Social Security Articles

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396 Articles

Gerelyn Terzo | Jul 31, 2026 at 11:04 AM EDT

Medicare Advantage Insurers Are Redrawing the Map for 2027. Members Find Out by Letter This Fall.

Millions of Medicare Advantage members will open a letter this fall that could quietly close doors they assume will always…

Gerelyn Terzo | Jul 31, 2026 at 10:03 AM EDT

Her Wisconsin Pension Rose 2.1%. The Other Part Jumped 18%. Only One Is Safe to Spend.

A retired Wisconsin teacher sees two very different numbers on her pension statement and reaches for her vacation budget. Before…

Gerelyn Terzo | Jul 31, 2026 at 7:04 AM EDT

Medicare Backdated His Coverage Six Months. His HSA Contributions Became a Tax Problem.

Working past 65 while maxing out your HSA sounds like a smart play, but a single Medicare enrollment rule can…

Gerelyn Terzo | Jul 31, 2026 at 7:02 AM EDT

He Assumed His Old Indiana Teaching Job Left Him Nothing. A State Database Found a $700-a-Month Pension Waiting.

A retired Indiana teacher spent decades assuming a brief stint in a public school left him nothing to show for…

Gerelyn Terzo | Jul 31, 2026 at 6:03 AM EDT

40% of Americans Near 60 Have No Retirement Account. For Them, Social Security Is the Whole Plan.

For millions of Americans closing in on retirement with nothing saved, Social Security becomes every financial decision rolled into one,…

Maurie Backman | Jul 30, 2026 at 8:46 PM EDT

Don’t Claim Social Security at 62 Unless You Know This Number

Claiming Social Security at 62 feels like a financial shortcut, but the lifetime math tells a very different story than…

Maurie Backman | Jul 30, 2026 at 5:30 PM EDT

Raising Taxes on Higher Earners to Save Social Security Has (Shocking) Bipartisan Support

Social Security is running out of time, and a surprising political alliance may have found a way to fix it…

Gerelyn Terzo | Jul 30, 2026 at 3:02 PM EDT

He Broke Even at the Casino Last Year. Medicare Counted Every Jackpot and Ignored Every Loss.

A retired gambler who lost money overall still watched his Medicare premiums spike by nearly $3,000 two years later, and…

Gerelyn Terzo | Jul 30, 2026 at 2:02 PM EDT

They Downsized in Michigan to Stretch Their Social Security. The New Tax Bill Ate the Whole COLA Raise.

Selling a larger Michigan home to cut costs in retirement sounds straightforward until the new property tax bill arrives and…

Maurie Backman | Jul 30, 2026 at 1:29 PM EDT

Millionaires Stop Paying Into Social Security by Early March. Here’s the Fight Over Changing That

Social Security faces a funding crisis that could slash benefits within years, and the debate over who should pay more…

Gerelyn Terzo | Jul 30, 2026 at 11:02 AM EDT

She Converted $200,000 to a Roth at 68. The Five-Year Rule Just Started Her Clock.

Converting a traditional IRA to a Roth at 68 sounds like a clean escape from future taxes, but one overlooked…

Gerelyn Terzo | Jul 30, 2026 at 10:03 AM EDT

His Income Topped Pennsylvania’s $48,110 Rebate Limit. He Still Qualified.

Frank tallied his Social Security and pension every spring, decided he earned too much for Pennsylvania's property tax rebate, and…

Gerelyn Terzo | Jul 30, 2026 at 8:03 AM EDT

Medicare Expands Price Negotiation to Injectable Drugs for the First Time. Your Coinsurance Could Drop by 2028

Medicare's new drug negotiation list just crossed into territory it has never touched before, and if a nurse has ever…

Gerelyn Terzo | Jul 30, 2026 at 7:04 AM EDT

Two Millennials, Same Age, Opposite Retirements. The 2033 Social Security Cliff Hits Them Very Differently.

Two millennials, same birthday, same projected Social Security cut. But when the trust fund runs dry, one of them barely…

Gerelyn Terzo | Jul 30, 2026 at 6:02 AM EDT

His 401(k) Hit a Record High on AI Stocks. Why His Social Security Check Matters More Than Ever.

