Three critical retirement planning deadlines arrive before 2027. Missing these windows locks in permanent tax consequences for your portfolio. As we approach these dates, the decisions surrounding your 401k and specific Roth conversions become irreversible. Once the calendar turns, the rules governing your assets and coverage shift, potentially impacting your long-term financial stability if the sequence of actions is not managed correctly. This breakdown focuses on the correct order of operations for these specific Medicare deadlines to ensure you avoid negative outcomes. Failing to align your strategy with these regulatory shifts can create unnecessary complications for your future income. Subscribe for weekly financial strategy breakdowns, and comment which retirement topic you want us to analyze next.