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How S Corporation Owners Can Deduct Health Insurance Premiums

· 6 min read
Mike Thrift
Mike Thrift
Marketing Manager

If you operate as an S corporation, understanding how to properly handle health insurance premiums can save you thousands in taxes each year. However, the rules for S corp owners are different from other business structures, and getting it wrong could cost you deductions or trigger an audit.

The 2% Shareholder Rule: What You Need to Know

2025-11-03-how-s-corporation-owners-can-deduct-health-insurance-premiums

The IRS has a special rule for S corporation shareholders who own more than 2% of the company. Unlike regular employees, these shareholders cannot receive health insurance as a tax-free fringe benefit. Instead, any premiums paid on their behalf must be reported as taxable wages.

This might sound like bad news, but there's a silver lining: both the S corporation and the shareholder can still benefit from tax deductions, just through a different process.

How It Works: The S Corp's Perspective

When your S corporation pays health insurance premiums for a more-than-2% shareholder, here's what happens:

The company can deduct the premiums as a business expense, similar to how it would deduct regular wages. This reduces the S corporation's taxable income.

The premiums must be added to the shareholder's W-2 wages in Box 1 (taxable wages). However, these amounts are not subject to Social Security and Medicare taxes (FICA) or federal unemployment taxes (FUTA), which provides some payroll tax savings.

The S corporation must have established the health insurance plan and pay the premiums directly or reimburse the shareholder under an accountable plan.

How It Works: The Shareholder's Perspective

As a shareholder-employee, you'll report the health insurance premiums as income on your W-2, but you can claim them back through the self-employed health insurance deduction on your personal tax return (Form 1040, Schedule 1).

This deduction is considered "above-the-line," meaning you can claim it even if you don't itemize deductions. This is valuable because it:

  • Reduces your adjusted gross income (AGI)
  • Lowers your overall tax liability
  • May qualify you for other income-based tax benefits

The net effect is that you essentially break even on the income taxes for the premiums, while the S corp saves on payroll taxes.

S Corporations With Only Shareholder-Employees

If your S corporation has no employees besides the shareholders, you cannot establish a group health insurance plan. Instead, you must:

  1. Purchase an individual or family health insurance policy in your own name
  2. Have the S corporation reimburse you for the premiums, or have the corporation pay the premiums directly
  3. Report the premiums as wages on your W-2
  4. Claim the self-employed health insurance deduction on your personal return

This arrangement still provides tax benefits, but requires careful documentation to ensure the IRS accepts your deductions.

S Corporations With Non-Shareholder Employees

When your S corporation has employees who are not shareholders, you can establish a group health insurance plan. Non-shareholder employees can receive health insurance as a tax-free benefit, just like employees of any other company.

Shareholders can be included in this group plan, but the special rules still apply:

  • Premiums for shareholders must be reported as taxable wages on their W-2
  • Shareholders claim the self-employed health insurance deduction on their personal returns
  • Non-shareholder employees receive the benefit tax-free

This creates a two-tier system within your health insurance plan, which requires careful administration and record-keeping.

Important Requirements and Limitations

To successfully claim health insurance deductions as an S corp owner, you must meet several requirements:

The S corporation must pay the premiums. You cannot pay premiums personally and then try to deduct them as a business expense. The corporation must either pay the insurance company directly or reimburse you through a proper reimbursement arrangement.

You cannot deduct more than you earn. The self-employed health insurance deduction is limited to your net earnings from the S corporation. If your wages are 50,000butyourpremiumsare50,000 but your premiums are 60,000, you can only deduct $50,000.

Proper documentation is essential. Keep records of all premium payments, W-2 reporting, and reimbursement arrangements. The IRS scrutinizes these deductions, so good record-keeping is crucial.

Timing matters. The S corporation must establish the health insurance plan during the tax year, and you must be actively engaged in the business to claim the deduction.

Practical Steps for Implementation

If you want to start taking advantage of health insurance deductions as an S corp owner, follow these steps:

  1. Choose the right health insurance plan. If you have non-shareholder employees, research group plans. If you're a solo owner, shop for individual plans that meet your needs.

  2. Set up a payment or reimbursement system. Decide whether the S corporation will pay premiums directly to the insurance company or reimburse you. Document this arrangement clearly.

  3. Coordinate with your payroll provider. Ensure they understand that health insurance premiums must be added to shareholder W-2 wages but excluded from FICA and FUTA calculations.

  4. Track everything carefully. Maintain records of all premium payments, reimbursements, and insurance policy documents.

  5. Work with a tax professional. Given the complexity of these rules, having a qualified accountant or tax advisor review your setup can prevent costly mistakes.

Common Mistakes to Avoid

Many S corp owners make these errors when handling health insurance:

Failing to report premiums on the W-2. This is one of the most common mistakes. If you don't add the premiums to your W-2 wages, the IRS may disallow your deduction entirely.

Trying to take the deduction without proper S corp action. The corporation must formally establish and pay for the insurance plan. Personal payments that aren't properly reimbursed don't qualify.

Confusing the self-employed health insurance deduction with itemized medical expenses. These are different deductions with different rules and limitations.

Not adjusting for the deduction when calculating estimated taxes. Since the deduction reduces your AGI, it should factor into your quarterly estimated tax payments.

The Bottom Line

While S corporation health insurance rules are more complex than those for sole proprietors or partnerships, they still offer significant tax advantages. By properly structuring your health insurance arrangement and maintaining accurate records, you can reduce both your corporate and personal tax liability.

The key is understanding that health insurance premiums flow through two tax returns—first as a deduction for the S corporation and wages for the shareholder, then as a deduction on the shareholder's personal return. When handled correctly, this creates a win-win situation that reduces your overall tax burden while providing essential health coverage for you and your family.

Remember, tax laws change regularly, and your specific situation may have unique considerations. Always consult with a qualified tax professional to ensure you're maximizing your deductions while remaining fully compliant with IRS regulations.

S Corp vs. C Corp: Advantages and Disadvantages for Beancount.io Users

· 11 min read
Mike Thrift
Mike Thrift
Marketing Manager

Choosing the right business entity is one of the most critical decisions a founder makes. It impacts your taxes, your ability to raise money, and your administrative workload. Two of the most common structures for incorporated businesses are the C corporation and the S corporation. What’s the difference, and which one is right for you?

TL;DR

2025-08-11-s-corp-vs-c-corp-advantages-and-disadvantages

C corporations are taxed at the corporate level, and shareholders are taxed again when they receive dividends—a system known as double taxation. S corporations are "pass-through" entities, meaning profits are taxed just once on the owners’ personal tax returns, but they come with strict ownership limits. If you plan to reinvest heavily and raise venture capital, the C corp is often the cleaner, more scalable choice. If you're a profitable, owner-operated business and want to distribute cash while paying yourself a reasonable salary, an S corp can significantly lower your tax bill.

Either way, Beancount.io is built to keep your books clean with plain-text, auditable entries and export-ready financials that make tax time a breeze.


Quick Comparison

TopicC corporationS corporation
How to createFile articles of incorporation with a state (this is the default status).Incorporate first, then file IRS Form 2553 to elect S corp status.
TaxationDouble taxation: Profits are taxed at the corporate level, then shareholders are taxed on dividends.Pass-through: Income is taxed on the owners’ personal returns (no corporate income tax).
Ownership rulesNo limits on the number or type of shareholders; multiple classes of stock are allowed.≤100 shareholders, who must be U.S. persons only, and only one economic class of stock is permitted.
Investor perceptionVC-friendly, especially the Delaware C corp, which is the industry standard.Less attractive to VCs due to pass-through taxation and stock class limitations.
Best forHigh-growth startups focused on reinvestment and raising external capital.Owner-operators who want to pull cash from the business via a mix of payroll and distributions.
Core IRS forms1120, 1120-W, 941, 1099-DIV (if paying dividends).1120-S, 1120-W (if applicable), 941, Schedule K-1 issued to each owner.

Note: The federal corporate income tax is a flat 21%. However, state rules for both C corps and S corps vary widely. Always verify the tax treatment in your state of incorporation and operation.


What is a C Corporation?

A C corporation is the standard, default corporate structure in the United States. When you file articles of incorporation with a state, you create a C corp unless you elect otherwise. This structure provides limited liability protection for its owners (shareholders), requires formal governance (a board of directors, officers, bylaws), and creates a legal entity that investors and banks recognize and understand.

How C Corps Are Taxed

C corps have a distinct tax identity. They file their own corporate tax return, IRS Form 1120, and pay taxes on their net income at the corporate level. If the corporation then distributes its after-tax profits to shareholders in the form of dividends, those shareholders must report that dividend income on their personal tax returns and pay taxes on it again. This is the "double taxation" C corps are known for.

Why Choose a C Corp?

  • Fundraising & Equity: This is the biggest draw for startups. C corps can issue multiple classes of stock (e.g., common and preferred), which is essential for venture capital deals. Structuring option pools, SAFEs, and convertible notes is straightforward.
  • Reinvestment: If you plan to plow all your profits back into growing the business, you can avoid the second layer of tax by simply not paying dividends. The profits are taxed once at the corporate rate and remain in the company.
  • Signaling: For better or worse, incorporating as a Delaware C corp signals to investors that you intend to build a venture-scale company.

Drawbacks of a C Corp

  • Double Taxation: The primary disadvantage. If you plan to distribute profits regularly, you’ll pay tax twice on the same dollar.
  • Administrative Burden: C corps come with more compliance requirements, including holding board meetings, maintaining corporate minutes, and handling more complex state and federal filings.
  • Limited Deductions: Certain tax credits and deductions available to individuals or pass-through entities are not available at the corporate level.

