Social Security Articles

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99 Articles

Gerelyn Terzo | Jun 20, 2026 at 11:02 AM EDT

Widow’s Two-Year Tax Window on Home Sale Could Save $250,000 in Capital Gains

She is in her late 60s, a few months into widowhood, sorting through paperwork. The house she and her husband…

Gerelyn Terzo | Jun 20, 2026 at 6:02 AM EDT

His $36,000 in Rental Income Keeps 85% of His Social Security Taxable, Year After Year

The Landlord Who Thought He Built a Steady Paycheck He’s about 70, retired, and owns a rental property or two…

Gerelyn Terzo | Jun 19, 2026 at 2:02 PM EDT

This Couple’s 20-Year-Old Roth IRA Just Unlocked a $100,000 Strategy Most Retirees Miss

A couple in their early 70s is sitting on traditional IRAs they wish were smaller. Required minimum distributions (RMDs) have…

Gerelyn Terzo | Jun 19, 2026 at 10:02 AM EDT

A $60,000 Annuity Payout Pushed a Retired Couple Over the Medicare IRMAA Line Two Years Later

The Letter That Showed Up Two Years Late A married couple, both about 66 and newly on Medicare, opened their…

Gerelyn Terzo | Jun 19, 2026 at 6:02 AM EDT

He Inherited His Late Wife’s $250K Roth. But the 3-Year-Old Account Came With a Tax Catch.

A 66-year-old widower opens the brokerage statement and sees roughly $250,000 in the Roth IRA his wife opened about three…

Gerelyn Terzo | Jun 18, 2026 at 2:02 PM EDT

The $250,000 Nursing Home Bill Was Just the Start. Here’s What Happened to His Social Security Next.

A man in his early 70s watches his wife move into a nursing home after a stroke. The care runs…

Gerelyn Terzo | Jun 18, 2026 at 10:02 AM EDT

She Earns $40,000 in “Tax-Free” Muni Bond Interest. Medicare Counts Every Dollar Toward Her IRMAA.

A 68-year-old retiree built her income around municipal bonds for a simple reason: the interest is free of federal income…

Gerelyn Terzo | Jun 18, 2026 at 6:02 AM EDT

He’s Selling His Business for $900,000. Structuring It as an Installment Sale Could Spare Him a Five-Figure Medicare Surcharge.

A Big Payday With a Hidden Medicare Bill Attached Picture a 64-year-old business owner who has spent decades building something…

Maurie Backman | Jun 18, 2026 at 5:31 AM EDT

The Fed Just Held Rates Flat and May Have Set Up the Biggest Social Security Raise in Years

The Federal Reserve left interest rates unchanged on June 17 during Chairman Kevin Warsh’s first policy meeting at the…

Maurie Backman | Jun 17, 2026 at 2:15 PM EDT

Fed Holds Rates at 3.75% as Inflation Signals a Bigger 2027 Social Security COLA

There’s been a lot of pressure on recently appointed Federal Reserve Chair Kevin Warsh to cut interest rates. But…

Gerelyn Terzo | Jun 17, 2026 at 1:48 PM EDT

A Retired Teacher and Firefighter Earn $140,000 in Combined Pensions. It Put Both of Them in an IRMAA Tier.

Picture a married couple, both about 67, both newly on Medicare. She taught middle school for three decades. He spent…

Maurie Backman | Jun 17, 2026 at 1:16 PM EDT

A Bigger 2027 Social Security COLA Could Have This Dire Consequence

Even if you plan well for retirement, there’s a sneaky factor that could drive your costs up over time —…

Maurie Backman | Jun 16, 2026 at 3:24 PM EDT

The 1 Number That Might Make You Change Your Mind About When to Claim Social Security

One of the toughest financial decisions you might have to make in your lifetime is figuring out when to sign…

Gerelyn Terzo | Jun 16, 2026 at 2:02 PM EDT

Diagnosed With a Serious Illness at 62, Why He Claims His $2,300 Social Security Check Now Instead of Waiting for 70

When a Diagnosis Rewrites the Retirement Plan He spent years planning to wait until 70 for the biggest possible monthly…

Maurie Backman | Jun 16, 2026 at 11:58 AM EDT

Social Security Took in $1.45 Trillion in 2025. Here’s Why it Wasn’t Enough

Sometimes, when government agencies are slow to release information, there’s a reason for it. It’s unclear as to why the…

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Social Security Articles

All Social Security Articles

Widow’s Two-Year Tax Window on Home Sale Could Save $250,000 in Capital Gains

His $36,000 in Rental Income Keeps 85% of His Social Security Taxable, Year After Year

This Couple’s 20-Year-Old Roth IRA Just Unlocked a $100,000 Strategy Most Retirees Miss

A $60,000 Annuity Payout Pushed a Retired Couple Over the Medicare IRMAA Line Two Years Later

He Inherited His Late Wife’s $250K Roth. But the 3-Year-Old Account Came With a Tax Catch.

