One post tagged with "deadlines"

Thinking about electing S-corp tax status? Great—just don’t miss the clock. The S-corp election can be a powerful tax-saving tool for small business owners, but its deadlines are strict and non-negotiable. Missing one can complicate your tax picture significantly.

Here’s the practical, accountant-approved version of what you need to know, plus how to track it all cleanly in your Beancount ledger.

The Deadline, In One Bite​

The most critical date is for filing Form 2553, Election by a Small Business Corporation. This is the form that tells the IRS you want to be taxed as an S-corp.

• For existing, calendar-year businesses: You must file Form 2553 by the 15th day of the 3rd month of the tax year you want the election to take effect. For a 2025 election (effective January 1, 2025), the deadline is Saturday, March 15, 2025. Because this falls on a weekend, the IRS weekend/holiday rule pushes the functional deadline to the next business day: Monday, March 17, 2025.
• For new businesses: If this is your business's first tax year, you have “2 months and 15 days” from the start of your tax year to file. The exact date depends on when your tax year officially begins. For example, if your business starts on January 7, your deadline would be March 21.

Tip: If your business operates on a fiscal year rather than a calendar year, the same logic applies. Calculate your deadline as the 15th day of the 3rd month from your fiscal year's start date.

What If You Missed It?​

Don't panic. The IRS understands that business owners can miss deadlines. If you intended to elect S-corp status but failed to file on time, you may be eligible for late-election relief.

The IRS provides a streamlined procedure, Revenue Procedure 2013-30, which allows many small businesses to request retroactive S-corp status. You generally qualify if you can show you had reasonable cause for filing late and meet the procedure's other requirements.

Other Key Dates Tied to S-Corps​

Once you're an S-corp, the deadlines don't stop. Here are two other important dates to mark on your calendar:

• 1120-S Filing (The S-corp Tax Return): Your annual S-corp tax return, Form 1120-S, is due by the 15th day of the 3rd month after your tax year ends. For most businesses (calendar-year filers), this is the same as the election deadline: March 17, 2025.
• Need More Time? If you can't file your 1120-S on time, you can file Form 7004 for an automatic 6-month extension. This extends the deadline to file your return to September 15. Crucially, this is an extension to file, not an extension to pay. Any taxes you owe are still due by the original March deadline.

Who Should Even Elect S-Corp?​

S-corp status isn't for everyone. Its primary benefit is reducing self-employment taxes. It achieves this by allowing you to split your business's profit into two categories:

1. Reasonable W-2 Wages: This is a salary you pay yourself, which is subject to standard payroll taxes (Social Security and Medicare).
2. Shareholder Distributions: This is the remaining profit you take from the business, which is not subject to self-employment tax.

However, this advantage comes with added complexity and costs. S-corps require running formal payroll, adhering to "reasonable compensation" standards set by the IRS, and handling more compliance paperwork, like filing Forms 1120-S and issuing K-1s to shareholders.

Before you make the jump, run the math. A CPA can help you model the breakeven point where the tax savings outweigh the additional administrative costs.

Make the Deadline Easier—with Beancount​

A well-maintained ledger is your best friend for S-corp compliance. You can use Beancount to stay on top of deadlines and clearly distinguish between wages and distributions.

Minimal Chart of Accounts (Starter)​

Here's a basic chart of accounts to get you started:

• Assets:Bank:Checking
• Income:Sales
• Expenses:Payroll:Wages
• Expenses:Payroll:EmployerTaxes
• Equity:Distributions ← For shareholder draws
• Equity:Opening-Balances

Typical Postings​

Your Beancount entries will create a clear separation between payroll expenses and equity distributions.

; W-2 payroll is a business expense
2025-02-28 * "Run payroll - February"
  Assets:Bank:Checking                 -6200 USD
  Expenses:Payroll:Wages                5000 USD
  Expenses:Payroll:EmployerTaxes        1200 USD
  ; entity: S-Corp  period: 2025-02

; Shareholder distribution is a draw on equity, not an expense
2025-03-10 * "Shareholder distribution"
  Assets:Bank:Checking                 -3000 USD
  Equity:Distributions                  3000 USD
  ; entity: S-Corp  period: 2025-Q1

Useful Guardrails (Queries & Tags)​

Use Beancount's features to sanity-check your finances and ensure you're meeting reasonable compensation standards.

• Tag every owner draw with something memorable, like distrib: "yes".
• Periodically run a query to compare total wages paid against total distributions taken.

You can run a quick check from your terminal with bean-query:

SELECT account, SUM(position)
WHERE (account ~ 'Expenses:Payroll:Wages' OR account ~ 'Equity:Distributions')
AND year = 2025
GROUP BY account;

This will give you a clean summary of your wages and distributions for the year, helping you and your CPA assess if your salary is "reasonable."

Paper Trail for the Election​

Keep your S-corp documentation organized and linked to your ledger.

• Create a docs/ folder in your Beancount directory to store PDFs of your signed Form 2553, the IRS acceptance letter, any late-election relief statements, and your payroll setup documents (EIN, state IDs).
• Record a note transaction in your ledger the day you file the election. This creates a permanent, dated record.

2025-01-22 note "Filed IRS Form 2553 for S-corp election (effective 2025-01-01)"

Edge Cases to Watch​

• Your "first tax year" start date might not be your formation date. The clock for the "2 months and 15 days" deadline starts when your company has shareholders, acquires assets, or begins business operations—whichever comes first.
• For non-calendar fiscal years, be precise. Your Form 2553 deadline is based on your fiscal year's start date, while your Form 1120-S deadline is based on its end date.

Quick Checklist​

Ready to proceed? Here is a final checklist to guide you.

✅ Decide if the S-corp structure fits your business based on profit level, payroll readiness, and state-specific rules. ✅ Calendar Form 2553 with the correct deadline (and set a one-week reminder for yourself). For 2025, that's March 17, 2025. ✅ If you're late, immediately evaluate if you qualify for relief under Rev. Proc. 2013-30. ✅ Configure your payroll system and map the new expense and equity accounts in your Beancount ledger. ✅ Prepare to file Form 1120-S by the deadline or file Form 7004 for an extension.

This guide provides general information, not tax advice. Every business situation is unique. Please consult with your CPA to determine the best course of action for your specific circumstances.