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182 Articles

Gerelyn Terzo | Jun 10, 2026 at 2:00 PM EDT

The Roth Conversion Window Before Social Security: A Retiree’s Tax Strategy Worth $66,000

The Invisible Stretch Between Retirement and Benefits A 66-year-old retiree stops working, has a sizable traditional IRA, and delays Social…

Christy Bieber | Jun 10, 2026 at 1:59 PM EDT

Nearly 20% of Your Tax Dollars Now Pay Interest On Your Debt. Here’s the 2032 ‘Doomsday Scenario’ That Could Cripple Social Security

In fiscal year 2026, the Congressional Budget Office estimates that the federal budget deficit will total $1.9 trillion, which is…

Gerelyn Terzo | Jun 10, 2026 at 10:00 AM EDT

The $30,000 Stock Sale That Subtly Pulled a 68-Year-Old’s Social Security Into the Tax Torpedo

The sale that looked harmless Picture a 68-year-old single retiree living mostly on Social Security with a modest taxable brokerage…

Gerelyn Terzo | Jun 10, 2026 at 6:10 AM EDT

Why $34,000 Is the Social Security Tax Threshold Most Retirees Never See Coming

Ask 10 retirees whether Social Security gets taxed and you get 10 different answers. Some swear it is never taxed.…

David Beren | Jun 9, 2026 at 4:03 PM EDT

Fidelity’s 2026 Study: 76% of Boomers Are Counting on Social Security While Younger Generations Lean on Workplace Plans

Fidelity’s 2026 retirement study draws a clear line between generations based on where they expect their retirement income to come…

Gerelyn Terzo | Jun 9, 2026 at 2:00 PM EDT

We’ve Been Married 40 Years. Why Is My Wife’s Social Security Only $1,000 a Month When Mine Is $3,200?

Four decades of marriage, both retired, and the monthly Social Security deposits look wildly mismatched. His check lands at about…

Gerelyn Terzo | Jun 9, 2026 at 1:29 PM EDT

My Ex-Husband Died and I Didn’t Even Know. Can I Still Claim Social Security Survivor Benefits on His Record?

A woman in her sixties has not spoken to her ex-husband in 20 or 30 years. He remarried, moved away,…

Maurie Backman | Jun 9, 2026 at 1:06 PM EDT

Social Security Becomes a Flashpoint as Lawmakers Clash Over Funding

Social Security is facing some serious problems in the coming years. And policymakers can no longer afford to sit on…

Gerelyn Terzo | Jun 9, 2026 at 11:58 AM EDT

I’m 65 and Widowed. Switching My Social Security Out of Fear Could Shrink My Check 8% a Year for Life

A 65-year-old widow lost her husband in 2014. Health problems pushed her to claim a reduced survivor benefit at 60,…

Maurie Backman | Jun 9, 2026 at 6:18 AM EDT

Social Security’s $68 Billion Giveaway Just Ran into a Brick Wall

If Social Security is a big source of retirement income for you, you may be hoping for a larger…

Gerelyn Terzo | Jun 8, 2026 at 4:19 PM EDT

The RMD Trap: How a Single $95,000 Withdrawal Blindsided a 73-Year-Old’s Medicare Costs

Why a Routine Withdrawal Casts a Long Shadow Tom is 73, single, on Medicare, and lives in the kind of…

Gerelyn Terzo | Jun 8, 2026 at 3:45 PM EDT

The Roth Conversion That Added $999.60 to a Retiree’s Medicare Bill…Two Years Later

Mary did everything the retirement books told her to do. At 68, already on Medicare and watching her traditional IRA…

Gerelyn Terzo | Jun 8, 2026 at 11:26 AM EDT

The Medicare Lookback Clause That Turned a $552,000 Real Estate Gain Into a $5,880 Bill

A 67-year-old retiree closes on the house she bought in 1998, deposits a life-changing check, and feels like she finally…

Gerelyn Terzo | Jun 7, 2026 at 5:00 PM EDT

The Divorced Spouse Strategy That Adds $14,400 a Year for a 66-Year-Old Whose Ex Is Still Alive

A 66-year-old woman was married for 14 years, divorced nearly two decades ago, and never remarried. Her career after the…

Carl Sullivan | Jun 7, 2026 at 1:12 PM EDT

Retired Postal Worker With $720,000 Discovers His Pension Just Triggered an IRMAA Surprise

The Civil Service Retirement System (CSRS) pension provides a reliable paycheck every month. So a retired United States Postal Service…

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Social Security Articles

All Social Security Articles

The Roth Conversion Window Before Social Security: A Retiree’s Tax Strategy Worth $66,000

Nearly 20% of Your Tax Dollars Now Pay Interest On Your Debt. Here’s the 2032 ‘Doomsday Scenario’ That Could Cripple Social Security

The $30,000 Stock Sale That Subtly Pulled a 68-Year-Old’s Social Security Into the Tax Torpedo

Why $34,000 Is the Social Security Tax Threshold Most Retirees Never See Coming

Fidelity’s 2026 Study: 76% of Boomers Are Counting on Social Security While Younger Generations Lean on Workplace Plans

We’ve Been Married 40 Years. Why Is My Wife’s Social Security Only $1,000 a Month When Mine Is $3,200?

