Episode 52 of Retirement Tax Matters launches a two-part autumn series focused on year-end tax planning for high-net-worth pre-retirees in the $2M to $8M space. Garrett Crawford, CFP® professional, and Adam Reed discuss why running a fall income tax projection is the most essential step working pre-retirees fail to complete each year. They break down how auditing a mid-year W-2 paystub helps verify federal tax withholding, catch bonus timing shifts, and prevent IRS estimated tax underpayment penalties before the December 31st deadline.

We have developed a 5-step framework for what tax planning looks like for High-Net-Worth Retirees between $2M-$8M. It walks you through each season of the calendar year and how we implement tax-return driven financial planning for clients. Request a free resource using this link: https://www.retirementtaxmatters.com/checklist

00:00 Introduction to Year-End Tax Planning & Pre-Retiree Strategy
02:18 The Pre-Retiree Challenge: High Income & Large Portfolios ($2M-$8M)
03:32 The #1 Tax Mistake: Waiting Until April to Calculate Final Income
04:58 Safe Harbor Traps with Q3 & Q4 Quarterly Estimated Taxes
06:15 Why Your Pay Stub May Be Another Overlooked Tax Planning Document
09:44 Managing Brokerage Accounts, Dividend Reinvestments & Phantom Income
12:44 Bracket Creep vs. Scaling Back: Strategic Roth Conversions While Working
13:54 Implementing a "Season of Pause" in November & December
16:58 Action Steps: DIY Tax Planning vs. Delegating to a CFP®

Visit us online at: https://www.retirementtaxmatters.com

Review our required industry disclosures here: https://www.retirementtaxmatters.com/disclosures

Episode 51 of Retirement Tax Matters addresses how high-net-worth retirees in the $2M to $8M range should evaluate managing a six-figure Health Savings Account during retirement. Garrett Crawford, CFP® professional and Adam Reed break down the trade-off between saving an HSA for late-in-life tax-free compounding versus spending those funds earlier to pay qualified health expenses. The conversation examines the administrative hassle of maintaining decades of medical receipts, highlighting why trying to over-optimize account mechanics into your 80s can create unnecessary friction for adult children and healthcare powers of attorney.

We have developed a 5-step framework for what tax planning looks like for High-Net-Worth Retirees between $2M-$8M. It walks you through each season of the calendar year and how we implement tax-return driven financial planning for clients. Request a free resource using this link: https://www.retirementtaxmatters.com/checklist

00:00 Introduction to HSAs in Retirement Planning
01:18 The Shoebox Method vs. Return on Hassle
07:08 Integrating HSAs with Long-Term Care Planning
13:28 IRS Limits for HSA Long-Term Care Premium Payments
15:35 Rules and Pitfalls of Inheriting an HSA
18:20 Itemized Medical Deductions (7.5% AGI) vs. Saving Your HSA

Visit us online at: https://www.retirementtaxmatters.com or https://www.providenceadvisors.com

Review our required industry disclosures here: https://www.retirementtaxmatters.com/disclosures

In Episode 50 of Retirement Tax Matters, Garrett Crawford, CFP® professional, and Adam Reed review the latest numbers from the Social Security Trust Fund report and what projected 2032 reserve depletion means for retirees with $2M to $8M portfolios. They break down why ongoing payroll tax collections still cover approximately 78% of scheduled benefits even if reserve funds run out, and why modeling Social Security at zero creates an artificial gap that can lead retirees to trade valuable time by working longer than needed. Garrett also shares his perspective on potential Congressional fixes and explains how an annual tax-return-driven process helps high-net-worth families keep headlines in perspective and protect their multi-year drawdown plan.

We have developed a 5-step framework for what tax planning looks like for High-Net-Worth Retirees between $2M-$8M. It walks you through each season of the calendar year and how we implement tax-return driven financial planning for clients. Request a free resource using this link: https://www.retirementtaxmatters.com/checklist

Timestamps
00:00 Introduction & Social Security Unease
02:26 Breaking Down the 2025 Social Security Trust Fund Report
05:19 Depletion in 2032 & The 78% Benefit Reality
07:31 Potential Fixes: Tax Hikes vs. Benefit Cuts
08:52 What Social Security Depletion Means for $2M–$8M Retirees
12:57 Why Planning for $0 in Social Security Is a Mistake
14:26 Will Congress Cut Benefits? Predictions & Tax Return-Driven Planning

Visit us online at: https://www.retirementtaxmatters.com
Review our required industry disclosures here: https://www.retirementtaxmatters.com/disclosures