The Roth IRA Annual Checklist: What to Review Each Year

You don’t need to watch your Roth IRA every day. A yearly check can help you confirm contribution room, review any conversion, check your investments and beneficiaries, and keep the right tax records. If you use Medicare or Marketplace health insurance, fall also brings a coverage check — with different dates for each program. Neither enrollment calendar is a Roth-conversion deadline. Keep an account-safety plan handy, too: an urgent request to move your savings deserves an independent check.

Marketplace or Medicare? Put the Right Dates on Your Calendar

Both use the words open enrollment, but they are different programs with different deadlines. Start with the coverage you have or are applying for. These are health-coverage dates, not Roth IRA contribution or conversion deadlines.

HealthCare.gov · 2027 coverage

Marketplace health insurance

For eligible people buying individual or family coverage through HealthCare.gov, including some retirees who do not yet have Medicare.

November 1, 2026

Open enrollment begins. Compare, enroll in or change a plan.

December 15, 2026

Choose a plan by this date for coverage starting January 1, 2027.

January 15, 2027

Open enrollment ends. A selection made December 16–January 15 starts February 1, 2027.

Finish the payment step: coverage also requires paying your first premium to the insurer. Follow its payment instructions and deadline.

State-run exchange? Check its own calendar rather than assuming these dates apply. Find your state’s Marketplace.

Check HealthCare.gov’s dates and coverage starts

Medicare · Fall plan changes

Medicare health and drug plans

For people already on Medicare reviewing Medicare Advantage or Part D drug coverage. Options depend on your current coverage and enrollment requirements.

From October 1, 2026

Compare available 2027 plans and read your plan’s change notice.

October 15–December 7, 2026

Join, switch or drop coverage as allowed. The plan must receive your request by December 7.

January 1, 2027

Coverage changes made in the fall window take effect.

Check your medicines, doctors, pharmacies and expected costs, not just the premium.

Not first-time signup: initial enrollment in Parts A and B follows different rules. Medigap has separate buying protections; switching back to Original Medicare does not by itself guarantee a Medigap policy.

Review Medicare’s options and plan finder · Check Medigap buying rules

A quick date check: December 10, 2026 is after Medicare’s fall window, but still before HealthCare.gov’s December 15 cutoff for January coverage. One program’s deadline does not close the other.

Outside these windows? A qualifying life event may create a special enrollment opportunity. Check the program’s rules; do not assume you must wait until next fall. Marketplace special enrollment · Medicare enrollment options.

Enrollment dates and income years are different checks

Marketplace savings: estimate your household income for the year of coverage — 2027 for a 2027 plan — not simply last year’s wages. Report changes to your application. A taxable Roth conversion in that coverage year can affect income-based savings. Use HealthCare.gov’s income rules; our early-retiree guide explains why health coverage and Roth withdrawals need separate checks.

Medicare income surcharges: Social Security generally uses income from two years earlier to determine IRMAA, the income-related addition to Part B and Part D premiums. Under that usual rule, 2027 premiums use 2025 income; a taxable conversion in 2026 usually matters for 2028 premiums. Available tax records and qualifying life-changing events can change the determination. These pairings do not predict a premium amount. See Social Security’s explanation.

Moving to Medicare? Marketplace coverage does not automatically end when Medicare starts. Check the transition instructions so you coordinate dates for the person starting Medicare without accidentally ending coverage for others.

Enrollment sources checked October 30, 2026: CMS’s October 30 Marketplace announcement, HealthCare.gov, Medicare.gov and CMS’s September 28 Medicare calendar. The Medicare income-year explanation follows SSA’s usual two-year rule. No 2027 or 2028 Medicare premium estimate is supplied.

Looking Ahead to 2027: What Is Confirmed?

You do not need to guess next year’s numbers to get organized. Different agencies announce different pieces of the retirement budget. Here is what we verified on October 27, 2026; the 2026 IRA figures elsewhere on this page still apply to 2026 contributions.

