Virtual Bootcamp on Latest IRS Form 1099-MISC and 1099-NEC Compliance

Event: Live Webinar
Event Date: August 02, 2023
Presenter: Jason T. Dinesen
Event Time: 11 am EST
Duration:4 Hours


Form 1099 compliance takes many forms, from determining what payments to report, to filing the forms on time, to dealing with IRS notices afterwards. And, with contract labor, there’s always the risk of the IRS auditing you and determining that your contractors should actually be employees. All of these items come with the risk of penalties.


Any business – regardless of its structure (sole proprietor, corporation, etc) that makes “reportable transactions” during the year is requires to issue 1099 to the recipient of income and to the IRS. Form 1099-MISC compliance is a surprisingly complicated compliance requirement for businesses and accountants. The requirements are always changing, and answers are seldom clear-cut. employee. This session includes the latest update on Form 1099-NEC which is being Resurrected by IRS & it will be used to report payments made to independent contractors. This session would cover :

  • What constitutes a reportable transaction?
  • What are the rules regarding paying and IRS reporting on Independent Contractors?
  • How do we avoid the IRS CP-2100 (B-Notices)? What if our vendor/payee claims exemption; must we obtain a W-9 anyway?
  • What are the best practices for handling our information reporting obligations?
  • How can we minimize risk of improper exemption claims by our payees and vendors?
  • Different due diligence procedures that shield an issuer from penalties even when the forms contain incorrect information.
  • This webinar is recommended for everyone professional in Accounting industry including Bank Managers, Compliance Officers, Information Reporting Officers, Tax Managers, CFOs, Controllers, Accounting Managers, Auditors, IT Managers, Compliance Managers, Risk Managers or every professional & team member in accounting practice.


Before changes, the Form W-4 was a critical form that all companies have to obtain from employees and has had special processing requirements. The form includes major revisions, including several new input elements for federal income tax withholding calculations, which will require significant reprogramming of payroll systems. This session will prepare the payroll professionals to understand the changes to the Form W-4 and to review the recently released draft of the W-4 Form. We will also discuss the IRS specific laws around the processing of Form W-4 and how they should be handled will be discussed. Apart from that, this webinar would cover :

  • The layout of the new Form W-4 and its requirements
  • Withholding using Forms W-4 vs withholding using forms
  • What to do with existing, “old” W-4s filled out by employees?
  • How to handle moving expenses?
  • Form 1099-NEC for reporting of independent contractors

This webinar will prepare your staff for this filing year, improve your employee reporting set-up and maintenance practices, and reduce your risk of complaints from the IRS.


Tax laws are constantly changing. Tax and financial professionals need to stay current to understand the impact of these changes and to minimize taxes. The Tax Cuts and Jobs Act changed the way tax is calculated for most taxpayers, including those with substantial income not subject to withholding, such as small and mid-size business owners. Among other reforms, the new law revised business expense deductions, increased the standard deduction, removed personal exemptions, increased the child tax credit and limited or discontinued certain deductions. This webinar would focus on business tax updates related to the CARES Act, including:

  • Treatment of net operating losses
  • Changes to certain depreciation rules
  • Update of pending tax legislation and other developments
  • Payroll Updates
  • Qualified Business Income(199A)
  • Payroll Updates
  • Paycheck Protection Program

This practical webinar provides a comprehensive update and an instant working knowledge of all key tax provisions. This session will get you up to speed on the latest developments related to individual, partnership, S corp, and C corp returns for 2020.

Session Highlights:

  • What is a 1099?
  • A (brief) tour of the types of 1099s that are out there
  • Determining thresholds — did you pay that contractor $600 or more?
  • What if you paid a corporation? A discussion of medical payments and legal payments.
  • What if you paid with a credit card or an app?
  • Reimbursements to contractors — included on the 1099 or not?
  • A tour of Form 1099-MISC — rent, royalties, and other 1099-MISC topics
  • State issues
  • How to file 1099s — including the new e-file mandate
  • Penalties for failure to file
  • Effectively using Form W-9 and other due diligence tips
  • Correcting forms with errors on them
  • IRS CP-2100 letters and sending B-Notices to your contractor
  • Backup withholding — the hidden “gotcha” in the 1099 world
  • Contractor versus employee — is that contractor really a contractor?
  • Relief options in an IRS audit
  • As time allows, discussion of other forms in the 1099 series that you might encounter

As time allows, discussion of other 1099 issues such as the question of, does the owner of a rental property issue 1099s to contractors?

Tax Expert Jason Dinesen has been very vocal on COVID-19 and has garnered great reviews for providing his insights to attendees. He has educated more than 10000 professionals so far on COVID-19 related topics. This 8 hour CPE webinar is going to be insightful experience for all the attendees

What You Get:

  • Training Materials
  • Live Q&A Session with our Expert
  • Participation Certificate
  • Access to Signup Community (Optional)
  • Reward Points

Who Should Attend:

  • Tax Attorney
  • Tax Practitioners
  • Accountant
  • CPA – Small Firm
  • CPA – Mid Size Firm
  • Accounting Firm
  • Tax Pros
  • CPA (Industry)
  • Tax Firm
  • Young CPA
  • Entrepreneurial CPA
  • Tax Accountant (Industry)
  • Tax Director (Industry)
  • Accounting Practice Owners
  • Senior Accountant
  • Accounts Director
  • Cloud Accountants
  • Chief Accounting Officer
  • Entrepreneurial Accountant
  • Tax Managers
  • Accounting Managers
  • Tax Preparer

Speaker Profile:

Jason Dinesen (EA, LPA) is a tax nerd,entrepreneur, tax expert and a well-known presenter of continuing education courses. Known for his sharp tax interpretations, he is one of the quickest to bring the analysis of the latest tax updates and IRS guidance to the professional community. Jason has coached over 200,000 accounting, tax, and HR professionals on various topics of accounting, individual taxation, corporate taxation, professional ethics and much more. He has presented over dozens of webinars on Form 1099 (for 10 years on this subject!); marriage in the tax code; tax updates; the new Form W-4, payroll updates, filing status, tax credit and other issues relating to the modern-day household setting. He also teaches 2 classes at Simpson College, Individual Income Tax and Business Analytics. Jason always had a knack for radio shows and has and regularly features as an anchor for Radio Iowa. Jason was born and raised in Iowa and has a degree in corporate communications from Simpson College in Indianola. He has a big family that includes his wife, two sons, 4 cats and 2 dogs. His other hobbies include being a season ticket holder to University of Iowa football.