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

A live 110-minute CPE webinar with interactive Q&A

Tuesday, August 1, 2017 (in 9 days)
1:00pm-2:50pm EDT, 10:00am-11:50am PDT

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.

Registration per Person for Live Event

Additional lines for this conference can be purchased at 25% off. For orders of five or more lines, further discounts will apply and will be automatically reflected in the cart.

Live Webinar $147.00

Live Webinar & CPE Processing $182.00

CPE per Person on Live Event

Continuing Professional Education credit processing is available for an additional fee. CPE processing must be ordered prior to the event. To qualify for CPE you may not listen via the telephone.

This program is eligible for 2.0 CPE credits.

  • Field of Study: Taxes.
  • Level of Knowledge: Intermediate.
  • Advance Preparation: None.
  • Teaching Method: Seminar/Lecture.
  • Delivery Method: Group-Internet (via computer).
  • Attendance Monitoring Method: Attendance is monitored electronically via a participant's PIN and through a series of verification codes announced throughout the presentation.
  • Prerequisite: Three years+ business or public firm experience at mid-level within the organization, preparing complex tax forms and schedules, supervising other preparers/accountants. Specific knowledge and understanding of capital gains calculations, recognizing basis reporting on a Form 1099-B; familiarity with mark-to-market election rules and wash sale disallowance rules, and distinguishing between dealer and investor for purposes of evaluating real estate activities

NOTE: CPE credit processing for all attendees must be ordered by 2pm Eastern the day of the program to receive a Certificate of Attendance within 24 hours.


Recorded Event

Includes full event recording plus handouts (available after live webinar).

Note: Self-study CPE and EA credits are not offered on recorded events.

Recorded Webinar Download $147.00
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Recorded Audio Download (MP3) $147.00
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DVD (Slide Presentation with Audio) $147.00 plus $9.45 S&H
Available ten business days after the live event

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Registration Plus Recorded Event

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Recorded Webinar Download Only $47.00 with Registration/Webinar Combo

Live Webinar & Audio Download $194.00

Recorded Audio Download (MP3) Only $47.00 with Registration/MP3 Combo

Live Webinar & DVD $194.00 plus $9.45 S&H

DVD (Slide Presentation with Audio) Only $47.00 with Registration/DVD Combo


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EA Credit

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

I liked the concentration on specific issues and examples.

Edita Rimalovsky

Komisar Brady & Co.

I purchased the conference a few minutes after it began and the customer service rep was very helpful and got me signed up and logged into the conference very quickly.

Joanna Johnston

Savas Greene & Company

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

Jackie Meyer

Sample and Bailey

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

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WISS & Company

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