Individual Tax Preparation for Investors

CPA for Investment Income and Stock Sales

Investment activity can turn a relatively straightforward individual tax return into something that deserves a closer look.

TaxReturn.cpa prepares individual returns involving stock and ETF sales, mutual funds, dividends, interest, capital gains and losses, multiple brokerage accounts, and other investment activity.

Know your price, see current production availability, and decide whether to move forward without scheduling a sales call.

See Your Price

Individual tax preparation starts at $650.

Investment Income Is More Than Dividends and Interest

A few Forms 1099-INT or 1099-DIV do not necessarily make a tax return complicated. Investment reporting becomes more involved when securities are sold, cost basis needs attention, transactions require adjustments, or activity is spread among several brokerage accounts.

Sales of stocks, ETFs, mutual funds and other investments may be reported on Form 1099-B. Those transactions can flow through Form 8949 and Schedule D, where short-term and long-term gains and losses are determined and adjustments may be required.

The objective is not simply to enter totals from a brokerage statement. The information has to be considered in the context of the rest of your individual tax return.

See the broader types of individual returns we handle on our What We Prepare page.

Where Investment Tax Returns Become More Complicated

Short-Term and Long-Term Capital Gains Are Different

How long you held an investment can affect how a gain is taxed.

In general, an investment held for one year or less before sale produces a short-term capital gain or loss. An investment held for more than one year generally produces a long-term capital gain or loss.

Net short-term capital gains are generally taxed as ordinary income, while net long-term capital gains may qualify for different federal tax rates.

When you have numerous transactions, the return has to properly combine short-term and long-term activity before determining the overall capital gain or loss.

Why Cost Basis Matters

Cost basis is generally the starting point for determining your gain or loss when an investment is sold. If the basis is wrong or missing, the taxable gain or deductible loss can also be wrong.

Brokerage firms report basis information for many covered securities, but not every investment transaction comes with complete basis information. Older holdings, transferred securities, inherited or gifted assets, and certain employer-stock transactions can require additional information.

When the basis reported to the IRS does not match the amount properly reportable on the tax return, Form 8949 provides mechanisms for reporting appropriate adjustments.

Your 1099-B May Not Be the Entire Story

Form 1099-B commonly reports proceeds from securities transactions and may also show cost basis, holding period and wash-sale information.

But the tax return still needs to determine how those transactions should be reported. Depending on the transaction, information may need to be summarized, separately reported, or adjusted on Form 8949 before flowing to Schedule D.

That is why we generally want the complete consolidated brokerage tax package rather than only a screenshot or one page showing total gains and losses.

What Is a Wash Sale?

The wash-sale rules can apply when you sell stock or securities at a loss and acquire substantially identical stock or securities within the period beginning 30 days before the sale and ending 30 days after the sale.

When the rule applies, the loss may be disallowed currently and generally becomes part of the basis of the replacement investment rather than simply disappearing.

Brokerage reporting may identify many wash sales automatically, but taxpayers with activity spread among different accounts or institutions can have additional facts that deserve attention.

What Happens if Your Investments Lost Money?

Capital losses are generally netted against capital gains as part of the Schedule D calculation.

If your allowable capital losses exceed your capital gains, individuals can generally deduct up to $3,000 of the excess net capital loss against other income each year ($1,500 if married filing separately).

Remaining allowable capital losses generally carry forward to future tax years. Prior-year returns can therefore be important when you have an existing capital-loss carryforward.

Do Your Stock Sales Come From RSUs or an ESPP?

Employer stock deserves additional attention because the brokerage transaction may connect directly to compensation already reported through payroll.

For restricted stock units, employee stock purchase plans and related stock-plan reporting, visit our CPA for RSU and ESPP Taxes page.

And if you moved between states while earning or vesting employer stock, see our CPA for Multi-State Tax Returns guide.

