Ioannis Kyprianou

ACCA-qualified accountant

Ioannis Kyprianou is an ACCA-qualified accountant who writes the annuities, structured settlements, and retirement guides on Annuity Compass.

His focus is translating the parts of personal finance that are usually buried in product disclosures and tax rules into plain English: how annuity payouts are actually calculated, what a structured settlement is really worth before fees, and how retirement accounts are taxed when you draw on them.

Every guide is researched from primary sources — regulator and government material, product disclosures, and published rate filings. Figures are presented as clearly-labelled illustrative examples rather than guarantees, because rates and tax rules change. None of it is personal financial advice; it is education to help you ask better questions before you talk to a licensed professional.

Guides by Ioannis

Annuity free look period: how the cancellation window works

Life contingent structured settlement payments: what changes when payments stop at death

Roth conversion ladder: how the five-year clocks actually work

Flexible premium deferred annuity: how paying in over time changes the contract

Structured settlement agreement: the clauses that decide what you actually get

Retirement bucket strategy: how time-segmenting your savings actually works

Market value adjustment on an annuity: how an MVA works and when it costs you

Medical lien on a settlement: what gets paid back before you see the money

TSP withdrawal rules: your options after separating and the tax traps in each

Annuity in a trust: when trust ownership keeps the tax deferral and when it destroys it

How long does it take to get settlement money after you sign?

Early retirement health insurance: bridging the years before Medicare

Annuity beneficiary: what the designation actually controls

Wrongful death structured settlement: how survivors are paid

Roth 401(k) vs traditional 401(k): how to decide which bucket to fund

Inflation adjusted annuity: what rising income really costs you

Structured settlement attorney: when you need one and what they do

Survivor Benefit Plan: what SBP costs and what it actually pays

Annuity company ratings: what the letter grades actually measure

Structured settlement annuity companies: who issues the annuity and why it matters

States that don't tax retirement income: what the phrase actually covers

Annuity ladder: how staggering contracts changes what you actually own

Structured settlements and divorce: how periodic payments get classified and divided

Tax-free retirement income: what genuinely qualifies and what only looks like it

How to get out of an annuity: the five exit routes and what each costs

Settlement protection trust: what it does and when it fits

The widow's penalty: why the tax bill often rises after a spouse dies

Long-Term Care Annuity: How Hybrid Contracts Pay for Care

Are Lawsuit Settlements Taxable? How the IRS Splits a Recovery

Social Security Survivor Benefits: Who Gets What, and When

Medicaid compliant annuity: how it works and what the rules require

Medicare set aside: what an MSA is and how the money must be spent

Catch up contributions: the rules, the age 60-63 bump, and the new Roth requirement

How to buy an annuity: the steps, the checks, and the costs

Structured settlements and debt collectors: what creditors can and cannot reach

Windfall Elimination Provision: what it was and what repeal changed

Period certain annuity: how a fixed-term income payout works

What happens if the insurance company behind your structured settlement fails

Social Security spousal benefits: who qualifies and how much you get

Annuity vs IRA: How the Wrapper and the Product Differ

Structured Settlement Cash Advance: What the Word Advance Hides

Medicare IRMAA: How Income Raises Your Part B and Part D Premiums

Inherited Annuity: Payout Options and How the Tax Works

The Structured Settlement Transfer Process: How a Sale Works Step by Step

Pension Lump Sum vs Annuity: How to Weigh the Buyout Offer

Annuity vs Life Insurance: Two Contracts That Hedge Opposite Risks

Structured Settlement and Special Needs Trust: Keeping Benefits Intact

Sequence of Returns Risk: Why the Order of Returns Matters in Retirement

Registered Index-Linked Annuity (RILA): How the Buffer and Cap Actually Work

Qualified Assignment in a Structured Settlement: How IRC §130 Makes It Work

Cash Balance Plan: How This Hybrid Pension Works and Who It Suits

Fixed Annuity: How a Guaranteed-Rate Annuity Works and What It Really Costs

Attorney Fee Structured Settlement: How Lawyers Defer Contingent Fees

403(b) Plan: How the Teacher and Nonprofit Retirement Account Works

Charitable Gift Annuity: How the Part-Gift, Part-Income Arrangement Works

Structured Settlement Rated Age: Why a Shorter Life Expectancy Raises Your Payments

SIMPLE IRA: How the Small-Employer Retirement Plan Actually Works

Qualified vs Non-Qualified Annuity: How the Tax Treatment Differs

Structured Settlement Partial Sale: Selling Some Payments, Not All

457(b) Plan Explained: The Retirement Account With No Early-Withdrawal Penalty

Annuitization: How Turning an Annuity Into Lifetime Income Works

Structured Settlement Discount Rate: The Number That Sets Your Offer

HSA for Retirement: Using a Health Account as a Stealth Retirement Fund

Deferred Income Annuity: How a DIA Turns Savings Into Later Income

Structured Settlement Examples: How Payment Schedules Are Designed

Roth IRA 5-Year Rule: The Two Clocks You Have to Track

Annuity vs Pension: How the Two Retirement Incomes Really Differ

Buying a Structured Settlement: How the Purchase Side Actually Works

Substantially Equal Periodic Payments: Using 72(t) to Tap Retirement Money Early

Annuity Exclusion Ratio: How Your Annuity Income Is Taxed

Non-Qualified Structured Settlement: How It Works and When It Is Used

Net Unrealized Appreciation: The 401(k) Company Stock Tax Break

Annuity 1035 Exchange: How to Swap an Annuity Without a Tax Bill

Workers' Comp Structured Settlement: How It Works and the Medicare Trap

Mega Backdoor Roth: How High Earners Move Extra Money Into a Roth

Annuity Income Rider: How a Guaranteed Lifetime Withdrawal Benefit Works

Structured Settlement Beneficiary: What Happens to Payments After Death

The Rule of 55: Penalty-Free 401(k) Withdrawals Before 59½

Joint and Survivor Annuity: How It Protects a Surviving Spouse