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Not the Only One Checking His List

December 5, 2025 by Jason P. Tank, CFA, CFP, EA

There is still a little bit of time to cross a few things off your list. No, I’m not talking about your Christmas list.

To start, if you’re going to be spending time with aging family members, think about doing a cybersecurity audit. It’s not very festive, I know. But the holidays are sometimes the only moment we get to handle things face-to-face.

My number one recommendation is to help them set up and learn to use Apple’s new Passwords app. It works across all their Apple devices and it uses Face ID or Touch ID to help them easily access their new strong passwords. Besides retiring the use of a bunch of repeated and possibly compromised passwords, the very best feature of this new app is that it makes password sharing super easy.

Of course, try to tackle the login credentials that matter most – their banks, credit cards, investment accounts and also their email account. Beyond setting up some unique and strong passwords, be sure to check that each of these key accounts have two-factor authentication enabled. While this whole process isn’t a simple one – for those of you who know – trying to fix a problem remotely is way harder.

Switching gears to the upcoming tax season. For those wise enough to donate to charities directly from their IRA – and not their regular checkbook – remember that your Form 1099-R won’t actually report those donations any differently than normal distributions. In other words, it doesn’t split out your charitable activities. So, if you forget to tell your tax preparer about your IRA donations, you’ll end up paying taxes you don’t owe.

Thankfully, starting with the 2026 tax season, brokerage firms will be required to actually split out your IRA donations on your Form 1099-R. I’ve been asking for that for years and I couldn’t be happier. But, for 2025, we’re not yet there. So, remind yourself to tally them up and report them to your tax person.

Finally, the new tax law offered up a change for those over age 65. Unless you make too much money, you are getting a new “senior deduction” that adds $6,000 on top of your large standard deduction. You can double that to $12,000, if you’re married. This change opens up more room in the lower tax brackets and it means you should review a few tax moves before New Year’s Eve.

At the very least, you should take a look at taking some extra IRA distributions at low tax rates. Better yet, you might even upsize your Roth conversion strategy. Best of all, it’s possible you can realize some long-term capital gains – effectively resetting your cost basis – and owe zero federal tax. Be careful, though, each of these moves might take some number crunching to get things just right. The tax code is not as easy as it should be and, unfortunately, it’s gotten more complicated.

Can We Square The Circles?
HSAs and Capital Gains

About Jason P. Tank, CFA, CFP, EA

Jason is the founder of Traverse City, Michigan-based Front Street Wealth Management, the independent, fee-only wealth advisory firm for individuals, families and trusts who value proactive management of their investments and a deeper confidence in their wealth.

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