Investment Income We Commonly See

Depending on your situation, your individual return may include:

• Interest reported on Form 1099-INT
• Ordinary and qualified dividends reported on Form 1099-DIV
• Stock and ETF sales
• Mutual fund sales and distributions
• Short-term and long-term capital gains and losses
• Multiple brokerage accounts
• Form 1099-B transactions
• Cost-basis adjustments
• Wash-sale adjustments
• Capital-loss carryforwards
• RSUs and employee stock purchase plans
• Other investment activity requiring individual review

Certain investment situations—such as complex options activity, publicly traded partnerships, substantial cryptocurrency activity, foreign investments, or incomplete basis records—may require individual review before we determine whether the return fits the standard TaxReturn.cpa process.

Large Investment Gains Can Affect More Than the Return

A significant stock sale can create taxable income without any tax being withheld at the time of the transaction.

Depending on the amount of the gain and your other income and withholding, investment income can affect whether estimated tax payments should be considered during the year.

This is one reason tax planning can become more valuable as your investment activity becomes more significant.

How Much Does Tax Preparation With Investment Income Cost?

Having investment income does not automatically make a tax return complex.

A taxpayer with ordinary interest, dividends and a handful of well-reported stock sales is very different from someone with several brokerage accounts, hundreds of transactions, missing basis information, stock compensation and multi-state issues.

Our individual tax preparation pricing is based on the overall complexity of the return. Individual tax preparation starts at $650, and the See Your Price questionnaire considers your investment activity before you decide whether to engage us.

Professional Tax Preparation Without the Traditional CPA-Firm Guesswork

TaxReturn.cpa combines a digital client experience with the professional responsibility of a CPA firm.

Before becoming a client, you can answer a few questions about your tax situation, see your preparation price and view current production availability.

After engagement and payment, you'll choose an available production date and securely provide your tax documents, including your complete brokerage tax packages.

When all required information is complete by your production date, we expect to complete your return by the end of the third week following that date, subject to significant unexpected issues.

Learn how TaxReturn.cpa works →

Frequently Asked Questions About Investment Taxes

Do I need a CPA just because I have a brokerage account?

Not necessarily. Ordinary interest, dividends and straightforward brokerage activity can be relatively simple. Professional preparation becomes more valuable as the number and complexity of transactions increase or when basis, wash sales, stock compensation, multiple states or other tax issues are involved.

Do I have to report stock sales if I reinvested the money?

Generally, yes. Selling an investment is a tax event even if you immediately use the proceeds to purchase another investment. The gain or loss on the original sale still needs to be determined.

What if my 1099-B does not show cost basis?

Missing basis does not necessarily mean your basis is zero. Additional records may be needed to establish the appropriate basis before the transaction can be properly reported.

Can capital losses reduce my other income?

After capital gains and losses are netted, individuals can generally deduct up to $3,000 of an allowable net capital loss against other income each year, or $1,500 if married filing separately. Remaining allowable losses generally carry forward.

Can you prepare a return with several brokerage accounts?

Yes. Multiple brokerage accounts are common. The number of accounts, transactions and required adjustments helps determine the overall preparation level.

What if I have RSUs or an employee stock purchase plan?

We handle individual returns involving employer stock compensation. Because those transactions can connect W-2 compensation with brokerage reporting, see our RSU and ESPP tax preparation guide for more detail.

What brokerage documents should I provide?

Provide the complete consolidated tax package from each brokerage account rather than only selected pages. If basis is missing or a transaction involves employer stock, inherited or gifted investments, or transferred securities, additional records may also be needed.

Have Investment Income or Stock Sales?

You don't have to determine whether your investment activity makes your return Standard, Plus, Complex or something that needs individual review.

Answer a few questions about your tax situation and we'll show you your preparation level and price before you decide whether to move forward.

Know your price. See current production availability. Know when your return is expected to be completed.

See Your Price

Reviewed by Marc Boulanger, CPA | Updated September 2026

Related: RSU & ESPP Taxes  ·  Multi-State Tax Returns  ·  What We Prepare  ·  Pricing  ·  How It Works  ·  FAQs