What is an S Corporation?

An S corporation is not a different type of legal entity but rather a special tax election made with the IRS. A domestic corporation (or an LLC that elects to be taxed as a corporation) can file to become an S corp, which allows it to be treated as a pass-through entity for federal tax purposes.

Eligibility Snapshot

To qualify for and maintain S corp status, a company must meet strict criteria:

  • Have no more than 100 shareholders.
  • All shareholders must be U.S. individuals, certain trusts, or estates. No corporations, partnerships, or non-resident aliens can be shareholders.
  • Have only one class of stock economically. (Differences in voting rights are allowed, but all shares must have the same rights to profits and assets).
  • Not be an ineligible corporation, such as a bank or insurance company.
  • You must file Form 2553 on time. For an existing business, this is generally by the 15th day of the third month of the tax year (March 15th for a calendar-year business).

Why Choose an S Corp?

  • Single Layer of Tax: Profits and losses "pass through" the business directly to the owners' personal tax returns, reported via a Schedule K-1. The corporation itself does not pay federal income tax.
  • Self-Employment Tax Savings: This is a key benefit. Owner-employees must pay themselves a "reasonable salary," which is subject to FICA taxes (Social Security and Medicare). However, any additional profits can be paid out as distributions, which are not subject to self-employment taxes.

Drawbacks of an S Corp

  • Strict Rules: The ownership restrictions are rigid. Accidentally violating one (e.g., selling stock to an ineligible shareholder) can lead to an "inadvertent termination" of S corp status, which can have messy tax consequences.
  • "Reasonable Compensation" Scrutiny: The IRS pays close attention to whether the salary paid to owner-employees is reasonable. Paying yourself an artificially low salary to maximize tax-free distributions is a major red flag for an audit.
  • State Variability: Not all states recognize the S corp election. Some tax S corps as if they were C corps, or they may impose a separate entity-level tax, partially negating the federal tax benefit.

Which Should You Pick?

The decision boils down to your goals for ownership, funding, and cash flow.

Consider a C corp if you expect to:

  • Seek institutional investment from venture capitalists.
  • Create different classes of stock for founders and investors (e.g., preferred shares).
  • Use complex equity instruments like SAFEs or convertible notes.
  • Have non-U.S. owners, either now or in the near future.
  • Reinvest profits for several years before taking significant cash out of the business.

Consider an S corp if you:

  • Are 100% owned by U.S. individuals who meet the criteria.
  • Are already profitable and want to distribute cash to owners efficiently.
  • Can confidently run payroll and pay owner-operators a defensible, market-rate salary.
  • Do not need complex equity classes for different types of owners.

If you’re unsure, many businesses start as a Delaware C corp to maintain maximum flexibility. You can evaluate making an S corp election later if your profitability and ownership structure make it advantageous.


Beancount.io: How Your Books Differ (with Examples)

Whether you choose a C or S corp, Beancount.io’s plain-text ledger makes the flow of money for taxes and equity explicit and auditable. Here are a few examples illustrating the key differences in your journal entries.

1) C Corp: Accruing and Paying Corporate Income Tax

A C corp is responsible for its own income tax. You'll accrue this liability and then pay it.

2025-03-31 * "Accrue federal corporate income tax for Q1"
Expenses:Taxes:Income 12500.00 USD
Liabilities:Taxes:Federal -12500.00 USD

2025-04-15 * "Pay Q1 2025 federal estimated tax"
Liabilities:Taxes:Federal 12500.00 USD
Assets:Bank:Checking -12500.00 USD

2) C Corp: Paying a Dividend vs. Retaining Earnings

When a C corp distributes profits, it's a dividend. This is a reduction of equity, not an expense.

2025-06-30 * "Board declares and pays cash dividend"
Equity:Dividends 50000.00 USD
Assets:Bank:Checking -50000.00 USD

If you retain the earnings instead, you simply don’t post this transaction. The profit stays in your Equity:RetainedEarnings account.

3) S Corp: Reasonable Salary & Payroll Taxes

S corp owners must be paid a salary. This is a standard payroll expense, complete with employer-side taxes.

2025-01-31 * "Owner payroll (gross wages and employer taxes)"
Expenses:Payroll:Wages 8000.00 USD ; Gross salary
Expenses:Payroll:EmployerFICA 612.00 USD ; Employer portion of taxes
Liabilities:Payroll:Federal -2000.00 USD ; Withholding + FICA
Liabilities:Payroll:State -400.00 USD ; State withholding
Assets:Bank:Checking -6212.00 USD ; Net pay to owner

2025-02-15 * "Remit payroll taxes to agencies"
Liabilities:Payroll:Federal 2000.00 USD
Liabilities:Payroll:State 400.00 USD
Assets:Bank:Checking -2400.00 USD

4) S Corp: Owner Distribution

This is how profits beyond salary are paid out in an S corp. Notice it is not an expense. It's a direct draw from equity, similar to a dividend, but with different tax implications for the owner.

2025-03-15 * "Owner distribution (profit pass-through)"
Equity:Distributions:OwnerA 20000.00 USD
Assets:Bank:Checking -20000.00 USD

The owner receives a Schedule K-1 detailing their share of the company's profit and handles the tax on their personal return.

Chart-of-Accounts Tips

  • Taxes:
    • C corp: You'll need Expenses:Taxes:Income and Liabilities:Taxes:Federal.
    • S corp: This income tax account is often unused at the federal level, but accounts for payroll taxes (Expenses:Payroll:Taxes and Liabilities:Payroll:*) are essential.
  • Equity:
    • C corp: A standard setup includes Equity:CommonStock, Equity:AdditionalPaidInCapital, Equity:RetainedEarnings, and Equity:Dividends.
    • S corp: Your chart will look similar but often uses Equity:Distributions instead of dividends. Some track Equity:AAA (Accumulated Adjustments Account) to manage distribution basis.
  • Payroll:
    • Both structures will need robust Expenses:Payroll:* and Liabilities:Payroll:* accounts if they have employees (including owner-employees).

Required IRS Forms (Common Cases)

  • C corp: Form 1120 (Annual Income Tax Return), Form 1120-W (Estimated Tax), Form 941 (Quarterly Payroll), Form 940 (Annual Unemployment/FUTA), Form 1099-DIV (for each shareholder receiving dividends), W-2/W-3.
  • S corp: Form 1120-S (Annual Income Tax Return), Schedule K-1 (for each shareholder), Form 941/940, W-2/W-3.
  • States: Remember that separate state income, franchise, and payroll tax returns will likely apply to both.

FAQ Quick Hits

  • Can an LLC be an S corp? Yes. An LLC can file Form 8832 to elect to be taxed as a corporation, and then file Form 2553 to elect S corp status (assuming it meets all eligibility rules).

  • Is an S corp “always cheaper” for taxes? Not necessarily. The benefit depends entirely on your profit levels, the owner's reasonable salary, state tax laws, and the individual owner's tax bracket.

  • Can S corps have preferred stock? No, not in an economic sense. S corps can only have one class of stock. You can have different voting rights (e.g., voting and non-voting common stock), but all shares must have identical rights to distributions and liquidation assets.

  • Can I switch from one to the other later? Yes, but it can be complex. Converting from a C corp to an S corp is common, but you must be mindful of timing and potential built-in gains (BIG) tax rules. Converting from an S corp to a C corp is also possible and often required before a VC funding round.


How Beancount.io Helps

No matter which entity you choose, Beancount.io provides the clarity and control you need.

  • Plain-text, version-controlled books that scale from a single-owner S corp to a venture-backed C corp.
  • Clear payroll and equity workflows that make it easy to distinguish distributions from dividends, track stock option expenses, and manage retained earnings.
  • Clean exports for your CPA, including a trial balance, income statement, and balance sheet, with a fully auditable trail for every number.
  • Powerful automations for bank feeds and document capture, without ever sacrificing the transparency of a human-readable ledger.

Want a head start? Ask for our sample C-corp and S-corp Beancount charts of accounts and example journal bundle.


*Disclaimer: This guide is for informational purposes only and does not constitute legal or tax advice. Tax laws and entity regulations vary by state and are subject to change. You should consult with a qualified CPA or attorney before choosing or changing your business entity type.*

S-Corp Election, Explained for Beancount Users

· 15 min read
Mike Thrift
Mike Thrift
Marketing Manager

What it is, when it pays off, and how to model it cleanly in your ledger (with examples).

⚠️ This guide is U.S.-specific and for education only. Talk to a tax pro for your situation.

TL;DR

  • An S-corp is a tax status you choose with the IRS (via Form 2553) so that business profits pass through to the owners' personal tax returns. A key requirement is that you must pay owner-operators a reasonable W-2 salary before taking any profit as dividends or distributions.
  • Deadlines matter: For an existing business, you must file no later than the 15th day of the 3rd month of the tax year you want the S-corp status to begin. For a calendar-year 2025 election, March 15, 2025, falls on a Saturday, so the practical deadline is the next business day, Monday, March 17, 2025.
  • Why do this? The main attraction is potential self-employment tax savings. While your W-2 salary is subject to FICA taxes, distributions are not. However, this benefit comes with added costs for payroll, compliance, and, in some states, extra entity-level taxes.
  • In Beancount, it's critical to separate wages from distributions. You'll need to track payroll liabilities, handle the special accounting for health insurance for shareholders owning more than 2% of the company, and record distributions explicitly through equity accounts.