The $250,000 Nursing Home Bill Was Just the Start. Here’s What Happened to His Social Security Next.

She Earns $40,000 in “Tax-Free” Muni Bond Interest. Medicare Counts Every Dollar Toward Her IRMAA.

He’s Selling His Business for $900,000. Structuring It as an Installment Sale Could Spare Him a Five-Figure Medicare Surcharge.

The Fed Just Held Rates Flat and May Have Set Up the Biggest Social Security Raise in Years

Fed Holds Rates at 3.75% as Inflation Signals a Bigger 2027 Social Security COLA

A Retired Teacher and Firefighter Earn $140,000 in Combined Pensions. It Put Both of Them in an IRMAA Tier.

A Bigger 2027 Social Security COLA Could Have This Dire Consequence

The 1 Number That Might Make You Change Your Mind About When to Claim Social Security

Diagnosed With a Serious Illness at 62, Why He Claims His $2,300 Social Security Check Now Instead of Waiting for 70

Social Security Took in $1.45 Trillion in 2025. Here’s Why it Wasn’t Enough

“I Need to Pay Off the Mafia, So I’ll Go Borrow From the Cartel”: Dave Ramsey to a Caller Wanting a HELOC for Amex Debt and a New Car

The Real Cost of Retiring on Amelia Island, Florida, at 65 on $970,000 Stress Free

Here’s How You Can Retire to The Villages, Florida, at 62 on $3,000 a Month Stress Free

"I Need to Pay Off the Mafia, So I'll Go Borrow From the Cartel": Dave Ramsey to a Caller Wanting a HELOC for Amex Debt and a New Car

The Real Cost of Retiring on Amelia Island, Florida, at 65 on $970,000 Stress Free

“I Need to Pay Off the Mafia, So I’ll Go Borrow From the Cartel”: Dave Ramsey to a Caller Wanting a HELOC for Amex Debt and a New Car

The Real Cost of Retiring on Amelia Island, Florida, at 65 on $970,000 Stress Free

Social Security Articles

All Social Security Articles

Widow’s Two-Year Tax Window on Home Sale Could Save $250,000 in Capital Gains

His $36,000 in Rental Income Keeps 85% of His Social Security Taxable, Year After Year

This Couple’s 20-Year-Old Roth IRA Just Unlocked a $100,000 Strategy Most Retirees Miss

A $60,000 Annuity Payout Pushed a Retired Couple Over the Medicare IRMAA Line Two Years Later

He Inherited His Late Wife’s $250K Roth. But the 3-Year-Old Account Came With a Tax Catch.

The $250,000 Nursing Home Bill Was Just the Start. Here’s What Happened to His Social Security Next.

She Earns $40,000 in “Tax-Free” Muni Bond Interest. Medicare Counts Every Dollar Toward Her IRMAA.

He’s Selling His Business for $900,000. Structuring It as an Installment Sale Could Spare Him a Five-Figure Medicare Surcharge.

The Fed Just Held Rates Flat and May Have Set Up the Biggest Social Security Raise in Years

Fed Holds Rates at 3.75% as Inflation Signals a Bigger 2027 Social Security COLA

A Retired Teacher and Firefighter Earn $140,000 in Combined Pensions. It Put Both of Them in an IRMAA Tier.

A Bigger 2027 Social Security COLA Could Have This Dire Consequence

The 1 Number That Might Make You Change Your Mind About When to Claim Social Security

Diagnosed With a Serious Illness at 62, Why He Claims His $2,300 Social Security Check Now Instead of Waiting for 70

Social Security Took in $1.45 Trillion in 2025. Here’s Why it Wasn’t Enough

“I Need to Pay Off the Mafia, So I’ll Go Borrow From the Cartel”: Dave Ramsey to a Caller Wanting a HELOC for Amex Debt and a New Car

The Real Cost of Retiring on Amelia Island, Florida, at 65 on $970,000 Stress Free

Here’s How You Can Retire to The Villages, Florida, at 62 on $3,000 a Month Stress Free

Featured Reads

"I Need to Pay Off the Mafia, So I'll Go Borrow From the Cartel": Dave Ramsey to a Caller Wanting a HELOC for Amex Debt and a New Car

The Real Cost of Retiring on Amelia Island, Florida, at 65 on $970,000 Stress Free