Social Security benefits

3.6% COLA

Social Security’s cost-of-living adjustment begins with benefits payable in January 2027. It is a benefit adjustment, not an increase in your IRA contribution room.

Your bank deposit can also reflect Medicare premiums and other deductions. Use your personal notice rather than simply increasing the amount currently deposited by 3.6%.

SSA’s 2027 announcement and notice information

Social Security taxable earnings

$192,300 in 2027

This is the maximum earnings amount subject to the Social Security portion of payroll tax, up from $184,500 in 2026. It is not an IRA contribution limit or a cap on all payroll taxes: Medicare has no equivalent earnings ceiling.

For an employee with wages at or above that ceiling, the 6.2% Social Security portion is $11,922.60 for 2027: $192,300 × 6.2%. The employer pays its own share. Medicare taxes are separate.

SSA’s contribution and benefit base and 2027 fact sheet

Medicare drug coverage

$2,400 in 2027

This is the annual out-of-pocket threshold for covered Part D drugs, including certain payments made on your behalf. Once reached, you pay no out-of-pocket costs for covered Part D drugs for the rest of that calendar year.

The 2027 drug-plan deductible cannot exceed $700; some plans have a lower deductible or none. This is not a cap on all health expenses. Premiums and drugs outside Part D coverage are separate.

Medicare.gov’s 2026 and 2027 drug-cost explanation

Health savings accounts

$4,500 / $9,000

The 2027 base annual HSA contribution limits are $4,500 for self-only coverage and $9,000 for family coverage. These are HSA limits, not Roth IRA limits.

Your allowable amount depends on HSA eligibility, eligible months and any catch-up. Employer contributions count toward the limit too. A published ceiling is not confirmation that you personally qualify.

IRS Revenue Procedure 2026-24, section 3 and Publication 969’s eligibility and contribution rules

Not yet verified in this checkpoint

November 5 update: The IRS has published its 2027 general tax adjustments in Revenue Procedure 2026-35. This updates the general-tax status in our October checkpoint. It does not establish the 2027 IRA contribution or workplace-plan limits; those require their own retirement-limit source check. Keep the 2026 IRA figures on this page tied to 2026 contributions.

We also have not verified a complete 2027 Part B premium and income-surcharge table in this check. The general Medicare costs page still labels its Part B figures 2026. Published Part D figures do not establish the rest of the Medicare package.

Keep the years separate: do not use a forecast as an official limit, or treat a 2027 benefit announcement as permission to replace a 2026 contribution or calculator figure.

1. Confirm You’re Eligible to Contribute

Two gates control whether you can contribute directly to a Roth IRA in a given year:

• Compensation. Wages and qualifying net self-employment income are common examples. Social Security and ordinary investment income are not IRA compensation; ordinary rental income generally is not either. Some special payments qualify. A joint-return spousal IRA can use the couple’s eligible compensation under separate limits.
• Income (MAGI) limits. MAGI means modified adjusted gross income. For 2026, direct Roth contributions phase out from $153,000 to $168,000 for single/head-of-household filers and $242,000 to $252,000 for married joint filers. At or above the upper endpoint, the direct contribution limit is zero. Married-separate filers who lived with their spouse during the year have a separate $0–$10,000 range; see the full filing-status rules.

Use the MAGI estimator as an income-based check, not a calculation of your remaining contribution room. A backdoor Roth uses a Traditional IRA contribution and a conversion: the conversion has no income ceiling, but contribution eligibility, IRA balances and tax reporting still matter. IRS Publication 590-A explains the compensation and contribution rules.

2. Check Contribution Room — and Mind the Deadline

The 2026 annual IRA ceiling is $7,500, or $8,600 if you reach 50 by December 31 ($7,500 + the $1,100 catch-up). It is one shared ceiling for regular Traditional and Roth IRA contributions, not a separate allowance for every account. Compensation and Roth income limits can reduce what you may contribute. The amounts come from IRS Notice 2025-67.