2025-08-08-s-corp-election

What is an S-corp election?

At its core, an S-corp election is a request you make to the IRS to change how your business is taxed. By filing Form 2553, you ask the IRS to tax your corporation or LLC under Subchapter S of the Internal Revenue Code. This makes your business a "pass-through" entity, meaning its income, losses, deductions, and credits are passed directly to the shareholders' personal tax returns. It’s purely a tax classification, not a different type of legal business entity.

Key effects for an owner-operator

Once the election is active, your role fundamentally splits in two: you are now both a shareholder and an employee of your company.

This distinction is crucial. The compensation you receive for your labor must be paid as W-2 wages, which are subject to standard payroll taxes (Social Security and Medicare). Any remaining profit can then be paid out as distributions, which are generally not subject to self-employment taxes. The IRS insists that you pay yourself a reasonable salary for your work before you take any distributions.

Should you elect S-corp status?

The S-corp election is often worth evaluating once your business generates steady and meaningful profit. A common rule of thumb is to consider it when your ongoing business profit can comfortably support a market-rate salary for your role, with enough left over to make distributions worthwhile after covering all the new administrative costs.

The exact break-even point is unique to your situation and depends on several factors:

  • Your "Reasonable Salary": What would a business pay for someone with your skills and responsibilities in your industry? This figure is the baseline for your W-2 wages and is subject to IRS scrutiny.
  • State Taxes and Fees: Some states have their own rules. California, for example, imposes a 1.5% tax on an S-corp's net income, plus a minimum annual franchise tax of $800.
  • Added Costs: You'll need a payroll service, and you'll be paying for unemployment insurance. Your bookkeeping and tax preparation fees will also likely increase due to the added complexity.
  • QBI Deduction (Section 199A): The S-corp election can impact your Qualified Business Income deduction. The W-2 wages you pay yourself can either help you qualify for the full deduction or, at higher income levels, become a limiting factor.

Eligibility & Timing

Not every business can become an S-corp. Here are the high-level requirements:

  • It must be a domestic corporation or an eligible LLC.
  • It can have no more than 100 shareholders.
  • It can only have one class of stock.
  • Shareholders must be individuals, certain trusts, or estates (i.e., no partnerships, corporations, or non-resident alien shareholders).

When to file Form 2553

Timing is critical, and the rules differ slightly for new versus existing businesses.

  • For a new business: You must file within 2 months and 15 days after the first day of your first tax year. For example, if your business's tax year begins on January 7, your deadline is March 21.
  • For an existing C-corp (or an LLC taxed as a C-corp): You can file at any time during the preceding tax year or by the 15th day of the 3rd month of the year you want the election to take effect. If this date falls on a weekend or holiday, the deadline shifts to the next business day, a provision granted under IRC Section 7503.

What if you missed the deadline? Don't panic. The IRS provides a path for late-election relief under Revenue Procedure 2013-30. You can often file for this relief within 3 years and 75 days of the intended effective date, provided you have a reasonable cause for the late filing.

Reasonable Salary: The Part That Trips People Up

This is the most scrutinized aspect of the S-corp structure. The IRS is very clear: shareholder-employees must be paid reasonable compensation for the services they provide before any profits are taken as distributions.

What does "reasonable" mean? There's no single dollar amount. The IRS and courts look at a variety of factors to determine if your salary is appropriate, including your duties and responsibilities, the time you spend working, your level of experience, and what comparable businesses would pay for similar services. Expect the IRS to take a close look if you pay yourself a very low W-2 salary while taking large distributions. This is often seen as a red flag for attempting to evade payroll taxes.

Health Insurance & Fringe Benefits for >2% Shareholders

There's a special rule for how S-corps handle health insurance for shareholders who own more than 2% of the company. If the S-corp pays or reimburses these health insurance premiums, the cost is deductible by the S-corp.

However, the value of those premiums must also be included in the shareholder-employee's W-2 wages. While this amount is subject to federal income tax withholding, it is exempt from Social Security and Medicare (FICA) taxes as long as it's handled correctly. You must coordinate with your payroll provider to ensure these amounts are reported properly on your W-2.

State-Level Gotchas (Examples)

Federal S-corp status doesn't always translate directly at the state level. Always check your state's specific rules.

  • California: S-corps are subject to a 1.5% tax on their California-source net income. Additionally, most corporations must pay an $800 minimum franchise tax each year (though some exceptions apply for the first year).
  • New York: Making a federal S-corp election is not enough. You must also file a separate state-level election, Form CT-6, to be treated as a New York S-corporation. Failure to do so means you'll be taxed as a standard C-corp at the state level.

How to Model an S-corp Cleanly in Beancount

Plain text accounting is perfect for managing the added complexity of an S-corp. Here’s how to structure your ledger.

Suggested Chart of Accounts (Starter)

This basic structure separates your payroll expenses from distributions and creates liability accounts to track taxes you owe.

; Core bank & income
1970-01-01 open Assets:Bank:Checking USD
1970-01-01 open Income:Sales USD
1970-01-01 open Income:Other USD

; Payroll expenses & liabilities
1970-01-01 open Expenses:Payroll:Wages USD
1970-01-01 open Expenses:Payroll:EmployerTaxes USD
1970-01-01 open Expenses:Benefits:HealthInsurance USD
1970-01-01 open Liabilities:Payroll:Federal:FIT USD
1970-01-01 open Liabilities:Payroll:FICA USD
1970-01-01 open Liabilities:Payroll:Medicare USD
1970-01-01 open Liabilities:Payroll:State:Withholding USD

; Equity
1970-01-01 open Equity:ContributedCapital USD
1970-01-01 open Equity:Distributions USD
1970-01-01 open Equity:RetainedEarnings USD

Typical Payroll Run (Simplified)

Your payroll provider (e.g., Gusto, ADP) will debit your bank account for your net pay and the total tax liability. Your Beancount transaction should break this down into the gross wages, employer taxes, and the corresponding liabilities.

; This transaction records a $100k annual salary, paid monthly.
2025-01-31 * "Gusto" "Jan payroll — shareholder-employee"
Expenses:Payroll:Wages 8,333.33 USD ; Gross wages
Expenses:Payroll:EmployerTaxes 637.50 USD ; Employer-side FICA/Medicare
Liabilities:Payroll:Federal:FIT -1,200.00 USD ; Employee withholding
Liabilities:Payroll:FICA -516.67 USD ; Employee withholding
Liabilities:Payroll:Medicare -120.83 USD ; Employee withholding
Assets:Bank:Checking -7,133.33 USD ; Net pay debited from bank

When your payroll provider remits those taxes to the government on your behalf, you'll record another transaction to clear out the liabilities.

; This represents the tax payment made by your payroll provider.
2025-02-15 * "EFTPS" "Federal payroll tax deposit"
Liabilities:Payroll:Federal:FIT 1,200.00 USD
Liabilities:Payroll:FICA 516.67 USD
Liabilities:Payroll:Medicare 120.83 USD
Assets:Bank:Checking -1,837.50 USD ; This amount matches the tax portion of the Gusto debit.

Health Insurance for a >2% Shareholder

Record the premium payment as a business expense. You can use metadata to remind yourself that this needs to be reported on the W-2.

2025-02-01 * "BlueCross" "Shareholder health insurance (report on W-2)"
Expenses:Benefits:HealthInsurance 600.00 USD ; w2: "true"
Assets:Bank:Checking -600.00 USD

Owner Distributions (Not Wages)

Distributions are a reduction of equity, not a business expense. Record them separately from payroll.

2025-03-31 * "Owner Distribution" "Q1 distribution"
Equity:Distributions 20,000.00 USD
Assets:Bank:Checking -20,000.00 USD

Your shareholder basis determines whether distributions are tax-free and whether you can deduct business losses on your personal return. While the official calculation is done on your tax return, you can track an estimate in Beancount using a dedicated equity subaccount or metadata. You'll reconcile this to the Schedule K-1 you receive from the S-corp annually.

A Note on the QBI Deduction (Section 199A)

Owners of pass-through businesses, including S-corps, may be eligible for up to a 20% deduction on their qualified business income (QBI). However, for taxpayers with income above a certain threshold, this deduction can be limited by the amount of W-2 wages the business pays. This creates a complex interplay: paying a reasonable salary is required for an S-corp, and those same wages can impact your QBI deduction—sometimes helping it, sometimes limiting it. This is a key area to model with your tax professional.

What Changes Operationally After You Elect?

Switching to an S-corp adds a few administrative layers:

  • Run Payroll: You must formally run payroll, complete with tax withholdings, employer tax payments, quarterly filings, and year-end W-2s.
  • File Form 1120-S: This is the annual S-corporation tax return. You'll also issue a Schedule K-1 to each shareholder detailing their share of the company's financial results.
  • Handle Shareholder Health Insurance Correctly: Ensure premiums for >2% owners are included in their W-2 wages.
  • Mind State Rules: Stay on top of any required state-level S-corp elections or entity taxes (like in CA and NY).

Common Pitfalls to Avoid

  • Late or Invalid Election: Double-check deadlines and ensure all required shareholders sign Form 2553. If you miss it, investigate relief under Rev. Proc. 2013-30.
  • Unreasonable Salary: Don't be tempted to pay yourself an artificially low salary. Document why your compensation is reasonable based on your role and market data.
  • Mixing Wages and Distributions: Keep these transactions clean and separate in your books. Distributions are not payroll.
  • Ignoring State Requirements: Forgetting a state election or failing to pay an entity-level tax can lead to penalties and compliance headaches.

