Form 1099-K Reporting

• Introduction
• The Law - Learn it, Know it, Live it 00:
• What’s New In 1099 E-Filing - Big 1099/W-2 E-Filing Changes 00:06:41
• What’s New In 1099 E-Filing - Steps to Using IRIS 00:09:52
• What’s New: Form 1099-NEC 00:18:13
• 1099-NEC 00:23:39
• 1099-NEC Accountable Plans and Expense Reimbursements 00:24:10
• 1099-NEC and Fringe Benefits 00:26:45
• 1099-NEC/2025Fringe Benefits Updates 00:30:48
• 1099-NEC Box One 00:34:30
• Draft 2026 Form 1099-NEC 00:35:45
• Draft 2026 Form 1099-MISC 00:41:44
• 1099-MISC 00:44:32
• 1099-MISC Box One - Rent & Exceptions 00:49:38
• 1099-MISC Box One - Special Form 1099-S 00:50:49
• 1099-MISC Box Two - Extractive Industries 00:51:55
• 1099-MISC Box Two - Creative Industries 00:53:35
• 1099-MISC Box Two - I.P./Intellectual Property 00:53:47
• 1099-MISC Box Two - Royalty Type 00:54:52
• 1099-MISC Box Three - Prizes and awards 00:55:09
• 1099-MISC Box Three - 1099-MISC Box Three 00:56:06
• 1099-MISC Box Four 00:59:06
• 1099-MISC Box Six - Reportable Medical Payments 01:01:54
• 1099-MISC Box Six - No Corporate Exception 01:02:14
• 1099-MISC Box Six - Examples of Exceptions 01:02:49
• 1099-MISC Box Ten 01:03:54
• What’s New: Form 1099-K  01:07:21
• What’s New: Form 1099-DA 01:12:44
• What’s New: Form 1099-R  01:15:39
• Other July 2025 Updates with 1099/W-2 Implications – No Tax on Tips 01:17:13
• Other July 2025 Updates with 1099/W-2 Implications – No Tax on Overtime 01:18:42
• The “Other 1099’s”: The 1099-INT 01:20:17
• The “Other 1099’s”: The 1099-B 01:21:03
• The “Other 1099’s”: The 1099-DIV 01:22:16
• The “Other 1099’s”: The 1099-C 01:24:07
• The Key to 1099 Reporting Begins With The W-9 01:26:03
• Watch Those TIN’s 01:29:14
• Watch Those TIN’s Cont’d 01:29:17
• Form W-9 Solicitations As A Key Year-End Task 01:30:25
• Payee Refuses to Provide TIN: What Do You Do? 01:31:46
• Validating Data – Problem Payees - U.S. Corporations 01:
• Validating Data – Problem Payees - The LLC 01:32:17
• Validating Data – Problem Payees - The LLC as the Disregarded Entity 01:32:55
• Validating Data – The Exempt Organization 01:33:24
• Validating Payee Data – TIN Match Program 01:34:31
• Watch Out For The Middleman 01:35:22
• Protect Yourself 01:37:24
• Attendee Questions 01:37:56
• Presentation Closing 01:43:52

• 

  Steven Mercatante

  Steven Mercatante is the principal and founder of TIR Consulting, LLC. He is a nationally recognized leader in tax reporting education and consulting on specialized compliance issues. He has conducted on-site consultation for corporate clients from across the world and led countless seminars and web [...]