Before another deposit, account for regular contributions already made across your IRAs and any qualifying 529-to-Roth rollover using the same year’s allowance. For example, an eligible person under 50 with enough compensation, no income phaseout and no other regular IRA contributions has $5,500 of regular contribution room after a qualifying $2,000 transfer uses part of the $7,500 ceiling. The special rollover rules and the direct-Roth income test are not interchangeable.

• Use the contribution deadline, not an extended return date. It is generally the return due date, usually April 15 of the following year, without ordinary filing extensions. IRS disaster or other special deadline relief can differ.
• Tell the custodian which year it’s for. When both the current and prior year are open, select the intended year and check the confirmation. Don’t assume every custodian uses the same default.

Married with one earner? On a joint return, eligible compensation can support contributions to each spouse’s own IRA, subject to the spousal compensation calculation, each person’s annual limit and the Roth income test. See the current contribution limits.

Using a tax refund? Follow the refund-to-Roth funding walkthrough.

3. Decide Whether to Convert — and Time It

A Roth conversion moves eligible Traditional IRA money into a Roth IRA. The taxable portion counts as income; properly tracked after-tax basis is not taxed again. Conversions have no income ceiling or annual dollar cap, but transaction rules still apply. Consider:

• Estimate the full effect. A lower-income year may offer room at a lower tax rate. Only the taxable portion of a conversion adds to income and can affect income-tested benefits and premiums; do not assume the whole amount is taxable.
• Allow processing time. For a direct conversion intended for 2026, arrange completion by December 31; your custodian may have an earlier processing cutoff. The April prior-year contribution window does not let you backdate a conversion. An indirect conversion follows the separate 60-day rollover rules, including transactions spanning year-end.
• Check required distributions first. A required minimum distribution (RMD) cannot be converted. RMDs are generally due December 31, but an IRA owner’s first RMD can have an April 1 deadline the next year. Inherited accounts have different schedules.
• Check Medicare and irreversibility. The taxable portion can affect IRMAA under the usual two-year lookback. A completed conversion cannot be reversed by recharacterizing it back to Traditional.

For the transaction details, see Roth conversions and Publication 590-A’s conversion rules. Check the RMD distinctions before treating another account’s deadline as your own.

4. Check Where the Money Went

Adding money and investing it are different steps. Some accounts invest automatically; others leave deposits in cash until you act. Check your settings and statement before placing an order. Once a year, review:

• Whether cash holdings are intentional and match your needs.
• Whether the investment mix still fits your time horizon and risk tolerance.
• Fund expenses, account charges and any advisory fee. Compare the actual costs rather than assuming a universal long-term loss percentage.

5. Review Beneficiaries & Prepare a Family Handoff

Check the beneficiary designation on file and your custodian’s account agreement after a marriage, divorce, birth or death in the family. Don’t assume that changing a will also changes the IRA designation.

Most non-spouse designated beneficiaries inheriting after 2019 use the ten-year rule, but eligible designated beneficiaries have separate options, and estates or other non-designated beneficiaries follow different rules. A spouse also has special choices. Start with the inherited Roth overview, not a single deadline for every heir.

Now give someone you trust a way to find the essentials. They do not need to learn every IRA rule today. A useful handoff answers three questions: Where is it? Where are the records? Who should I call?

How to check who is named on your Roth IRA

Start with one account. Sign in directly to the firm that holds your Roth IRA, select that account and open its beneficiary settings. If you only see your profile or your trusted contact, ask the firm for the beneficiary designation it actually has on file for that IRA.

One fictional form, two separate lists

Names on the form	What the entries mean
Primary: Alex 60%, Sam 40%	These are the first people named to inherit. If both survive the owner and the designation takes effect as written, they split the account 60/40.
Contingent: Jo 100%	Jo is the backup, not a third person sharing that first split. On a form that calls on the backup only if neither primary survives, Jo receives nothing if Alex and Sam both survive.