Quick Checklist

  • Confirm you are eligible and that the potential tax savings outweigh the new costs.
  • Calendar the Form 2553 filing deadline (and remember the weekend/holiday rule).
  • Set up a payroll service and determine a well-documented, reasonable salary.
  • Plan to take distributions only after salary and business expenses are paid.
  • Investigate and comply with your state's specific S-corp filing requirements and taxes.
  • Update your Beancount ledger with the necessary accounts for payroll, liabilities, and shareholder equity.

Beancount S‑Corp Starter (neutral template)

;
; Beancount S‑Corp Starter (neutral template)
; Generated: 2025-08-09
; ---
; How to use this:
; 1) Search for "TODO" and fill in your state(s), payroll provider, EIN, and bank names.
; 2) Keep wages and owner distributions separate.
; 3) Coordinate with your payroll provider to report >2% shareholder health insurance on the W‑2 (Box 1).
; 4) Delete or adapt the CA/NY examples if you’re in a different state.
;
; Notes:
; - This is a bookkeeping template, not tax advice.
; - Operating currency assumed USD. Change as needed.
;

option "title" "S‑Corp Ledger"
option "operating_currency" "USD"
commodity USD

; === Accounts (open as of 2025-01-01; adjust dates as needed) ==================
2025-01-01 open Assets:Bank:Checking USD ; TODO: Rename to your bank (e.g., Assets:Bank:Chase:Operating)
2025-01-01 open Assets:Bank:Savings USD
2025-01-01 open Assets:AccountsReceivable USD
2025-01-01 open Assets:PrepaidExpenses USD

2025-01-01 open Liabilities:CreditCard:Corporate USD
2025-01-01 open Liabilities:Payroll:Federal:FIT USD
2025-01-01 open Liabilities:Payroll:Federal:FICA USD
2025-01-01 open Liabilities:Payroll:Federal:Medicare USD
2025-01-01 open Liabilities:Payroll:Federal:FUTA USD
2025-01-01 open Liabilities:Payroll:State:Withholding USD ; TODO: Rename state (e.g., CA, NY)
2025-01-01 open Liabilities:Payroll:State:Unemployment USD
2025-01-01 open Liabilities:Payroll:Local USD

2025-01-01 open Equity:ContributedCapital USD
2025-01-01 open Equity:Distributions USD
2025-01-01 open Equity:RetainedEarnings USD
2025-01-01 open Equity:OpeningBalances USD

2025-01-01 open Income:Sales USD
2025-01-01 open Income:Other USD

2025-01-01 open Expenses:COGS USD
2025-01-01 open Expenses:Payroll:Wages USD
2025-01-01 open Expenses:Payroll:EmployerTaxes:FICA USD
2025-01-01 open Expenses:Payroll:EmployerTaxes:Medicare USD
2025-01-01 open Expenses:Payroll:EmployerTaxes:FUTA USD
2025-01-01 open Expenses:Payroll:EmployerTaxes:State USD
2025-01-01 open Expenses:Benefits:HealthInsurance USD
2025-01-01 open Expenses:Benefits:HSA USD
2025-01-01 open Expenses:Benefits:Retirement:Match USD
2025-01-01 open Expenses:Taxes:State:S‑Corp USD ; e.g., CA 1.5% entity‑level tax
2025-01-01 open Expenses:Taxes:State:Franchise USD ; e.g., CA $800 minimum franchise tax
2025-01-01 open Expenses:Professional:Payroll USD
2025-01-01 open Expenses:Professional:Accounting USD
2025-01-01 open Expenses:Professional:Legal USD
2025-01-01 open Expenses:BankFees USD
2025-01-01 open Expenses:Software USD
2025-01-01 open Expenses:Office USD
2025-01-01 open Expenses:Meals USD
2025-01-01 open Expenses:Travel USD
2025-01-01 open Expenses:Insurance:GeneralLiability USD

; === Example: Owner capitalization =================================================
2025-01-02 * "Owner" "Initial capital contribution"
Assets:Bank:Checking 25,000.00 USD
Equity:ContributedCapital -25,000.00 USD

; === Example: Customer payment =====================================================
2025-01-15 * "Stripe" "January subscription receipts"
Assets:Bank:Checking 12,000.00 USD
Income:Sales -12,000.00 USD

; === Example: Monthly payroll (single shareholder‑employee) ========================
; Numbers chosen to balance perfectly. Adapt FIT/State numbers to your reality.
; Gross wages: 8,333.33 | Employee FIT: 1,200.00 | State Withholding: 300.00
; Employee FICA (6.2%): 516.67 | Employee Medicare (1.45%): 120.83
; Employer FICA: 516.67 | Employer Medicare: 120.83
; Net pay: 6,195.83
2025-01-31 * "Gusto" "Jan payroll — shareholder‑employee"
Expenses:Payroll:Wages 8,333.33 USD
Expenses:Payroll:EmployerTaxes:FICA 516.67 USD
Expenses:Payroll:EmployerTaxes:Medicare 120.83 USD
Liabilities:Payroll:Federal:FIT -1,200.00 USD
Liabilities:Payroll:Federal:FICA -1,033.34 USD ; employee + employer
Liabilities:Payroll:Federal:Medicare -241.66 USD ; employee + employer
Liabilities:Payroll:State:Withholding -300.00 USD
Assets:Bank:Checking -6,195.83 USD

; === Example: Payroll tax deposits (EFTPS & State) =================================
2025-02-15 * "EFTPS" "Federal payroll deposit (FIT, FICA, Medicare)"
Liabilities:Payroll:Federal:FIT 1,200.00 USD
Liabilities:Payroll:Federal:FICA 1,033.34 USD
Liabilities:Payroll:Federal:Medicare 241.66 USD
Assets:Bank:Checking -2,475.00 USD

2025-02-16 * "STATE DOR" "State payroll withholding"
Liabilities:Payroll:State:Withholding 300.00 USD
Assets:Bank:Checking -300.00 USD

; === Example: Health insurance for >2% shareholder =================================
; Coordinate with payroll so the annual premium total is included in W‑2 Box 1.
; The premium itself is deductible here; do NOT withhold SS/Medicare on it when handled properly.
2025-02-01 * "BlueCross" "Shareholder health insurance (W‑2 inclusion handled by payroll)"
Expenses:Benefits:HealthInsurance 600.00 USD ; w2: "true"
Assets:Bank:Checking -600.00 USD

; === Example: Owner distribution (not wages) =======================================
2025-03-31 * "Owner Distribution" "Q1 distribution"
Equity:Distributions 20,000.00 USD
Assets:Bank:Checking -20,000.00 USD

; === State examples (delete/edit if not applicable) =================================
; California minimum franchise tax (not always first year; check rules)
2025-04-15 * "California FTB" "Annual franchise tax"
Expenses:Taxes:State:Franchise 800.00 USD
Assets:Bank:Checking -800.00 USD

; California S‑Corp 1.5% entity‑level tax (example estimate payment)
2025-06-15 * "California FTB" "S‑Corp tax estimate"
Expenses:Taxes:State:S‑Corp 1,500.00 USD
Assets:Bank:Checking -1,500.00 USD

; New York separate S election (CT‑6) has no direct ledger impact; placeholder note.
2025-01-05 note Equity:RetainedEarnings "NY S‑election (CT‑6) filed — bookkeeping note only (no entry)"

; === Basis tracking (optional — off‑book memo) =====================================
2025-12-31 note Equity:RetainedEarnings "Basis rollforward: +Capital 25,000 +Income 60,000 −Distributions 20,000 = End basis 65,000 (reconcile to K‑1)"

; === Import hints (CSV from Gusto/ADP) =============================================
; - For Gusto payroll register CSVs, map columns:
; Gross Pay -> Expenses:Payroll:Wages
; Employee FIT/FICA/Medicare -> Liabilities:Payroll:Federal:FIT/FICA/Medicare (negative)
; State Withholding -> Liabilities:Payroll:State:Withholding (negative)
; Employer FICA/Medicare/FUTA/SUTA -> Expenses:Payroll:EmployerTaxes:* (positive) AND
; if your CSV lists employer taxes as amounts owed, mirror them as Liabilities:* (negative),
; then clear with your EFTPS/state payments.
; Net Pay -> Assets:Bank:Checking (negative, matches pay date)
; - Health insurance paid by company:
; Vendor payment -> Expenses:Benefits:HealthInsurance (positive) / Bank (negative);
; ensure payroll includes the annual premium in W‑2 Box 1 for >2% shareholder.
;
; Tips:
; - Keep distributions out of payroll accounts.
; - Use tags like #payroll #distribution to filter in Fava.
; - Consider separate bank subaccounts for tax set‑asides (federal/state).

S Corp vs. LLC: What’s the Difference—and Which Fits Your Books?

· 10 min read
Mike Thrift
Mike Thrift
Marketing Manager

Choosing a business structure is one of the first real “finance” decisions you’ll make. For most small teams and solo founders who want liability protection and pass-through taxation, the short list is usually an LLC or an S corporation.

This guide explains how they differ—legally, operationally, and on your tax return—and shows how to keep clean, audit-proof records for either structure in Beancount.io (plain-text, double-entry accounting that scales from freelancer to S corp).

