Yes, Marking These Financial Dates Early Will Help You Stay Ahead in 2025
Financial planning isn’t about waiting until the last minute or scrambling to meet deadlines. It’s about knowing what’s coming and preparing ahead so you can reduce stress, avoid penalties, and make smarter decisions for your money.
At Trail CPA, helping clients stay on top of important dates from estimated tax payments to enrollment periods is a key part of proactive financial planning. With 2025 underway, now is the perfect time to get these critical deadlines on your calendar.
Below are some of the key financial dates in 2025 that can impact your taxes, retirement planning, business compliance, and more.
Important Financial Dates for Individuals
January 1
The new tax year begins!
January 15
The final estimated tax payment for the prior tax year Q4 is due. Missing this deadline may result in penalties and interest.
April 1
Required minimum distributions begin for individuals who are required to take them.
April 15
This is one of the most important tax deadlines of the year. Federal income tax returns are due, as well as requests for filing extensions. This is also the deadline to make IRA and HSA contributions for the prior year, pay gift taxes, and submit the first quarterly estimated tax payment for the current year.
June 15
The second quarterly estimated tax payment for the year is due.
June 30
This is the final day to submit the FAFSA for the prior academic year.
September 15
The third quarterly estimated tax payment is due.
October 15
If you filed for a tax extension, your federal return must be submitted by this date.
November 1
Open enrollment begins for health insurance marketplace plans.
December 15
December 15 is the deadline to enroll in marketplace health insurance for coverage beginning January 1.
December 31
The tax year officially ends. Required minimum distributions must be completed, gifts must be finalized for tax purposes, and 401k employee contributions must be completed by this date.
Key Dates for Business Owners
January 15
Quarterly estimated tax payments for Q4 are due for individuals from pass-through business profits - sole proprietor, single-member LLC, S Corp & Partnership.
C Corps pay April 15, June 15, Sept 15, Dec 15
February 2 in 2026
Businesses must issue W-2 forms to employees and 1099 forms to contractors and vendors.
February 28 and March 31
These are the deadlines for filing various information returns, depending on whether forms are submitted by paper or electronically.
March 16 in 2026
S corporations and partnerships must file their tax returns or request extensions. This is also the deadline for distributing Schedule K 1 forms to owners.
April 15
C corporations and sole proprietors must file their tax returns or request extensions. The first estimated tax payment for the year is also due.
September 15
Extended returns for S corporations and partnerships must be filed by this date.
October 15
Extended returns for C corporations must be filed by this date.
December 15
The final estimated tax payment for many C corporations is due.
December 31
The calendar tax year ends for most businesses.
How Staying Ahead Helps
Knowing these dates in advance allows you to plan strategically instead of reacting at the last minute. Staying organized can help you avoid penalties, maximize retirement and education contributions, and coordinate healthcare and Medicare enrollments without unnecessary stress.
Should You Start Planning Now
If you want to reduce surprises and make smarter financial decisions throughout the year, planning ahead is absolutely worth it. At Trail CPA, we work closely with clients to stay ahead of deadlines, identify opportunities, and keep everything running smoothly.
If you would like help organizing these dates or understanding how they apply to your specific situation, we are always here to help.