A record 401(k) balance feels like the best possible way to enter retirement, but for a new retiree sitting on…

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Social Security Articles

All Social Security Articles

Medicare Advantage Insurers Are Redrawing the Map for 2027. Members Find Out by Letter This Fall.

Her Wisconsin Pension Rose 2.1%. The Other Part Jumped 18%. Only One Is Safe to Spend.

Medicare Backdated His Coverage Six Months. His HSA Contributions Became a Tax Problem.

He Assumed His Old Indiana Teaching Job Left Him Nothing. A State Database Found a $700-a-Month Pension Waiting.

40% of Americans Near 60 Have No Retirement Account. For Them, Social Security Is the Whole Plan.

Don’t Claim Social Security at 62 Unless You Know This Number

Raising Taxes on Higher Earners to Save Social Security Has (Shocking) Bipartisan Support

He Broke Even at the Casino Last Year. Medicare Counted Every Jackpot and Ignored Every Loss.

They Downsized in Michigan to Stretch Their Social Security. The New Tax Bill Ate the Whole COLA Raise.

Millionaires Stop Paying Into Social Security by Early March. Here’s the Fight Over Changing That

She Converted $200,000 to a Roth at 68. The Five-Year Rule Just Started Her Clock.

His Income Topped Pennsylvania’s $48,110 Rebate Limit. He Still Qualified.

Medicare Expands Price Negotiation to Injectable Drugs for the First Time. Your Coinsurance Could Drop by 2028

Two Millennials, Same Age, Opposite Retirements. The 2033 Social Security Cliff Hits Them Very Differently.

His 401(k) Hit a Record High on AI Stocks. Why His Social Security Check Matters More Than Ever.

Why Your Ex-Spouse Could Inherit Your $600,000 401(k) Even After Remarriage

Gold Went Flat in 2026. This Award-Winning Fund Still Milks 13% Income Out of It

Married 9 Years? One More Anniversary Changes What Social Security Owes You Forever

Why Your Ex-Spouse Could Inherit Your $600,000 401(k) Even After Remarriage

Married 9 Years? One More Anniversary Changes What Social Security Owes You Forever

Why Your Ex-Spouse Could Inherit Your $600,000 401(k) Even After Remarriage

Gold Went Flat in 2026. This Award-Winning Fund Still Milks 13% Income Out of It

Social Security Articles

All Social Security Articles

Medicare Advantage Insurers Are Redrawing the Map for 2027. Members Find Out by Letter This Fall.

Her Wisconsin Pension Rose 2.1%. The Other Part Jumped 18%. Only One Is Safe to Spend.

Medicare Backdated His Coverage Six Months. His HSA Contributions Became a Tax Problem.

He Assumed His Old Indiana Teaching Job Left Him Nothing. A State Database Found a $700-a-Month Pension Waiting.

40% of Americans Near 60 Have No Retirement Account. For Them, Social Security Is the Whole Plan.

Don’t Claim Social Security at 62 Unless You Know This Number

Raising Taxes on Higher Earners to Save Social Security Has (Shocking) Bipartisan Support

He Broke Even at the Casino Last Year. Medicare Counted Every Jackpot and Ignored Every Loss.

They Downsized in Michigan to Stretch Their Social Security. The New Tax Bill Ate the Whole COLA Raise.

Millionaires Stop Paying Into Social Security by Early March. Here’s the Fight Over Changing That

She Converted $200,000 to a Roth at 68. The Five-Year Rule Just Started Her Clock.

His Income Topped Pennsylvania’s $48,110 Rebate Limit. He Still Qualified.

Medicare Expands Price Negotiation to Injectable Drugs for the First Time. Your Coinsurance Could Drop by 2028

Two Millennials, Same Age, Opposite Retirements. The 2033 Social Security Cliff Hits Them Very Differently.

His 401(k) Hit a Record High on AI Stocks. Why His Social Security Check Matters More Than Ever.

Why Your Ex-Spouse Could Inherit Your $600,000 401(k) Even After Remarriage

Gold Went Flat in 2026. This Award-Winning Fund Still Milks 13% Income Out of It

Married 9 Years? One More Anniversary Changes What Social Security Owes You Forever

Featured Reads

Why Your Ex-Spouse Could Inherit Your $600,000 401(k) Even After Remarriage

Married 9 Years? One More Anniversary Changes What Social Security Owes You Forever