2025-08-11-s-corp-vs-llc


At a Glance

S CorpLLC
What it isA tax status you elect with the IRS for a corporation or LLCA state-created legal entity with flexible governance
Liability shieldYesYes
OwnersUp to 100 U.S. shareholders; no entity ownersUnlimited members; entities and non-U.S. owners allowed (varies by state)
OperationsCorporate bylaws, directors/officers, meetings and minutesGoverned by operating agreement; fewer formalities
Classes of equityOne class of stock (economic rights must be identical)Flexible membership units and waterfalls
TaxationPass-through; files Form 1120-SDefault pass-through (Schedule C or Form 1065); can elect S or C taxation
Owner payOwners who work must take reasonable salary via payrollMembers take distributions; no payroll required for owners by default
Lifespan & transferPerpetual; shares generally transferableOften needs member consent to transfer; rules set in operating agreement
Fits best whenProfitable, owner-operators on payroll; cleaner investor signalingFlexible ownership, profit splits, or non-U.S./entity members; simpler operations

How They Actually Differ

While both LLCs and S corps offer a crucial liability shield, their legal and financial mechanics are fundamentally different. Here’s a deeper look at what sets them apart.

Formation and Formalities

A Limited Liability Company (LLC) is a legal entity created by state law. The process involves filing "articles of organization" with your state and adopting an "operating agreement," which is a flexible internal document that outlines how the business will be run and how profits will be split.

An S corporation, on the other hand, is not a legal entity itself but a tax election made with the IRS by filing Form 2553. This election can be applied to either a standard C corporation or an LLC. Once you elect S corp status, you must adhere to stricter corporate formalities, including drafting bylaws, appointing a board of directors and officers, holding annual meetings, and keeping detailed records of those meetings (known as "minutes").

Ownership & Investors

Ownership flexibility is a hallmark of the LLC. You can have an unlimited number of owners (called "members"), including individuals, other corporations, and foreign citizens. The operating agreement allows for custom profit splits ("waterfalls") and different classes of membership, which is ideal for complex partnerships.

The S corp is far more restrictive. It can have no more than 100 owners (called "shareholders"), all of whom must be U.S. citizens or residents. Other entities (like corporations or partnerships) cannot be shareholders. Furthermore, S corps can only have one class of stock, meaning all shareholders have identical economic rights (profits and distributions must be allocated proportionally to ownership). This simplicity can make the cap table cleaner but severely limits who can invest.

Taxes & Filings

By default, an LLC is a pass-through entity.

  • A single-member LLC is a "disregarded entity," meaning its income and expenses are reported on a Schedule C filed with the owner’s personal Form 1040.
  • A multi-member LLC files a partnership tax return, Form 1065, and issues a Schedule K-1 to each member detailing their share of the profit or loss.

An S corp is also a pass-through entity, but it files its own business tax return, Form 1120-S, and also issues K-1s to its shareholders. The key difference is that any owner who works for the company must be treated as an employee and paid a reasonable salary through a formal payroll system.

How Owners Get Paid

This is one of the most significant distinctions. LLC members are not employees. They get paid by taking distributions (or "draws") of the company's profits. Members are responsible for paying their own income and self-employment taxes (Social Security and Medicare) on their entire share of the net profits, regardless of how much cash they actually took out.

S corp owner-employees face a two-part system.

  1. Reasonable Salary: They must be paid a reasonable wage for the work they perform, which is subject to standard payroll taxes (FICA). The company pays the employer portion, and the employee pays their portion.
  2. Distributions: Any remaining profits can be paid out as distributions, which are not subject to self-employment or FICA taxes. This potential tax saving is the primary reason businesses elect S corp status. The IRS requires the salary to be "reasonable," so you can't pay yourself $1 and take the rest in distributions; you must document how you determined the salary amount.

Transferability & Lifespan

S corp stock functions like typical corporate shares. It is generally freely transferable (unless restricted by a shareholder agreement), and the corporation has a perpetual existence, meaning it continues even if a shareholder leaves or passes away.

Transferring ownership in an LLC is often more complex. The operating agreement dictates the rules, and it typically requires the consent of the other members to sell or transfer ownership units. This protects members from being forced into business with strangers but can make exiting the business more cumbersome.


Should You Elect S Corp Status for Your LLC?

A very common path for successful small businesses is to start as an LLC and elect S corp taxation later. This "LLC now, S corp when profitable" strategy allows you to enjoy the simplicity of an LLC in the early stages and switch for tax optimization once your income grows.

Founders typically make the switch when:

  • Profits are steady and significant. The amount paid in self-employment tax as an LLC member becomes greater than the FICA taxes on a reasonable salary plus the compliance costs of an S corp.
  • They desire more structure. The formal requirements of an S corp can enforce better financial discipline and send a more "serious" signal to lenders or future investors.

Electing S corp status for your LLC brings concrete changes:

  • You must set up and run payroll for all owner-employees.
  • You must adhere to corporate record-keeping, including holding meetings and documenting them with minutes.
  • Your annual tax preparation becomes more complex, requiring Form 1120-S and K-1s.

When is it better to remain an LLC?

  • You need flexible ownership structures, like special profit allocations or having a corporation or foreign partner as a member.
  • Your profit is volatile or you are still in the early stages. The overhead and cost of running payroll might not be worth it yet.
  • You plan to issue complex equity, like token-based compensation or preferred units, that don't fit the S corp's "one class of stock" rule.

Practical Rule of Thumb: Before you switch, model your next 12 months of expected profit. Calculate your total tax burden (income + self-employment tax) as an LLC. Then, calculate your total tax burden as an S corp (income tax + FICA tax on a reasonable salary). If the savings from the S corp structure are clear, recurring, and outweigh the added compliance costs, the election is worth a serious look. Be sure to document your analysis for determining a "reasonable salary."


How to Keep Either Structure Clean in Beancount.io

No matter which entity you choose, chaotic books can undermine your liability protection and create tax-time nightmares. Beancount.io gives you a plain-text, double-entry ledger with automated imports and tax-ready reports, so your legal structure doesn’t turn into bookkeeping sprawl.

Chart of Accounts Suggestions

A clean chart of accounts is the foundation. Here are our recommendations:

  • For an LLC:
    • Equity:Member-Capital (for initial and subsequent contributions)
    • Equity:Member-Distributions (for owner draws)
    • Standard Income and Expense accounts.
  • For an S corp:
    • Equity:Common-Stock (for capital contributions)
    • Equity:Retained-Earnings (where profits accumulate)
    • Expenses:Payroll:Wages
    • Expenses:Payroll:EmployerTaxes
    • Equity:Shareholder-Distributions (for payments out of profit)

Example Entries

Here’s how common owner payments look in a Beancount.io ledger.

LLC member distribution: This transaction records a $5,000 payment to a member, reducing cash and tracking the draw in a dedicated equity account.

2025-03-15 * "Member distribution"
Assets:Bank:Checking -5,000 USD
Equity:Member-Distributions 5,000 USD

S corp owner salary (from a payroll run): This entry captures the gross wage, the employer's share of payroll taxes, and the total cash leaving the bank. Withholding liabilities would also be tracked here.

2025-03-31 * "Owner payroll"
Expenses:Payroll:Wages 8,000 USD
Expenses:Payroll:EmployerTaxes 612 USD
Assets:Bank:Checking -8,612 USD
Liabilities:Payroll:Withholding 0 USD ; Net pay + withholdings

S corp shareholder distribution: This is a simple transfer from cash to the shareholder distribution equity account, separate from payroll.

2025-04-10 * "Shareholder distribution"
Assets:Bank:Checking -10,000 USD
Equity:Shareholder-Distributions 10,000 USD

Close the Loop at Tax Time

With a clean Beancount.io ledger, tax season is streamlined:

  • Generate your Profit & Loss and Balance Sheet statements directly from your transactions.
  • Export the data your accountant needs for your specific tax form (Schedule C, 1065, or 1120-S).
  • Keep your reasonable salary memos, meeting minutes, and other compliance documents alongside your transactions for a complete, audit-ready financial record.

When Each Choice Shines

Here's the decision in a nutshell.

Choose (or remain) an LLC if you want:

  • Maximum flexibility in ownership, profit splits, or bringing in entity/foreign members.
  • Minimal corporate formalities and no mandatory owner payroll.
  • Simpler compliance while you are finding product-market fit or have inconsistent profits.

Choose (or elect) an S corp if you want:

  • Potential savings on self-employment (FICA) taxes once your profits can justify a formal payroll.
  • A clean, traditional corporate structure with straightforward stock transferability.
  • A governance model that investors and lenders often prefer for established operating companies.

Bottom Line

Both LLCs and S corps protect your personal assets and allow business profits to pass through to the owners for tax purposes. The best fit depends entirely on your ownership structure, your expected profitability, and your appetite for formal governance and payroll.

Whichever you choose, disciplined bookkeeping matters far more than the entity's label. Keep your financial records precise, searchable, and reproducible with Beancount.io.


Build Tax-Ready, Investor-Ready Books with Beancount.io

  • Plain-text, version-controlled double-entry accounting.
  • Clean charts of accounts designed for LLCs and S corps.
  • Automated bank, credit card, and processor imports and reconciliations.
  • Tax-ready exports and seamless accountant collaboration.
  • A system that scales from a solo founder to a multi-entity enterprise.

Start a streamlined ledger for your entity today with Beancount.io.


This guide is for informational purposes and is not legal or tax advice. Consult your attorney or tax advisor for guidance specific to your situation.

