Mastering 1099-B Reporting on Schedule D and Form 8949: Meeting Capital Gains Basis Reporting Challenges

Basis Adjustments, Reconciling Multiple 1099-B Forms, Recognizing Wash Sales, Real Estate Reporting and More

Recording of a 110-minute CPE webinar with Q&A

Conducted on Tuesday, August 1, 2017
Recorded event now available

This webinar will provide tax advisers with a comprehensive and practical guide to mastering the tax reporting of 1099 brokerage statements on Form 1040 Schedule D and Form 8949. The panel will go beyond the basics to offer an in-depth tutorial on making adjustments to reported asset basis and navigating specific challenges, such as reporting for high-volume and day traders, discerning dealer vs. investor questions for clients selling real estate, identifying wash sale issues, and preparing reconciliation schedules to support reporting variances on Form 8949.


Five years after the IRS began requiring brokers to report basis in securities sold by U.S. taxpayers during a calendar year, tax advisers continue to struggle with key tax compliance complexities. While some tax reporting for transactions involving covered securities is straightforward, advisers are often faced with complex calculations and time-consuming data collection and analysis.

Taxpayers are required to reconcile basis information provided by brokers on Form 1099-B with their calculations of gains and losses on Schedule D using Form 8949. However, this reconciliation also presents specific complications for tax advisers, particularly in situations where the client is a high-volume trader, has multiple brokerage accounts, has transactions that may have wash sale loss disallowance, or has investments in real estate.

There are numerous other complexities in reporting transactions involving capital assets. Taxpayers receiving assets through gift or inheritance can face significant challenges in determining basis, especially when the assets are foreign-based. Section 1202 small business stock can also present calculation and reporting issues.

Listen as our experienced panel provides a thorough and practical guide to the challenges of Form 1099-B reporting on clients’ 1040 returns. The panel will outline approaches to properly report capital gains and anticipate potential audit red flags and common cost basis reporting errors.


  1. Basis reporting requirements on Form 8949
  2. Basis adjustments to information reported on Form 1099-B
    1. Reconciliation of multiple 1099-B Forms
    2. High-volume traders and the mark-to-market election
    3. Bond amortization
  3. Basis reporting for real estate
  4. Basis in assets received by gift
  5. Section 1202 Small Business stock
  6. Illustration of reconciliation schedules and basis adjustments


The panel will discuss these and other important questions:

  • How should high-volume and professional traders manage their Form 8949 compliance duties? When would a mark-to-market election be beneficial in avoiding wash-sale loss disallowance rules?
  • Reporting real estate transactions on Form 8949 and Schedule D
  • Reconciling multiple brokerage accounts to avoid wash-sale loss disallowance
  • Reporting basis discrepancies in the adjustment columns of Form 8949

Learning Objectives

After completing this course, you will be able to:

  • Identify sources of information for making basis reporting adjustments on Form 8949
  • Determine when a volume trader should make a Section 475 mark-to-market election to avoid wash sale loss disallowance
  • Discern how to create a reconciliation schedule for multiple brokerage accounts reported on separate Form 1099-B reports
  • Recognize when wash sales across different brokerage accounts need to be reported on Schedule D
  • Reporting sales within a publicly traded partnership


Jolaine L. Hill, CPA, Director
Katz Sapper & Miller, Indianapolis

Ms. Hill is primarily responsible for tax compliance issues that include the technical review of tax returns. She is also charged with ensuring that the accounting staff remains current on tax issues. Her areas of specialization include taxation matters surrounding partnerships, S and C corporations, not-for-profits, construction contractors, and high-net-worth individuals. She is involved in planning and research assignments as well as special projects, including negotiations with the Internal Revenue Service regarding installment agreements and compromise offers.

EA Credit

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Recorded Event

Includes full event recording plus handouts.

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Program Materials

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Strafford is an IRS approved continuing education provider and this course is approved for 2 enrolled agent (EA) credit hours.

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Customer Reviews

Excellent seminar! It was efficient and the important topics were covered at just the right pace; no time was wasted covering information that the participants already knew.

Rhonda G. Williams, CPA

Barraclough & Associates

I appreciated the flow of the information offered and the ease at which I could follow the handouts.

Larry Bruck

WISS & Company

I liked the fact that there was more than one person presenting the material. It's nice to hear multiple perspectives.

Matt Bristow

Cover & Rossiter

I liked the concentration on specific issues and examples.

Edita Rimalovsky

Komisar Brady & Co.

I loved the tools and handouts. Every CPE class should offer these kind of tools.

Jackie Meyer

Sample and Bailey

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