Understand the tax rules around investment decisions.
These connected guides explain taxable-account gains and distributions, loss harvesting, IRA conversions, and retirement withdrawals using primary IRS and SEC sources. They provide education—not individualized tax preparation or a promise that one strategy will lower your tax.
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Connected guides
Federal
Core scope
IRS + SEC
Primary sources
Start with the framework
Taxes are one part of the investing decision.
Account type, adjusted basis, holding period, distribution character, and the full tax return determine treatment. Tax considerations should be coordinated with diversification, risk, liquidity, costs, and the investor’s actual financial goal.
Capital Gains Taxes: Basis, Sales, and Reporting
A taxable investment sale generally creates a capital gain or loss equal to the amount realized minus adjusted basis, but holding period, netting, and reporting rules determine the federal tax treatment.
Read guideShort-Term vs. Long-Term Capital Gains
Federal tax law generally treats gains from capital assets held one year or less as short-term and gains from assets held more than one year as long-term, with different rate structures and netting rules.
Read guideTax-Loss Harvesting and the Wash-Sale Rule
Tax-loss harvesting realizes an investment loss that may offset capital gains or enter the capital-loss calculation, but the wash-sale rule can disallow the current loss when substantially identical securities are acquired around the sale.
Read guideQualified Dividends vs. Ordinary Dividends
Qualified dividends are included within ordinary dividends reported to the investor but may qualify for federal long-term capital-gain rates when issuer, holding-period, and related requirements are met.
Read guideETF Taxes: Distributions and Sales
In a taxable account, an ETF investor can face tax from cash distributions, capital-gain distributions, and gains realized when shares are sold; the ETF structure does not make every fund or transaction tax-free.
Read guideRoth Conversions: Taxes, Timing, and Records
A Roth conversion moves eligible traditional retirement assets into a Roth IRA and can make part or all of the converted amount taxable as ordinary income for that year; it is not the same as a regular contribution.
Read guideBackdoor Roth IRA Guide
The commonly used term “backdoor Roth IRA” describes a nondeductible traditional IRA contribution followed by a Roth conversion; each step is governed by existing IRA contribution, conversion, aggregation, and reporting rules.
Read guideRetirement Withdrawal Order
There is no universal retirement withdrawal order: taxable accounts, traditional retirement accounts, Roth accounts, required distributions, benefits, spending, and estate goals interact across multiple tax years.
Read guideSuggested path
Transactions first, accounts next.
- 1. Taxable investing: Learn basis, holding periods, losses, and dividends.
- 2. Funds: Connect ETF distributions and share sales to reporting.
- 3. IRAs: Separate contributions, conversions, basis, and withdrawals.
- 4. Retirement: Coordinate withdrawals across tax years and account types.