S Corp Stock Basis—A Practical Guide for Founders (with Beancount.io examples)

· 8 min read
Mike Thrift
Mike Thrift
Marketing Manager

If you run an S corporation, shareholder basis is the quiet number that decides whether your losses are deductible and whether distributions are tax-free. It changes every year, and it’s your responsibility (as a shareholder) to track it. Here’s the plain-English version—plus how to model basis cleanly in Beancount.io.


2025-08-06-s-corp-stock-basis-a-practical-guide-for-founders

What “Basis” Means (Fast)

Think of your stock basis as your personal investment scorecard in the S corporation. It starts with your initial contribution—what you paid for your shares or the value of property you put into the company. From there, it's a dynamic figure.

Your basis increases when the company makes money (your share of its income, even tax-exempt income) or when you contribute more capital. It decreases when you take tax-free distributions, or when the company has losses, deductions, or nondeductible expenses.

Crucially, your stock basis can never drop below zero. If the company’s losses are greater than your basis, the excess losses become suspended. You can't deduct them now, but you can carry them forward to use in a future year when you have enough basis. You'll use Form 7203, filed with your personal Form 1040, to report your basis calculation and track any suspended losses.

If you've also made a direct loan to your S corp, you might have debt basis, which provides a second layer to absorb losses after your stock basis is wiped out.


S Corp vs. C Corp Basis (TL;DR)

The concept of basis is completely different between S and C corporations.

  • S corp basis is fluid and must be adjusted annually. It directly reflects the company's performance because of its pass-through nature. Profits and losses flow through to you and directly impact your basis.
  • C corp stock basis is generally static. It’s simply what you paid for the stock. It only changes due to specific corporate actions like stock splits or a formal return of capital, not because the company had a profitable or unprofitable year.

How to Compute S Corp Basis (The Correct Order)

Calculating your basis isn't just about adding and subtracting; it’s about doing it in the right sequence. The IRS mandates a specific order of operations. Each year, you’ll take your Schedule K-1 (from the S corp's Form 1120-S) and adjust your basis from the beginning of the year as follows:

  1. Increase for all income items, including both taxable income and tax-exempt income (like municipal bond interest).
  2. Decrease for distributions you received during the year (but not below zero).
  3. Decrease for nondeductible expenses (like certain penalties or entertainment expenses).
  4. Decrease for losses and deductions (like ordinary business loss or charitable contributions).

If the total losses and deductions in Step 4 exceed your remaining basis, you must prorate them. The excess is suspended and carried forward until you restore your basis through future income or capital contributions.

Important Notes:

  • Personally guaranteeing a company loan does not create basis. You only get basis when you actually pay on that guarantee out of your own pocket.
  • Owner wages (your salary from the S corp) do not affect your basis. This is compensation for your labor and is treated as a business expense for the company and W-2 income for you, completely separate from your role as an owner.

Worked Example (Numbers That Reconcile)

Let's walk through an example to see the ordering rules in action.

Facts for a single shareholder for the year:

  • Initial capital contribution: $18,000
  • Ordinary dividends (K-1 Box 5a): $2,000
  • Distributions received (K-1 Box 16D): $7,000
  • Share of nondeductible expenses (K-1 Box 16C): $3,000
  • Share of ordinary business loss (K-1 Box 1): ($9,000)
  • Share of charitable contribution (K-1 Box 12A): $6,000
  • The shareholder has no debt basis.

Here is the step-by-step calculation:

Step 1 — Increase for income Your starting basis of 18,000increasesbythe18,000 increases by the 2,000 of dividend income. 18,000+18,000 + 2,000 = $20,000

Step 2 — Decrease for distributions Next, reduce the basis by the cash distributions you took. 20,00020,000 − 7,000 = $13,000

Step 3 — Decrease for nondeductible expenses Now, subtract the nondeductible expenses. Your basis before applying losses is 10,000.10,000. 13,000 − 3,000=3,000 = **10,000**

Step 4 — Apply losses and deductions Your total losses and deductions are 15,000(15,000 (9,000 ordinary loss + 6,000charitable).Sincethisexceedsyourremainingbasisof6,000 charitable). Since this exceeds your remaining basis of 10,000, you can only deduct a proportional amount.

  • Allowable ordinary loss = (9,000÷9,000 ÷ 15,000) × 10,000=10,000 = **6,000**
  • Allowable charitable contribution = (6,000÷6,000 ÷ 15,000) × 10,000=10,000 = **4,000**

The remaining amounts are suspended and carried forward to next year: a 3,000ordinarylossanda3,000 ordinary loss and a 2,000 charitable contribution.

Your ending stock basis for the year is $0, as it can’t go negative. You'll report the allowed loss and deduction on your tax return and track the suspended amounts for future use.


Tracking S Corp Basis in Beancount.io (Plain-Text Pattern)

Instead of a messy spreadsheet, you can maintain a simple, auditable basis ledger directly in Beancount.io. This can live in your corporate books or a personal mirror file. The key is to use a "memo" equity account to track the running basis calculation.

Suggested Accounts:

  • Equity:Shareholder:Paid-In-Capital
  • Equity:Shareholder:Distributions
  • Equity:Shareholder:Stock-Basis (This is your off-balance-sheet "memo" account that tracks the official running basis for Form 7203.)
  • Income:PassThrough:*
  • Expenses:Nondeductible
  • Expenses:Charitable

Example Entries:

Initial Capital Contribution: This entry records the cash coming into the company and simultaneously sets the initial stock basis in your memo account.

2025-01-10 * "Initial capital"
Assets:Bank:Operating -18,000 USD
Equity:Shareholder:Paid-In-Capital 18,000 USD
Equity:Shareholder:Stock-Basis 18,000 USD

K-1 Ordinary Dividends: Record the pass-through income and the corresponding increase to your basis.

2025-12-31 * "K-1 Box 5a ordinary dividends"
Income:PassThrough:Dividends -2,000 USD
Equity:Shareholder:Stock-Basis 2,000 USD

Distribution to Shareholder: This captures the cash leaving the company and the corresponding reduction in your basis.

2025-07-15 * "Shareholder distribution"
Equity:Shareholder:Distributions 7,000 USD
Assets:Bank:Operating -7,000 USD
Equity:Shareholder:Stock-Basis -7,000 USD

Nondeductible Expenses: Log the expense and the basis reduction.

2025-12-31 * "K-1 Box 16C nondeductible"
Expenses:Nondeductible 3,000 USD
Assets:Bank:Operating -3,000 USD
Equity:Shareholder:Stock-Basis -3,000 USD

Allowable Losses/Deductions: Record only the portion of losses allowed this year, reducing your basis to zero. Use a comment to track suspended items.

2025-12-31 * "K-1 losses allowed this year (Box 1 + Box 12A, limited by basis)"
Income:PassThrough:Ordinary-Loss 6,000 USD
Expenses:Charitable 4,000 USD
Equity:Shareholder:Stock-Basis -10,000 USD
; Suspended to next year: 3,000 ordinary loss, 2,000 charitable

This pattern keeps a transparent running basis in the Equity:Shareholder:Stock-Basis account that ties exactly to your Form 7203. Auditors love it because every change is a dated, traceable transaction.


Common Pitfalls

Avoid these frequent mistakes when managing your S corp basis:

  • Treating guarantees as basis. A loan guarantee is just a promise. It doesn't become basis until you actually use your personal funds to pay down the corporate debt.
  • Taking distributions with insufficient basis. If you take a distribution that exceeds your basis, the excess amount is not tax-free. It's typically taxed as a capital gain.
  • Forgetting to include tax-exempt income. Tax-exempt income (like life insurance proceeds or certain interest) still increases your basis, which can create more room to deduct losses.
  • Mixing up owner wages and distributions. Your salary is an expense to the business and taxable compensation to you. It does not affect basis. Distributions are returns of capital/profit and directly reduce basis.

Bottom Line

Your S corp basis is the throttle on your loss deductions and the shield for your tax-free distributions. It is essential to track it methodically, follow the official ordering rules, and attach a complete Form 7203 to your tax return each year. Whether you started as an S corp or are an LLC taxed as one, clean, disciplined books make basis calculations straightforward and defensible.


Keep Basis (and Everything Else) Tidy with Beancount.io

  • Plain-text, double-entry ledgers that are version-controlled and auditable.
  • K-1-friendly categories and dedicated memo accounts for basis tracking.
  • Automated imports from banks, credit cards, and processors to reduce manual entry.
  • Tax-ready reports that your preparer can use directly.

Start a clean, auditable S-corp workflow with Beancount.io today.

This article is for informational purposes only and is not tax or legal advice. Consult your advisor for guidance specific to your situation.

Beyond Pass-Through: The Complete S-Corp Tax Guide for Beancount Users (2025)

· 7 min read
Mike Thrift
Mike Thrift
Marketing Manager

You formed an S-corp to keep your business lean and tax-efficient. But while the "pass-through" concept sounds simple, the reality involves payroll taxes, potential entity-level charges, and crucial state-by-state differences.

Here’s how the taxes actually work for an S-corp in 2025—and how to keep a clean, audit-proof record in Beancount.

2025-07-26-s-corp-tax-guide-for-beancount-users


What Gets Taxed (and Where)

The core of the S-corp structure is how it handles profit. It's a three-part system: pass-through income, entity-level taxes, and payroll taxes.

