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You should receive a 1099-R from both the state of Maryland and the state of Pennsylvania. You are wise to be making estimated tax payments. You should receive each statement in January of 2022. The 1099-R from Maryland should only cover January through April of 2021. The 1099-R from Pennsylvania should cover May through December of 2021.
https://sra.maryland.gov/sites/main/files/file-attachments/retireenewsjan2021_-_final.pdf?1610142338
You should not be assessed a late penalty. The IRS has a "pay as you go" system, which means you're supposed to pay taxes throughout the year as you earn or receive income, rather than sending a big lump sum to the IRS at the end of the year. If you are late with any given estimated, you may be subject to a penalty for that particular quarter. However, the IRS offers two "safe harbor" methods for determining whether you are subject to a penalty. If you meet one of these safe harbor amounts, the IRS won't charge an estimated tax penalty, even if you owe more than $1,000 at the end of the year.
The requirements are that you pay:
- 90% of the tax you owe for the current year. Estimate what you'll owe and pay at least 90% of this amount in four equal installments or through paycheck withholding.
- 100% (or 110%) of last year's tax bill. Pay 100% of the tax shown on your prior-year tax return before applying estimated payments, withholding, or refundable tax credits. If your adjusted gross income is more than $150,000 (or $75,000 if you're married and file a separate return from your spouse), the safe harbor is 110% of your prior-year tax.
Therefore, you will not be assessed a penalty if you meet either of the safe harbor methods above.
https://turbotax.intuit.com/tax-tips/irs-letters-and-notices/guide-to-irs-tax-penalties-how-to-avoid...
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