My Ex-Husband Died and I Didn’t Even Know. Can I Still Claim Social Security Survivor Benefits on His Record?

Social Security Becomes a Flashpoint as Lawmakers Clash Over Funding

I’m 65 and Widowed. Switching My Social Security Out of Fear Could Shrink My Check 8% a Year for Life

Social Security’s $68 Billion Giveaway Just Ran into a Brick Wall

The RMD Trap: How a Single $95,000 Withdrawal Blindsided a 73-Year-Old’s Medicare Costs

The Roth Conversion That Added $999.60 to a Retiree’s Medicare Bill…Two Years Later

The Medicare Lookback Clause That Turned a $552,000 Real Estate Gain Into a $5,880 Bill

The Divorced Spouse Strategy That Adds $14,400 a Year for a 66-Year-Old Whose Ex Is Still Alive

Retired Postal Worker With $720,000 Discovers His Pension Just Triggered an IRMAA Surprise

Stock Market Live July 14, 2026: S&P 500 (SPY) Regaining Lost Ground on Inflation Report

Live Nasdaq Composite: Tech Stocks Rise in Relief, Treasury Yields Fall as Cooler Inflation Gives Markets a Tailwind

A Dividend Portfolio That Can Cover the Cost of Living in San Francisco

AI Is Much More Dangerous Than You Think

Americans Gave a Record $617 Billion Last Year. The Retirees Who Wrote Checks Instead of Using This IRA Move Overpaid the IRS.

A Dividend Portfolio That Can Cover the Cost of Living in San Francisco

Americans Gave a Record $617 Billion Last Year. The Retirees Who Wrote Checks Instead of Using This IRA Move Overpaid the IRS.

A Dividend Portfolio That Can Cover the Cost of Living in San Francisco

AI Is Much More Dangerous Than You Think

Social Security Articles

All Social Security Articles

The Roth Conversion Window Before Social Security: A Retiree’s Tax Strategy Worth $66,000

Nearly 20% of Your Tax Dollars Now Pay Interest On Your Debt. Here’s the 2032 ‘Doomsday Scenario’ That Could Cripple Social Security

The $30,000 Stock Sale That Subtly Pulled a 68-Year-Old’s Social Security Into the Tax Torpedo

Why $34,000 Is the Social Security Tax Threshold Most Retirees Never See Coming

Fidelity’s 2026 Study: 76% of Boomers Are Counting on Social Security While Younger Generations Lean on Workplace Plans

We’ve Been Married 40 Years. Why Is My Wife’s Social Security Only $1,000 a Month When Mine Is $3,200?

My Ex-Husband Died and I Didn’t Even Know. Can I Still Claim Social Security Survivor Benefits on His Record?

Social Security Becomes a Flashpoint as Lawmakers Clash Over Funding

I’m 65 and Widowed. Switching My Social Security Out of Fear Could Shrink My Check 8% a Year for Life

Social Security’s $68 Billion Giveaway Just Ran into a Brick Wall

The RMD Trap: How a Single $95,000 Withdrawal Blindsided a 73-Year-Old’s Medicare Costs

The Roth Conversion That Added $999.60 to a Retiree’s Medicare Bill…Two Years Later

The Medicare Lookback Clause That Turned a $552,000 Real Estate Gain Into a $5,880 Bill

The Divorced Spouse Strategy That Adds $14,400 a Year for a 66-Year-Old Whose Ex Is Still Alive

Retired Postal Worker With $720,000 Discovers His Pension Just Triggered an IRMAA Surprise

Stock Market Live July 14, 2026: S&P 500 (SPY) Regaining Lost Ground on Inflation Report

Live Nasdaq Composite: Tech Stocks Rise in Relief, Treasury Yields Fall as Cooler Inflation Gives Markets a Tailwind

A Dividend Portfolio That Can Cover the Cost of Living in San Francisco

AI Is Much More Dangerous Than You Think

Americans Gave a Record $617 Billion Last Year. The Retirees Who Wrote Checks Instead of Using This IRA Move Overpaid the IRS.

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A Dividend Portfolio That Can Cover the Cost of Living in San Francisco

Americans Gave a Record $617 Billion Last Year. The Retirees Who Wrote Checks Instead of Using This IRA Move Overpaid the IRS.