  • Pass-Through at the Federal Level: An S-corp generally pays no federal income tax on its ordinary business profit. Instead, that profit (along with other tax items like credits and deductions) flows through to the shareholders via a Schedule K-1. Shareholders report this income on their personal tax returns, whether or not they actually took the cash out of the business. Crucially, this K-1 profit is not subject to self-employment tax.
  • But... Entity-Level Taxes Can Apply: The "no corporate tax" rule isn't absolute. In specific cases, an S-corp may owe tax directly. The most common triggers are the built-in gains (BIG) tax (for recent C-corp conversions) and the excess net passive income tax.
  • Payroll Taxes Are Real: This is the most important rule for shareholder-employees. If you work in your business, you must be paid reasonable compensation as W-2 wages before you take any tax-favored distributions. These wages are subject to FICA (Social Security & Medicare) and income tax withholding, just like any other employee's pay.

Payroll, at a Glance (2025) payroll

For any shareholder-employee, you'll be running payroll and filing standard payroll tax forms, including quarterly Form 941 (for income tax withholding and FICA) and annual Form 940 (for federal unemployment tax, or FUTA).

The key 2025 rates are:

  • Social Security (OASDI): The wage base is $176,100. The tax rate is 6.2% for the employee and 6.2% for the employer on wages up to this cap.
  • Medicare: There is no wage cap. The rate is 1.45% for the employee and 1.45% for the employer on all wages.
  • Additional Medicare Tax: A 0.9% tax is withheld from an employee's wages that exceed $200,000 in a year. There is no employer match for this portion.

Entity-Level Taxes You Might See

While less common, you must be aware of taxes the S-corp itself might owe.

  • Built-in Gains (BIG) Tax: If you converted your business from a C-corp to an S-corp, you face a 5-year recognition period. If you sell appreciated assets that the company held during its C-corp days within this window, the S-corp itself will owe a corporate-rate tax on those gains. This is calculated on Schedule D of Form 1120-S.
  • Excess Net Passive Income Tax: This applies if your S-corp has accumulated earnings & profits (AE&P) from a prior life as a C-corp and its passive income (like rents, royalties, and interest) exceeds 25% of its gross receipts.
  • Quarterly Estimates for These Taxes: If you expect the total of BIG tax, passive income tax, and certain other recapture taxes to be $500 or more, the S-corp must make quarterly estimated payments. For 2025, the calendar-year due dates are April 15, June 16, September 15, and December 15.

State & Local Gotchas 🗺️

Never assume federal rules apply at the state or city level. Tax treatment varies widely.

  • California: S-corps must pay an $800 minimum franchise tax each year, plus a 1.5% tax on net income.
  • New York City: NYC does not recognize the S-corp election. A federal S-corp is generally subject to the full NYC General Corporation Tax.
  • Elective Pass-Through Entity (PTE) Taxes: As a workaround to the federal $10,000 SALT deduction cap, many states now allow S-corps to elect to pay state income tax at the entity level. The rules are complex and shifting—talk to your CPA before making a PTE election.

What the Owners Pay

As a shareholder, your personal tax picture is directly linked to the S-corp's performance.

  • K-1 Income on Your 1040: You will report the income, losses, deductions, and credits passed through to you on your Schedule K-1 on your personal Form 1040.
  • Quarterly Estimated Taxes: Since your K-1 income doesn't have taxes withheld, you will likely need to make personal quarterly estimated tax payments to the IRS using Form 1040-ES to avoid underpayment penalties.
  • The QBI Deduction (Section 199A): Your pass-through income may qualify for the valuable Qualified Business Income (QBI) deduction, which can be up to 20% of your business income. At higher income levels, this deduction can be limited by the amount of W-2 wages the S-corp pays—making your "reasonable compensation" figure even more important.

Baseline Filing & Forms

At a minimum, your annual compliance will include:

  • Form 1120-S: The S-corporation income tax return.
  • Schedule K-1: For each shareholder.
  • Payroll Forms: Quarterly 941s, annual 940, and W-2s/W-3s for employees.
  • Form 1099-NEC: For payments of $600 or more to most independent contractors.

Beancount: Map It So You Never Wonder “Where Did That Go?”

A clear chart of accounts is essential for tracking these moving parts.

Starter Accounts

Assets:Bank:Operating
Assets:PrepaidTax:Federal ; For S-corp level estimated payments
Expenses:Payroll:Wages
Expenses:Payroll:Employer:SocialSecurity
Expenses:Payroll:Employer:Medicare
Expenses:Payroll:Employer:FUTA
Expenses:Tax:Federal:S-Corp ; For BIG/passive income tax expense
Liabilities:Payroll:Withholding:{Federal,SocialSecurity,Medicare}
Equity:Distributions

Transaction Examples

Run Payroll (Company side + withholdings)

2025-02-28 * "Payroll - February"
Assets:Bank:Operating -10350.00 USD
Expenses:Payroll:Wages 12500.00 USD
Expenses:Payroll:Employer:SocialSecurity 775.00 USD
Expenses:Payroll:Employer:Medicare 181.25 USD
Liabilities:Payroll:Withholding:Federal -3000.00 USD
Liabilities:Payroll:Withholding:SocialSecurity -775.00 USD
Liabilities:Payroll:Withholding:Medicare -181.25 USD

Owner Distribution (Non-wage)

2025-03-10 * "Shareholder distribution"
Assets:Bank:Operating -5000.00 USD
Equity:Distributions 5000.00 USD

Corporate-Level Estimated Tax (If applicable)

2025-04-15 * "1120-S entity-level estimate (BIG/passive tax)"
Assets:Bank:Operating -1200.00 USD
Assets:PrepaidTax:Federal 1200.00 USD

Marking Key Filing Dates

2026-03-15 note "E-filed 2025 Form 1120-S; furnished K-1s to all shareholders."

Sanity Checks (bean-query)

Use queries to ensure your records are sound.

Wages vs. Distributions YTD (Reasonable Comp Reality Check)

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

Did We Record the K-1 Handoff?

SELECT date, narration WHERE narration ~ "K-1";

Practical Tips (So the IRS Doesn’t Call) ✅

  1. Document "Reasonable Compensation." Keep a simple memo with your job duties, time allocation, and links to market salary data. Pay this amount via formal W-2 payroll.
  2. Separate Wages and Distributions Cleanly. Never mix them. Your Beancount ledger should make the distinction obvious.
  3. Watch State Rules. Be aware of minimum taxes (like in CA) or S-corp non-recognition (like in NYC).
  4. Revisit Estimates. If your income changes significantly mid-year, adjust both your personal 1040-ES and any S-corp level estimated payments.

This guide provides general information, not tax advice. Every business situation is different. Always consult with a qualified CPA for guidance specific to your circumstances.

S-Corp Tax Filing Deadlines (2025): A Crisp Guide for Beancount Users

· 5 min read
Mike Thrift
Mike Thrift
Marketing Manager

Filing taxes for your S-corporation involves a few key deadlines that you can't afford to miss. Staying on top of them prevents costly penalties and keeps your financial records clean. Here’s the short, accountant-friendly version of what to file, when it’s due, what happens if you’re late—and how to keep it all tidy in your Beancount ledger.


2025-07-25-s-corp-tax-filing-deadlines-2025

The Big Dates (for Calendar-Year S-Corps) 🗓️

For most S-corps operating on a standard calendar year, there are two primary dates to remember for your annual tax return, Form 1120-S.

  • Return Due Date: The deadline to file is Monday, March 17, 2025. The official due date is always the 15th day of the 3rd month after the tax year ends (March 15), but because that date falls on a Saturday in 2025, the IRS "next business day" rule pushes the deadline to Monday.
  • If You Need More Time: You can get an automatic 6-month extension by filing Form 7004 on or before the original March 17 deadline. This moves your filing due date to September 15, 2025. Remember, this is an extension to file, not an extension to pay any taxes owed.

Note for other filers: If you use a fiscal year, your return is due by the 15th day of the 3rd month after your tax year concludes. If your S-corp was dissolved, the final return is generally due by the 15th day of the 3rd month after the dissolution date.


What You Must Send to Shareholders

A core responsibility of an S-corp is to report each shareholder's portion of the company's income, deductions, and credits.

You must furnish a Schedule K-1 to every shareholder by the same day your Form 1120-S is due. This applies whether you file by the original deadline or an extended one. The K-1 provides the information shareholders need to file their personal tax returns.


Penalties You Actually Care About

The IRS imposes significant penalties for failing to file on time, so it pays to be punctual.

  • Late 1120-S: The penalty is 245permonth(orpartofamonth)foreachshareholder,forupto12months.Ifyour2024return(filedin2025)is60ormoredayslate,theminimumpenaltyincreasestothesmallerofthetaxdueor245 per month (or part of a month) for each shareholder**, for up to 12 months. If your 2024 return (filed in 2025) is **60 or more days late**, the minimum penalty increases to the smaller of the tax due or **510.
  • Late/Incorrect K-1s: Failing to furnish correct K-1s on time carries a penalty of $330 per schedule. If the failure is due to intentional disregard, the penalty can double or be 10% of the amounts required to be reported, whichever is greater.
  • Failure to Pay: Even if you file an extension with Form 7004, interest accrues on any tax due from the original March deadline. While most S-corps don't owe federal income tax, some can face corporate-level taxes in special situations.

If you get hit with a penalty, don't just pay it immediately. Check the IRS’s options for administrative penalty relief, such as first-time abatement or showing you had reasonable cause for the delay.


Corporate-Level Estimated Taxes (Edge Cases)

While S-corps are pass-through entities, they can sometimes owe entity-level taxes on things like built-in gains or excess net passive income. If your S-corp is expected to owe more than $500 for these taxes, you must make quarterly estimated tax payments.

