The TS/SCI Tax Calendar: Key Dates for Cleared Professionals

Key takeaways

• Cleared professionals have a reason beyond penalties to file and pay on time: unresolved tax problems can raise concerns in a security clearance review.
• W-2 contractors, 1099 contractors, and business owners face different deadlines. Self-employed contractors generally owe quarterly estimated taxes.
• The dates below are federal. They can shift for weekends, holidays, or disaster relief, and your state may differ.
• Year-end moves, like retirement contributions, must usually happen by December 31, not at tax time.
• A short calendar reminder now is cheaper than a penalty or a clearance conversation later.

If you hold a Top Secret or TS/SCI clearance, taxes are not just a money question. Security reviews look at financial responsibility, and failing to file or pay taxes is one of the issues that can come up. On top of that, many cleared professionals are contractors with variable pay, per diem, or side income, which means the deadlines are not always the same as a typical W-2 employee's.

This calendar covers the key federal dates from now through September 2027, with a note on who each one applies to.

Why Taxes Matter for Cleared Professionals

The federal guidelines used to evaluate eligibility for access to classified information include a financial considerations factor. Delinquent debts, unfiled returns, and unpaid taxes are the kinds of things that can draw attention there. A problem is not automatically disqualifying, and adjudicators look at the full picture and how you handled it, but staying current is the simplest way to avoid the conversation.

If you already have a tax issue, such as an unfiled return or a balance you cannot pay, address it early. A tax professional can help you set up a resolution, and your facility security officer or a clearance attorney can advise on any reporting questions.

Key Dates at a Glance

October 15, 2026: Extended Return Deadline

If you requested an extension for your 2025 federal return, this is the new filing deadline. An extension to file is not an extension to pay. Any tax owed was still due in April.

December 31, 2026: Year-End Planning Deadline

Many of the moves that affect your 2026 tax bill have to be done by the end of the calendar year, including:

• Employee contributions to a 401(k) or the Thrift Savings Plan, which generally need to come through payroll by year-end
• Roth conversions
• Required minimum distributions, if you are subject to them
• Charitable gifts you want counted for 2026

This is also a good time to check whether your withholding or estimated payments are on track so you are not surprised in April.

January 15, 2027: Fourth-Quarter Estimated Payment

If you are a 1099 contractor or business owner, the final 2026 estimated tax payment is due. Estimated payments are how self-employed people pay income and self-employment tax throughout the year, since no one is withholding for you.

Around February 1, 2027: W-2s and 1099s

Employers and clients must furnish W-2 and 1099-NEC forms by January 31. In 2027 that date falls on a Sunday, so the deadline moves to the next business day. If you are a contractor who pays others, this is your filing deadline too. If you are waiting on forms, this is when to follow up.

April 15, 2027: Filing Deadline and More

Several things land on the same day:

• Your 2026 federal return is due, or you must file for an extension
• Any tax you owe for 2026 is due
• The first-quarter 2027 estimated payment is due
• The deadline to make 2026 contributions to a traditional or Roth IRA or an HSA

June 15, 2027: Second-Quarter Estimated Payment

The second 2027 estimated payment for self-employed contractors.

September 15, 2027: Third-Quarter Estimated Payment

The third 2027 estimated payment. The fourth follows in January 2028.

Which Dates Apply to You?

• W-2 contractor or employee: Your employer withholds tax, so your main dates are the filing deadline and year-end contribution deadlines. Review your withholding if your pay or bonus changed.
• 1099 contractor or consultant: You likely owe quarterly estimated payments and self-employment tax, and you should keep clean records of income and expenses.
• Business owner: Your entity type affects your return and deadlines, so confirm them with your CPA.
• Mixed income: Many cleared professionals have a W-2 job plus consulting income. Withholding at the day job can sometimes be adjusted to cover side income, which is worth discussing with a tax professional.

Per Diem, Travel, and Records

Many cleared contractors travel or receive per diem. How those payments and costs are treated for tax purposes depends on how you are paid and the details of your assignment, so ask a tax professional how yours should be handled and keep your records organized throughout the year.

Frequently Asked Questions

Can a tax problem affect my security clearance?

It can be a factor. Failing to file returns or pay taxes is the kind of financial issue that can come up in a clearance review. How you respond and resolve it matters.

Do 1099 contractors really have to pay taxes quarterly?

Generally yes, if you expect to owe a meaningful amount of tax for the year. Estimated payments are how self-employed people stay current, and missing them can result in penalties.

What if I cannot pay what I owe by the deadline?

File on time anyway and contact the IRS about payment options. Filing late adds separate penalties.

Is the TSP contribution deadline the same as the IRA deadline?

No. TSP and 401(k) employee contributions generally have to be made through payroll by December 31. IRA contributions for a given year can usually be made until the filing deadline the following April.

Does RPM Financial Group prepare tax returns?

No. RPM works alongside your CPA or tax preparer so your plan accounts for tax strategy, retirement, and cash flow together.

How RPM Financial Group Can Help

RPM Financial Group, led by Ryan P. McGonigal, works with cleared professionals, government contractors, and federal employees across the DC Metro area and nationwide. If you would like to talk through your planning, book a free 20 minute call.

This article is for general educational purposes only and is not tax, legal, or investment advice. Deadlines and rules change and depend on your situation, so confirm dates at IRS.gov and consult a qualified tax professional.