The first list totals 100%; the backup list has its own 100%. If only Alex survives, don’t assume Sam’s 40% goes to Jo or to Sam’s children. Ask how the account agreement and any choice you marked handle that share. If no valid designation is on file, ask which default applies to this IRA.

1. Enter the whole list you intend. If anything needs changing, use the firm’s secure form. Check whether it replaces the previous list, and whether signatures or consent are needed. For a minor, trust or divorce order, check with the firm and a qualified estate attorney before relying on the result.
2. Check what the firm accepted. After processing, reopen the same account or request a written confirmation. Compare the names, primary or backup status and shares with your instructions. If a signature is pending or an old name still appears, contact the firm rather than treating a submission receipt as the final record.
3. Leave a trail, not a password. Save the dated confirmation privately. On the family sheet, note where to find it. Repeat the check for each IRA, especially after a transfer or a change in the family.

For a provider example, see Fidelity’s beneficiary walkthrough and its answers about percentages, surviving beneficiaries and confirmation. Use your own firm’s instructions for your account.

Find the account

List the firm, account type and a phone number from a statement or the firm’s official website. Label an inherited IRA separately from your own Roth IRA; a Roth 401(k) is different again.

Find the records

Point to a secure folder containing statements, beneficiary confirmations and tax history. Keep the full records there; your quick-reference sheet can simply say where they are.

Find the right person

List the custodian — the firm holding the IRA — and any tax or estate professional who knows your situation. Ask your chosen family member or friend whether they are comfortable being the first call.

Keep the history that a current balance cannot tell you

What goes in the secure records folder

Keep or confirm	Why it helps
Beneficiary confirmation	Check the primary beneficiaries and any contingent (backup) beneficiaries, their shares and the date confirmed by the firm. Recheck after moving an account. A note in this checklist does not change the designation.
First Roth IRA contribution tax year	Preserve evidence of the earliest contribution or conversion to a Roth IRA for your benefit, including at a former firm. The relevant tax year can differ from the deposit date. Opening an empty account does not start the five-tax-year qualification period.
Money in, money out	Keep contribution, conversion, rollover, transfer and withdrawal records, including Forms 5498, 1099-R and any applicable Forms 8606 with supporting tax records. One recent statement does not reconstruct the full history.
Missing pieces	Write “not yet confirmed” beside an uncertain year or amount. Ask current and former custodians what records are available; ask a tax professional to help reconcile gaps before relying on a tax-free amount.

The original owner’s five-tax-year qualification period continues after death. That is why the first contribution year matters to an heir. It is separate from the heir’s withdrawal deadline. See the inherited Roth guide for those rules. The Form 8606 recordkeeping instructions explain which supporting records to retain to verify nontaxable IRA distributions.

Give each person a clear role

• A beneficiary is named to receive assets after death, subject to the account documents and applicable law. Being named does not itself authorize them to manage your IRA while you are alive.
• A trusted contact is someone the brokerage may reach in limited circumstances. That designation alone gives no trading, withdrawal or decision-making authority.
• An agent under a financial power of attorney can have authority to act for you under that document and state law. Ask your attorney and custodian about the scope and paperwork before help is needed. A family handoff sheet grants no such authority.

The same person might hold more than one role, but each role needs its own proper arrangement. FINRA explains trusted contacts; the CFPB explains organizing records and planning for help with finances.

A simple way to start: “I’d like you to know where my Roth IRA records are and who to call if you ever need to help. Can we walk through this sheet together?”

Ask the other person to show you where they would find the folder and the firm’s phone number. Refresh the sheet each year and after an account move or family change.

If the owner dies: contact the firm promptly through a verified number and ask about its death-notification process, required documents and beneficiary next steps. Confirm the applicable withdrawal schedule before moving or taking money out. Knowing the login is not a substitute for the firm’s authorized process.

