NJ/MA verification for insured plans; DC insured ALEs	Fixed	proposed: State Individual-Mandate Reporting
State Paid Leave	State / Leave law	Employers with employees working in a mandatory-program state	Quarterly / event	proposed: State Paid Leave (payroll performs, AAB confirms)
State Employer Mandates	State	HI employers; 6+ MA employees; 20+ employees with an SF employee; VT employers with uncovered FTEs	Fixed / quarterly