For the 2025 calendar year, these installments are due on:

  • April 15, 2025
  • June 16, 2025 (June 15 is a Sunday)
  • September 15, 2025
  • December 15, 2025

Payments should be made through the Electronic Federal Tax Payment System (EFTPS).


Beancount Setup: Keep Filings and Payments Obvious

Use your ledger to create a clear audit trail of your tax compliance activities.

Starter Accounts

Assets:Bank:Operating
Assets:PrepaidTax:Federal ; For extension/estimate payments
Expenses:Tax:Federal:S-Corp ; For corporate-level tax owed
Liabilities:Tax:Federal:Payable
Equity:Distributions
Income:Sales

Mark the Filing and K-1 Handoff

Use note transactions to timestamp key compliance actions.

2025-03-10 note "Prepared 2024 Form 1120-S; K-1s ready for distribution."
2025-03-17 note "E-filed 2024 Form 1120-S; furnished all shareholder K-1s."

Recording an Extension

If you file for an extension without a payment (the common case):

2025-03-17 note "Filed Form 7004 to extend 2024 1120-S to 2025-09-15."

If you make an estimated payment with your extension (rare for S-corps):

2025-03-17 * "2024 1120-S extension payment (estimate)"
Assets:Bank:Operating -2000 USD
Assets:PrepaidTax:Federal 2000 USD

Recording a Final Tax Payment

If you end up owing corporate-level tax when you file:

2025-09-15 * "Settle 2024 S-corp tax due with return"
Assets:PrepaidTax:Federal -2000 USD
Expenses:Tax:Federal:S-Corp 2000 USD

Useful bean-query Checks

Verify your actions with simple queries.

  • Confirm you recorded the K-1 handoff:

    SELECT date, narration WHERE narration ~ "K-1s";
  • See all federal tax cash movements this year:

    SELECT SUM(position) WHERE account ~ "Tax:Federal|PrepaidTax:Federal" AND year = 2025;

Quick Checklist ✅

  • Put March 17, 2025, on your calendar to file Form 1120-S, or file Form 7004 by that date to get an extension.
  • Furnish Schedule K-1s to all shareholders by the same day you file your return (original or extended).
  • If applicable, schedule quarterly estimated payments for any corporate-level taxes.
  • Take deadlines seriously to avoid penalties, but seek penalty relief if something unavoidable slips through.

This guide provides general information and is not a substitute for professional tax advice. Consult with a qualified CPA to address your specific financial situation.

S-Corp “Reasonable Salary”: A Practical Guide for Beancount Users (2025)

· 6 min read
Mike Thrift
Mike Thrift
Marketing Manager

If you run an S-corp and work in it, the IRS expects you to take W-2 wages before you take owner distributions. The key phrase that governs this entire process is “reasonable compensation.” Getting this wrong can lead to costly tax adjustments and penalties.

Here’s what “reasonable” means in practice—and how to track it cleanly and defensibly in your Beancount ledger.

2025-07-24-s-corp-reasonable-salary


What the IRS Actually Requires

The rules are straightforward: shareholder-employees must be paid reasonable compensation for their services before receiving non-wage distributions. Paying yourself too little (or nothing at all) while taking large distributions is a major red flag. The IRS can, and often does, reclassify those distributions as wages, hitting you with back payroll taxes and penalties.

This isn't a new or obscure rule. The IRS has emphasized it for years, notably in its Fact Sheet FS-2008-25, which clarifies that corporate officers who perform more than minor services are to be treated as employees for FICA tax purposes. On your annual Form 1120-S, officer pay is reported on Line 7 (“Compensation of Officers”), and the instructions explicitly state that these amounts are considered wages to the extent they are for reasonable compensation.

Courts consistently back this up. In the landmark case Watson v. United States, a CPA paid himself a salary of only $24,000 while taking significant distributions from his profitable firm. The court sided with the IRS, recharacterizing most of those distributions as wages subject to employment taxes.


How to Estimate a Reasonable Salary (Simple, Defensible)

So, how do you determine a "reasonable" number? Think of it this way: what would you have to pay someone else to do the job you actually do, in your market, with your experience? The IRS views this as a valuation problem, and there are several common-sense ways to arrive at a defensible figure.

Here’s a pragmatic workflow:

  1. Start with Market Comps: This is your anchor. Use resources like Glassdoor, the Bureau of Labor Statistics (BLS), or salary ranges from recruiters to find data for comparable roles in your geographic area.
  2. Factor in Your Role & Time Split: Most small business owners wear multiple hats. Acknowledge this by weighting your salary based on the time you spend on different functions. For example, you might be 60% software engineer and 40% product manager.
  3. Perform an Ability-to-Pay Sanity Check: Your company's financial health matters. A business with losses may not be able to support a top-quartile salary. However, reporting zero wages while you perform substantial services is rarely justifiable.
  4. Document Everything: Save your sources, notes, and calculations. This documentation is your first line of defense in an audit. (More on this below.)

Quick Worksheet (Illustrative)

Let's walk through an example:

  • Market Pay: You find that the local median salary for a Senior Engineer is 140,000andforaProductManageris140,000** and for a Product Manager is **120,000.
  • Your Time Split: You estimate your time is 60% engineering and 40% product management.
  • Weighted Base Salary: (0.60times(0.60 \\times 140,000) + (0.40 \times 120,000)=120,000) = 84,000 + 48,000=48,000 = 132,000$.
  • Final Decision: Based on your company's current margins, you decide on a salary of $125,000 and plan to revisit it annually.

For context, the 2025 payroll tax rates are 6.2% for Social Security on wages up to $176,100 and 1.45% for Medicare on all wages. Both the employee and employer pay these amounts.


Common Pitfalls to Avoid

Steer clear of these common mistakes that can attract IRS scrutiny:

  • Taking Distributions Before Wages: If you provided services to your S-corp during the year, you must run payroll for your reasonable wages before taking any distributions.
  • Setting a "Token" Salary: A nominal salary—like $10,000 for a full-time officer of a highly profitable company—is a near-certain trigger for reclassification, as seen in the Watson case.
  • Mishandling >2% Shareholder Health Insurance: Premiums paid for health insurance for shareholders who own more than 2% of the company must be included in their W-2 wages. These amounts are subject to income tax but are generally exempt from FICA taxes. Coordinate with your CPA or payroll provider to ensure this is handled correctly.

A Clean Beancount Setup

Your ledger is the perfect tool for maintaining a clear line between wages and distributions.

Minimal Chart of Accounts

Assets:Bank:Operating
Expenses:Payroll:Wages
Expenses:Payroll:Employer:SocialSecurity
Expenses:Payroll:Employer:Medicare
Liabilities:Payroll:Withholding:Federal
Liabilities:Payroll:Withholding:SocialSecurity
Liabilities:Payroll:Withholding:Medicare
Equity:Distributions

Example Postings

This example shows a monthly payroll run for a 150,000annualsalary(150,000 annual salary (12,500/month), followed by a separate owner distribution. Notice how wages are recorded as a business expense, while distributions are a reduction of equity.

; Run monthly payroll (company side + withholdings)
2025-02-28 * "Payroll - February"
Assets:Bank:Operating -10350.00 USD
Expenses:Payroll:Wages 12500.00 USD
Expenses:Payroll:Employer:SocialSecurity 775.00 USD
Expenses:Payroll:Employer:Medicare 181.25 USD
Liabilities:Payroll:Withholding:Federal -3000.00 USD
Liabilities:Payroll:Withholding:SocialSecurity -775.00 USD
Liabilities:Payroll:Withholding:Medicare -181.25 USD

; Owner distribution (non-wage)
2025-03-10 * "Shareholder distribution"
Assets:Bank:Operating -5000.00 USD
Equity:Distributions 5000.00 USD

Useful Checks with bean-query

Periodically, you should compare your year-to-date wages against distributions. This query makes it easy:

; Compare wages vs. distributions YTD
SELECT account, SUM(position)
WHERE (account ~ "Expenses:Payroll:Wages" OR account ~ "Equity:Distributions")
AND year = 2025
GROUP BY account;

Paper Trail (Protect Yourself)

If the IRS ever asks, you'll want your reasoning documented.

  • Create a short compensation memo each year. Detail your roles, time split, links to market data you used, and the final salary you chose.
  • Store this memo in your Beancount directory, for example: docs/comp/YYYY/comp-memo.md.
  • Keep copies of all official payroll reports and your annual W-2/W-3 filings.
  • Record your decision directly in your ledger with a note entry.
2025-01-15 note "Set 2025 officer salary at $125,000 based on market comps + role split. See docs/comp/2025/comp-memo.md"

FAQ (Fast)

  • Can my salary be $0 if my company lost money? 📉 If you performed significant services, the IRS still expects you to be paid a reasonable wage for that work. If cash flow is a serious issue, get professional advice on how to proceed.
  • How often should I revisit my salary? 🗓️ At least annually. You should also reassess it anytime your role, responsibilities, or the market changes significantly.
  • What if I’m the only person in the company? 🙋 Even if you're a solo operator, you are still an employee of your S-corp. You must run formal payroll if you work in the business.

This guide provides general information and is not a substitute for professional tax advice. Always consult with a qualified CPA to address your specific financial situation.

S-Corp Election Deadline (2025): A Crisp Guide for Beancount Users

· 6 min read
Mike Thrift
Mike Thrift
Marketing Manager

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.

2025-07-23-s-corp-election-deadline-2025


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:DistributionsFor 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.