@oarcaute
It’s important that we all understand the precise terminologies to be used and what exactly you were doing. You mentioned a 401(k), an IRA, and a retirement plan from a school district.
401(k) plans and IRAs are completely different types of retirement accounts, they are controlled by different sections of the tax law, and have very different rules and procedures, even though they have a broadly similar purpose. Each other type of qualified workplace retirement plan is covered by a different section of the tax law. Some of them include 403B, 401(a), and 457.
You said “I continue to make monthly contributions after retirement with funds from my monthly Social Security payments”. It sounds like you are contributing to your workplace plan from a school district. If so, that is not a 401(k) or an IRA. Before we can understand the legality and the financial implications of what you have been doing, we need to understand exactly where you have been contributing your money, and exactly what kind of account it is. For example, for certain types of deferred compensation retirement plans, you would continue to receive a W-2, even after you’re retired. It also matters whether you have been making contributions by automatic deduction from your retirement pay or whether you have been sending checks out of pocket from your own funds.
