Taxes

Harry Sit has written an article on his website, The Finance Buff, this morning 9/14/2026, describing the new requirement for using ID.me to log into a TreasuryDirect account. I found the article particularity informative as, like him, I had previously obtained a ID.me account.
His closing comment, “You have two bad choices. Either give sensitive information to a private company picked by the government agency or sell everything and pay taxes. I really don’t like this,

My wife and I are 73 and 75 and in RMD territory. With pension, SS and RMD our marginal tax bracket is 24%.
80% of our assets are in tax sheltered IRAs. Other than QCDs to reduce tax liability are there any other strategies? We recognize that one of us will be facing the widow/widower’s tax situation. Also IRMAA will take a bigger chunk of our Medicare bill.
My feeling is that we continue with our current situation and pay the effective tax rate of maybe 18 –

THE CHOICE BETWEEN a traditional retirement account or a Roth is a frequent topic on HumbleDollar. The choice is generally framed as a choice between paying taxes up front (a Roth), or deferring taxes until withdrawal (traditional). I thought it would be interesting to evaluate a real-life example of how this choice might work out.
In December of 2016 my wife and I had an opportunity to each open a Roth IRA. My wife took a partial sabbatical that year,

The US Treasury Department announced that the debt has increased to 40 Trillion dollars. In the articles explaining the debt, I keep reading about how Social Security payments are adding to the debt. Can someone please explain to me how that is? My understanding is the payments are made from collections of  Social Security taxes from current employees and employers, as well as taking money from the Social Security trust fund. So please explain how a self funded program adds to the deficit.

If you are expecting a 2025 tax refund that has not yet arrived and/or you have received a IRS CP53E notice then the Taxpayer Advocate Service has the following guidance –
There has been a lot of information in the news about how the IRS is moving away from paper checks. While direct deposit is a safe and secure way to get your tax refund, there are scammers out there looking to capitalize on any confusion about updating your bank account information.

This post is an extension of Rick’s and Richard’s recent posts regarding taxes in retirement. 
A recurring issue I dealt with as a tax preparer was calculating a (unpleasant) surprise the first year that someone retired. While working, the employee typically gets a paycheck with adequate tax withholding. When he leaves the job behind for the greener pastures of retired life, things can get a little more complicated. Now, instead of a single W2 to deal with,

A recent post about the taxation of Social Security (SS) benefits provided an example of the complexity of the way that SS benefits are taxed, and how they interact with other sources of income. I’ve read innumerable articles on this complexity, and experienced it first hand while preparing hundreds of tax returns for AARP TaxAide. Clients were frequently surprised and confused by this.
The referenced post’s example posits a couple, 65+, MFJ tax status, with $50,000 in combined SS benefits.

Per the TreasuryDirect website –
https://www.treasurydirect.gov/savings-bonds/idme-one-month/
ID.me will replace your TreasuryDirect traditional login and will be required after October 28, 2026.
As was noted today on the Boglehead’s Forum if you have holdings directly with the US Treasury and decide to and are able to sell all such holdings before the login change over you would still need to be able to login in 2027 to get your 2026 tax documents like 1099-Int., etc.

Complaining about taxes is not unique to seniors or in my case maybe a super senior, but they are mighty vocal and prolific on the internet. I was curious, how much could a age 65+ couple earn in retirement before actually paying federal income taxes on their money?
I ran a couple of scenarios using AI tools. I was a bit shocked at the results. Here is an example …
I asked what a couple both age 65 + with combined SS benefits of $50,000,

EVERY ARTICLE ABOUT Roth conversions says the same thing: pay the tax from taxable money, not from the IRA.
That is good advice if you have taxable money.
Plenty of retirees do not. Their savings sit almost entirely in a traditional IRA, built from years of 401(k) contributions and a rollover at retirement, with little brokerage money and no cash reserve worth naming.
For them, “pay from outside money” is not advice. It is a condition they do not meet.

AFTER YEARS OF heady gains in the stock market, many investors are facing the same question: To manage risk, they’d like to cut back on one or more of their holdings. But because of the potentially costly tax bill that might result, they aren’t sure exactly how to do that.
How can you square this circle?
One easy option would be to donate appreciated assets to charity. But that would make sense only if it aligns with your charitable goals and,

Along with changes to the application of the COLA there is discussion about changing the way and amount of income taxes applied to SS benefits.
It’s quite complex, but here is a link to some alternatives from the Committee for a Responsible Federal Budget. https://www.crfb.org/papers/new-approaches-social-security-benefit-taxation

THE WIDOW TAX is sold to the wrong households. It gets pitched to affluent couples as the reason to convert to a Roth or buy life insurance. The pitch says that when one spouse dies, the survivor files single, lands in a higher bracket, and gets clobbered. I ran the numbers for three couples at three incomes, and at the comfortable end the widow tax often costs nothing, or even less than nothing.
The real cost lands lower down,

Have any HumbleDollar readers who are subject to IRMAA filed a tax return more than 2 years late? If so, I’d love to hear your experience.

I read this article from Kiplinger online about the four ways couples should prepare for the Widow’s Penalty.
https://www.kiplinger.com/taxes/tax-planning/how-to-prepare-for-the-widows-penalty
The article states that in an unfortunate twist of the tax system, losing a spouse may trigger a huge financial hit called the widow’s penalty.  The good news – you can plan for it.  It is a good read. Your thoughts and your plan.