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• Accountable Plan 00:28:06
• Audit 00:01:26, 00:18:07
• Backup Withholding 00:19:39, 00:56:08, 01:30:34
• B-Notice 00:18:01
• B-Notice 01:3
• Compensatory Damages 00:57:45
• CP-2100 00:18:00
• DBA -Doing Business As 01:27:28
• De Minimis Fringe Benefits 00:30:11
• Disregarded Entity 01:27:26
• Due Diligence 00:20:21,01:31:40,  01:35:33
• EIN 01:27:39, 01:33:06
• Exempt 00:57:24, 01:33:49
• Expense 00:53:06
• Expense Reimbursements 00:24:47, 00:30:49, 01:04:34
• Fair Labor Standards Act (FLSA) 00:38:47
• Fair Market Value (FMV) 00:28:38
• Fair Market Value (FMV) 00:55:37
• FIRE - File Information Returns Electronically 00:07:07 00:11:09
• Form 1099-B 01:21:06
• Form 1099-C 01:24:07
• Form 1099-DA 01:12:44
• Form 1099-DIV 01:22:16
• Form 1099-INT 00:46:59, 01:20:18
• Form 1099-K 01:07:23
• Form 1099-MISC 00:18:30, 00:24:25, 00:41:44, 01:03:48, 01:18”39
• Form 1099-NEC 00:16:16, 00:18:30, 00:20:39, 00:34:30, 00:46:33, 00:51:49, 00:55:18
• Form 1099-R 01:15:45
• Form 1099-S 00:50:59
• Form 8809 00:17:20
• Form W-2 00:00:03, 00:07:00, 00:16:20, 00:28:10, 00:38:29, 01:18:34
• Form W2-G 00:46:50, 00:47:42
• Form W-9 01:26:04
• Fringe Benefit 00:24:47, 00:27:59, 00:30:48, 00:31:27
• General Services Administration (GSA) 00:48:07
• Golden Parachute Payments 00:49:07
• Independent Contractor 00:13:00, 00:23:51, 00:26:30, 00:43:36
• Information Returns Intake System (IRIS) 00:08:49, 00:09:49, 00:11:10, 00:14:05
• Intellectual Property (IP) 00:53:48
• IRC Section 132 00:30:07
• IRC Section 3406(a) 00:03:24, 00:05:42, 00:21:07
• IRC Section 6041(a) 00:03:24, 00:05:42, 01:31:59
• IRC Section 6045 00:03:24, 00:05:42, 00:
• IRC Section 6109(a)(2) 01:31:56
• IRC Section 6724 00:03:39
• IRS Notice 972CG 00:18:03
• Limited Liability Company (LLC) 00:50:26, 01:27:26, 01:32:39
• Overtime 00:38:51, 00:42:19, 01:17:16
• Personal Property  00:49:48
• Punitive Damages 00:57:46
• Real Property 00:49:49
• Reasonable Cause 01:31:02
• Safe Harbor 00:38:15
• Shareholder 01:18:13
• Sole Proprietor 01:27:33
• Stakeholders 00:13:33
• Tax Cuts and Jobs Act 00:30:54
• Tax Exempt Organization Search Tool 01:33:32
• Tax Gap 00:01:36
• TIN 01:26:25, 01:30:33
• TIN Match Program 01:34:35
• Transmitter Control Code (TCC) 00:09:34, 00:10:10
• Travel Expense 00:24
• Vendor 00:10:50, 00:12:35, 00:48:22

Accountable Plan: An accountable plan is a plan that follows the Internal Revenue Service (IRS) regulations for reimbursing workers for business expenses in which reimbursement is not counted as income. ... However, these expenses must be business-related to fall under an accountable plan.

Audit: A formal examination of an organization's or individual's accounts or financial situation

B-Notice: A notice from the IRS stating that one or more tax ID numbers were missing from a 1099 or do not match the IRS records.

Backup Withholding: Backup withholding is the tax that is levied on investment income, at an established tax rate, as the investor withdraws it. Backup withholding helps to ensure that government tax-collecting agencies (such as the IRS or Canada Revenue Agency) will be able to receive income taxes owed to them from investors' earnings. (www.investopedia.com)

CP-2100: It is a notice that tells a payer that he or she may be responsible for backup withholding. It is accompanied by a listing of missing, incorrect, and/or not currently issued payee TINs. Largevolume filers will receive a CD or DVD data file CP2100, mid-size filers receive a paper CP2100, andsmall filers receive a paper CP2100A.