Open the printable family handoff checklist

Print the blank sheet and complete it privately. Leave passwords, security codes, Social Security numbers and full account numbers off it. Keep the completed copy secure. The printable page has no online fields or upload function.

Why add a family conversation to the yearly review?

Fidelity’s September 17, 2026 research release linked family communication with greater reported confidence in planning. Its survey covered 654 married or partnered U.S. adults age 55 or older, with at least $500,000 in net worth and an adult child; fieldwork ran November 2025–January 2026. It does not represent every family or prove conversations cause better outcomes. It is a reason to consider a conversation, not a new IRA rule.

Practical sources: FINRA on preparing account records and family contacts and IRS Publication 590-B on inherited Roth tax treatment. The FINRA article also discusses non-retirement accounts; its transfer-on-death procedures are not substituted here for IRA beneficiary rules.

6. Know Which Tax Forms to Expect

Regular Roth contributions are not deductible, and ordinary investment activity inside the account generally is not reported as your personal taxable investment income. A tax-free withdrawal is different from an unreported withdrawal: qualified Roth distributions generally still appear on your income-tax return with a taxable amount of zero. Keep records of contributions, conversions and withdrawals.

• Form 5498 — the custodian reports IRA contributions and certain other account information. Contribution information may arrive after the normal April filing deadline. Keep it; don’t attach it to the return.
• Form 8606 — used for nondeductible Traditional IRA contributions, Traditional-to-Roth conversions and certain IRA distributions, including nonqualified Roth withdrawals. A regular Roth contribution alone does not require this form.
• Form 5329 — may be needed for an excess contribution, an early-distribution additional tax or an exception. Correction timing, the withdrawal type and reporting codes matter; an early withdrawal does not always mean a penalty.
• Form 8880 — used to claim the 2026 Saver’s Credit if you meet its contribution, income, age, student and dependency conditions. It is nonrefundable, so it cannot exceed the applicable income-tax liability. The separate Saver’s Match begins with tax year 2027.
• Form 1099-R — the custodian generally reports a distribution or conversion here. It is not proof that the entire amount is taxable.

The 1099-R/5498 instructions explain custodian reporting. Use the income-tax return instructions, Form 8606 instructions and Form 5329 instructions for your filing obligations. Follow the edition for your tax year rather than assuming an earlier form’s layout is unchanged.

7. Track Your Five-Year Clocks

Five years alone does not make every withdrawal tax-free. Keep these two tests separate:

• The qualified-distribution clock: starts January 1 of the first tax year for which you contributed to any Roth IRA for your benefit, including a conversion. Tax-free earnings also require age 59½ or another qualifying condition — death, qualifying disability or a qualifying first-home distribution within its lifetime limit.
• The conversion clock: each conversion has its own period starting January 1 of its conversion tax year. Withdrawing its taxable converted portion before that period ends can trigger the 10% additional tax if you are under 59½, unless another exception applies. Once you are 59½, that additional tax no longer applies, but the separate earnings test still matters.

Regular contributions generally come out first, then conversions in order, then earnings. Review the five-year guide and Publication 590-B before a withdrawal.

8. Protect Your Account From a Fake Rescue

A caller says your savings are in danger and you must move them to a “safe account.” The emergency can be invented. This warning applies to brokerage money generally — not only Roth IRAs.

1. Pause

End the conversation. Don’t send money or install software at an unsolicited caller’s request.

2. Verify independently

Call your firm using the number on your statement or its official website. Don’t use the caller’s number or link.

3. Speak up

Talk with someone you trust before acting. Secrecy and instructions to mislead your firm are warning signs.

Check the request, not just the account name

Independent check	Scam-pressure warning
You reach the real firm through contact details you already trust.	A stranger supplies the “verification” number or link.
You can describe the request honestly to your firm and a trusted person.	You are told to keep secrets or use a cover story.
You ask the real firm to explain the destination and process.	You must buy gold or cryptocurrency to “protect” your money.

This is a safety check, not a tax ruling. It does not establish whether a proposed IRA transfer, rollover or withdrawal meets the tax rules.

