As you are preparing to file your taxes this year, we want to help make your life a little easier. Below, you’ll find a comprehensive guide with important dates, resources, and tips to help you complete your 2025 tax return. To start, here’s a handy checklist to organize your tax filing process.
At Pearl Planning, we are committed to assisting you and your tax professional in gathering the information needed for your tax return. Please don’t hesitate to contact us or have your Certified Public Accountant (CPA) or tax preparer reach out with questions. Once you’ve completed your tax return, clients are encouraged to securely upload a copy to us for a review of financial planning opportunities.
Raymond James 2025 Form 1099 Mailing Schedule
Get full information on Raymond James Tax Reporting.
Charles Schwab 2025 Form 1099 Mailing Schedule
Get full information on the product schedule
Fidelity 2025 Form 1099 Mailing Schedule
Get full information on Fidelity Tax Reporting
TIAA 2025 Form 1099 Mailing Schedule
Get full information on TIAA Tax Reporting
Altruist 2025 Form 1099 Mailing Schedule
Get full information on Altruist Tax Reporting
All custodians will mail 1099 tax statements by January 31st. The date your form will be produced typically depends on the complexity of the holdings in your account. We will notify you if we have information that your 1099 will be delayed until February 15th.
Important Update: How to Pay Taxes and Estimated Payments
The IRS no longer accepts paper checks for federal tax payments, including estimated tax payments.
All federal tax payments must now be made electronically using one of the following methods:
• IRS Direct Pay from a bank account
• Electronic Federal Tax Payment System (EFTPS)
• Debit card, credit card, or digital wallet through an IRS-approved provider
If you typically mail checks for estimated payments or balance due amounts, please plan to use an electronic payment option to avoid delays or penalties.
Mark Your Calendar Now for Important 2026 Dates
April 15: Deadline to file your tax return (or request an extension). Also, the last day to make 2026 IRA, Roth IRA, or HSA contributions (if you file on time). First-quarter tax estimates are due.
June 15: Second-quarter tax estimates are due.
September 15: Third-quarter tax estimates are due.
October 15: Deadline to file if you receive a six-month extension.
December 31: Deadline for required minimum distributions (RMDs) if over age 73, and the last day to make 2026 401(k)/employee plan contributions.
Viewing Your Tax Documents Online
Access online tax documents by signing into your respective custodian client access pages. Please contact our office if you need assistance.
Qualified Charitable Distributions (QCDs), Donor Advised Gifts, and Charitable Giving
If you completed QCDs in 2025, information about these will be included with your tax forms. QCDs are a tax-efficient way to give to charity and count toward your RMDs if you are eligible.
If you made gifts to a donor-advised fund, please inform your CPA and make sure to mention the cost basis and date you acquired shares if you gifted appreciated stock.
Keep receipts and details of charitable gifts and gather them for your tax preparation.
Tax Planning Opportunities for 2026 and Beyond
Adjust Withholdings: If you have had a significant change in income or need to review withholdings because of either big, unexpected tax bills or significant refunds, it’s likely time to review your tax withholdings. A conversation with your tax professional or financial planner might be warranted in order to assist.
Maximize Retirement Contributions: Ensure you’ve maximized contributions to 401(k)s, IRAs, and HSAs by the deadlines. IRA and HSA contributions can be made for the prior tax year up until the April filing deadline, while 401(k) contributions must be completed by December 31 of the calendar year.
Charitable Giving: Consider donor-advised funds or QCDs to maximize tax benefits.
Investment Strategies: Review your portfolio for tax-loss harvesting opportunities and assess capital gains planning strategies.
State-Specific Tax Credits: Check for education savings plan contributions or energy-efficient home improvement credits.
We hope you find this information helpful as you navigate the 2025 tax season. Please contact Pearl Planning for assistance—we’re here to collaborate with you and your tax professional to simplify the process and uncover valuable tax planning opportunities.
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