Compensatory Damages: A sum of money awarded in a civil action by a court to indemnify a person for the particular loss, detriment, or injury suffered as a result of the unlawful conduct of another. Compensatory damages provide a plaintiff with the monetary amount necessary to replace what was lost, and nothing more.

DBA -Doing Business As: Sometimes it makes sense for a company to do business under a different name. To do this, the company has to file what's known as a DBA, meaning "doing business as." A DBA is also known as a "fictitious business name," "trade name," or "assumed name."

De Minimis Fringe Benefits: De minimis fringe benefits are low-value perks provided by an employer; de minimis is legal Latin for "minimal". Perks that are determined to be de minimis fringe benefits may not be accounted or taxed in some jurisdictions as having too small value and too complicated an accounting.

Disregarded Entity: A disregarded entity refers to a business entity with one owner that is not recognized for tax purposes as an entity separate from its owner. A single-member LLC ( “SMLLC”), for example, is considered to be a disregarded entity. (www.pntax.com)

Due Diligence: Due diligence is a process or effort to collect and analyze information before making a decision or conducting a transaction so a party is not held legally liable for any loss or damage. The term applies to many situations but most notably to business transactions.

EIN: The Employer Identification Number, also known as the Federal Employer Identification Number or the Federal Tax Identification Number, is a unique nine-digit number assigned by the Internal Revenue Service to business entities operating in the United States for the purposes of identification.

Exempt : Exempt employee is a term that refers to a category of employees set out in the Fair Labor Standards Act. They do not receive overtime pay, nor do they qualify for the minimum wage

Expense: Offset (an item of expenditure) as an expense against taxable income.

FIRE - File Information Returns Electronically: The IRS FIRE system is the electronic network used to accept and process most types of filing forms. Technically, it stands for File Information Returns Electronically.

Fair Labor Standards Act (FLSA): The Fair Labor Standards Act of 1938 29 U.S.C. § 203 is a United States labor law that creates the right to a minimum wage, and "time-and-a-half" overtime pay when people work over forty hours a week. It also prohibits most employment of minors in "oppressive child labor".

Fair Market Value (FMV): The term fair market value is used throughout the Internal Revenue Code among other federal statutory laws in the USA including Bankruptcy, many state laws, and several regulatory bodies. In litigation in many jurisdictions in the United States, the fair market value is determined at a hearing.

Form 1099-B: Proceeds From Broker and Barter Exchange Transactions is an Internal Revenue Service (IRS) tax form that is issued by brokers or barter exchanges. The form lists the gains or losses of all broker or barter exchange transactions.

Form 1099-C: According to the IRS, nearly any debt you owe that is canceled, forgiven or discharged becomes taxable income to you. You'll receive a Form 1099-C, "Cancellation of Debt," from the lender that forgave the debt.

Form 1099-DA: This form is specifically designed to handle the reporting for cryptocurrency and digital assets.

Form 1099-DIV : Form 1099-DIV: Dividends and Distributions is an Internal Revenue Service (IRS) form sent to investors who receive distributions from any type of investment during a calendar year. Investors can receive multiple 1099-DIVs. Each Form 1099-DIV should be reported on an investor's tax filing.

Form 1099-INT: Form 1099-INT is the IRS tax form used to report interest income. The form is issued by all payers of interest income to investors at year end and includes a breakdown of all types of interest income and related expenses. Payers must issue Form 1099-INTs for any party to whom they paid at least $10 of interest during the year.

Form 1099-K: A payment settlement entity (PSE) must file Form 1099-K for payments made in settlement of reportable payment transactions for each calendar year. A PSE makes a payment in settlement of a reportable payment transaction, that is, any payment card or third party network transaction, if the PSE submits the instruction to transfer funds to the account of the participating payee to settle the reportable payment transaction.

