Dividends & Distributions 2025
Unpacking the "Classical System" of double taxation, the hidden traps of Earnings & Profits (E&P), and the strategic use of Stock Redemptions.
Executive Summary
The U.S. "classical system" subjects C Corporations to double taxation: once at the corporate level (21%) and again upon distribution. However, not all distributions are taxable dividends.
The character of a payout depends entirely on the corporation's Earnings and Profits (E&P). Without E&P, a distribution is a tax-free return of capital. Understanding this difference is the single most important factor in C Corp tax planning.
The Cost
The Gatekeeper
The Exit
The Waterfall (Section 301)
Ordering Rules
Earnings & Profits (E&P)
The "Nimble Dividend" Rule
Dividends are sourced first from Current E&P, calculated without regard to past deficits.
Common Adjustments
- Taxable Income Starting Point
- + Muni Bond Interest Add
- + Depreciation (ADS diff) Add
- - Federal Taxes Paid Subtract
- - 50% Meals/Entertainment Subtract
Redemptions (Section 302)
Sale vs. Dividend
A redemption is when the corp buys back your stock. If structured correctly (Sec 302), it's a Sale (Capital Gain + Basis Recovery). If not, it's a Dividend (No Basis Recovery).
Safe Harbors
- 1. Substantially Disproportionate: You must own <50% of voting power AND reduce your voting % to less than 80% of what it was before.
- 2. Complete Termination: You sell 100% of your stock. Warning: Family attribution (Sec 318) counts your parents/spouse/kids' stock as yours unless you file a waiver.
Interactive: E&P Waterfall Calculator
Calculate the tax character of a distribution based on the corporation's E&P status.
Financial Data
Can be negative.
Often negative in startups.