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Trump's New 401(k) Order, Two SSI Checks in August - and More
If your benefits and healthcare felt “in motion” this week, you’re not imagining it. SSI recipients are seeing two checks land in August (with a catch), Medicare insurers are trimming sails ahead of open enrollment, and there’s fresh chatter about private equity inside 401(k) target-date funds. Here’s what actually matters for your wallet and coverage—and what to do next.
By RetirementRedFlags.com
August 8th, 2025
Stay on top of these stories now to protect your savings, cut avoidable taxes, and keep your retirement plan on track.
1. Social Security: Why two SSI checks hit in August (and why September could feel tight)
Because Labor Day is Monday, September 1, the Social Security Administration is pushing September’s SSI payment forward into August. That means two SSI deposits in August (Aug 1 and Aug 29) and no SSI deposit in September. It’s a calendar quirk, not a bonus. Budget accordingly. Regular retirement benefits still follow the Wednesday schedule in August (generally Aug 13, 20, 27, based on birthdate). If you started benefits before May 1997, you’re on the 1st-of-month cadence.
Action Steps:
✔ Move the Aug 29 deposit into a separate “September” sub-account the day it arrives.
✔ Set bill pay dates now to avoid a September shortfall.
2. Trump’s 401(k) order: opening the door to crypto and private equity
President Trump signed an executive order directing regulators to clear a path for alternative assets—including private equity, real estate, and cryptocurrencies—to appear inside 401(k) plans. The move doesn’t force employers to add them; it signals DOL/SEC to rewrite guidance so plan sponsors and asset managers can package these exposures (likely inside managed accounts or target-date funds) without fearing ERISA blowback.
This could funnel a slice of America’s ~$9–12 trillion in 401(k) savings toward higher-fee, illiquid strategies (PE/credit) and volatile assets (crypto). Advocates say that can boost diversification and long-run returns; critics warn about complexity, pricing opacity, and payout/withdrawal frictions that don’t play nicely with retirees’ cash-flow needs. Expect marketing to ramp up before the rulemaking dust settles.
Action Steps:
✔ Watch for plan notices. Look for a Summary of Material Modifications, “Fund Changes,” or an updated target-date fund (TDF) fact sheet/prospectus.
✔ Open your plan’s Summary Plan Description and the TDF fact sheet. If the lineup starts adding crypto or private assets, read the fee table, liquidity/valuation notes, and risk section closely. Consider whether an age-appropriate index mix might suit you better.
3. Medicare: Insurers are tightening up—expect plan changes and fewer “extras”
The Wall Street Journal reports insurers are pulling back on Medicare—paring benefits, trimming plan choices, and exiting some markets—and Wall Street actually likes the discipline. Expect that tone to show up in the fall Annual Notice of Change (ANOC) mailers. Translation: fewer freebies, narrower networks, and higher out-of-pocket exposure in some areas.
This tracks with a broader reset in the sector: UnitedHealth has been warning about a tougher Medicare Advantage environment and a “generational pullback” in funding/utilization trends, and even Humana has signaled support for curbs on certain MA billing practices that have drawn scrutiny. All signs point to leaner plan designs ahead.
Action Steps:
✔ Prep for Medicare’s open enrollment (Oct 15–Dec 7)
✔ Watch for your ANOC in September/October.
✔ List your doctors, drugs, and hospitals; run them through the Medicare Plan Finder to see if a 2026 plan change would disrupt care/costs.
4. Confusion around Social Security rules is still widespread
A fresh pulse of coverage this week highlighted how many Americans remain fuzzy on Social Security basics—when to claim, how spousal/survivor benefits work, and what “trust fund depletion” actually means (spoiler: it doesn’t equal zero benefits).
If any of that sounds familiar, bookmark a checkup: compare your my Social Security statement, COLA history, and claiming options before making moves.
Action Steps:
✔ If your benefit was reduced for overpayment, call SSA to request reconsideration, a waiver, or a lower withholding rate (you don’t have to accept 50%). Document hardship.
If you have any questions about the headlines that hit the news this week, we are answering questions in our free Facebook group The Retirement Red Flags Community. Click below and we will make sure you get added.