One useful yearly setup: ask your brokerage firm about adding or updating a trusted contact. The firm may contact that person in limited circumstances, such as trouble reaching you or suspected financial exploitation. The designation alone does not let them trade, withdraw money or make account decisions; it is not a power of attorney.

Already sent money or shared access? Contact the real financial firm and the bank or service that handled the payment immediately. Explain what happened and ask whether the payment can be stopped or reversed; recovery is not guaranteed. Follow the FTC’s payment, password and device-access steps, and report the scam through the official reporting link there.

Safety sources checked October 10, 2026: FINRA’s September 30 transfer-pressure warning, its trusted-contact bulletin, and FTC consumer guidance. No Roth-specific fraud rate or recovery estimate is implied.

The Bottom Line

Keep a short yearly list: how much you can contribute, which tax year each transaction belongs to, where the money is invested, who is named to inherit it and which records you need. Let someone you trust know where to find the essentials. If you use Medicare or Marketplace coverage, follow the right enrollment calendar and keep the income-year check separate. Keep your firm’s verified phone number handy for a suspicious request. A complicated conversion, inheritance or filing question deserves a closer review, not a rushed checkbox.

Article updates and correction history

November 5, 2026 — Correction: Qualified wording that implied every conversion increases taxable income, and added eligible 529-to-Roth rollovers to the annual-room check. These repair incomplete explanations, not newly enacted rules. Permanent correction record.

November 5, 2026 — Source update: Noted the IRS’s newly published general tax adjustments for 2027. These do not supply the separate 2027 retirement-plan limits or Medicare premium table.

November 5, 2026 — Update: Added a two-list beneficiary example and a way to verify the names and shares an IRA provider accepted. This is a practical walkthrough, not a change in inheritance law.

October 30, 2026 — Update: Added HealthCare.gov enrollment dates for 2027 coverage alongside the Medicare fall calendar. Distinguished January and February coverage starts, state-run exchanges, premium payment and the different income years used by Marketplace savings and Medicare surcharges. This is a seasonal coverage update, not a change to Roth IRA rules.

October 27, 2026 — Update: Added Social Security’s announced 2027 taxable earnings ceiling and an employee payroll-tax illustration. Rechecked the existing HSA, Social Security benefit and Part D figures; kept unverified 2027 retirement, general-tax and full Medicare premium figures separate. This adds coverage of previously announced information, not a new IRA limit.

October 16, 2026 — Update: Added a dated 2027 source checkpoint with the announced Social Security adjustment, Medicare Part D drug-cost limits and HSA contribution limits. Kept unverified retirement, general-tax and full Medicare premium figures separate from confirmed information. The 2026 contribution guidance and earlier correction history remain unchanged.

October 15, 2026 — Update: Expanded the beneficiary review with a family handoff checklist, a printable records map and a plain-English distinction between beneficiaries, trusted contacts and financial agents. Added context from Fidelity’s family-planning research. This is practical preparation guidance, not a change to IRA law.

October 10, 2026 — Update: Added an account-safety check following FINRA’s September 30 warning about pressure to move brokerage money: independent verification, trusted contacts and first steps after a suspected scam. This is new consumer-safety coverage, not a change to IRA tax rules or a correction to earlier guidance.

October 9, 2026 — Update: Added the fall 2026 Medicare enrollment calendar for 2027 coverage, with a separate income-year explanation. This is a seasonal reminder, not a change to Roth IRA law or a new premium estimate.

October 9, 2026 — Correction: Earlier wording incorrectly said qualified Roth withdrawals do not appear on a return and described five-year periods without all their tax and penalty conditions. Corrected those summaries and qualified the compensation, shared-contribution, conversion-timing, form and inherited-account explanations. Removed unsupported investment/fee-loss generalizations. These repairs address earlier guidance, not newly enacted rules. Permanent correction record.

May 22, 2026 — Original publication.