Form 1099-MISC: The Form 1099-MISC is an Internal Revenue Service (IRS) tax return document used to report miscellaneous payments made to nonemployee individuals, such as independent contractors, during the calendar year. (www.shrm.org)

Form 1099-NEC: In the context of 1099 tax filing, NEC stands for “Nonemployee Compensation” (the first letters of the three words None, Employee and Compensation). Most tax payers recognize NEC as box 7 on Form 1099-MISC. NEC is used to report income paid to independent-contractors / the-self-employed (referred to as 1099 employees for simplification purposes). So, while employers report income that gets paid to employees on Box 1 (Wages, tips, other compensation) of the W2 form, payers report income that gets paid to none-employees on Box 7 (NEC) of the 1099-MISC form. As an individual, if you received form 1099-MISC instead of Form W-2 then the payer did not consider you an employee and did not withhold income tax or social security and Medicare tax.

Form 1099-R: Form 1099-R is a tax form from the Internal Revenue Service (IRS) for reporting distributions from annuities, profit-sharing plans, retirement plans, IRAs, insurance contracts, or pensions.

Form 1099-S: A Form 1099-S is a tax document used to ensure that the full amount received for a real estate sale of some kind is accurately reported. A 1099-S can also be used to report income made on a rental property or investment property. For selling real estate, the buyer must complete and file their own 1099-S.

Form 8809: Use Form 8809 to request an initial or additional extension of time to file only the forms shown on line 6 for the current tax year.

Form W-2: Form W-2 is an Internal Revenue Service tax form used in the United States to report wages paid to employees and the taxes withheld from them. Employers must complete a Form W-2 for each employee to whom they pay a salary, wage, or other compensation as part of the employment relationship. - Wikipedia (https://en.wikipedia.org/)

Form W2-G: File this form to report gambling winnings and any federal income tax withheld on those winnings. The requirements for reporting and withholding depend on: the type of gambling, the amount of the gambling winnings, and. generally the ratio of the winnings to the wager.

Fringe Benefits: An extra benefit supplementing an employee's salary, for example, a company car, subsidized meals, health insurance, etc.

General Services Administration (GSA): The General Services Administration is an independent agency of the United States government established in 1949 to help manage and support the basic functioning of federal agencies.

Golden Parachute Payments: Golden parachute payments are payments of compensation made to individuals whose companies experience a change in control

IRC Section 132: Internal Revenue Code Section 132(a) provides eight types of fringe benefits that are excluded from gross income

IRC Section 6109(a)(2): Requires that a payee provide a TIN to the payer when the payment will be reportable on an information return.

IRC Section 6724: I.R.C. § 6724(a) Reasonable Cause Waiver — No penalty shall be imposed under this part with respect to any failure if it is shown that such failure is due to reasonable cause and not to willful neglect.

Information Returns Intake System (IRIS): The Information Returns Intake System (IRIS) Taxpayer Portal is a system that provides a no cost online. method for taxpayers to electronically file Form 1099 series. The Taxpayer Portal allows you to enter. data to create Forms 1099 by either keying in the information or uploading a .csv file.

Intellectual Property (IP): Intellectual property (IP) refers to creations of the mind, such as inventions, literary and artistic works, designs, and symbols, which are protected by law through exclusive rights granted to the owner for a limited time. The main types of IP protection are patents for inventions, copyrights for creative works, trademarks for brand identifiers, and trade secrets for confidential business information. IP rights serve to provide financial incentives for innovation, drive economic growth, and allow creators to control and benefit from their works.

Limited Liability Company (LLC): An LLC is a corporate structure where members cannot be held accountable for the company’s debts or liabilities. This can shield business owners from losing their entire life savings if, for example, someone were to sue the company. Can be a single member (much like a sole proprietor) or a multi-member. It shares certain traits of both corporations as well as partnerships or sole proprietorships. It is not a corporation.

Overtime: Overtime is time and a half of what an employee earns for every hour worked over 40 in a workweek. The FLSA salary threshold is the minimum salary employers must pay employees for them to be exempt from overtime wages.

Personal Property: Personal property is something that you could pick up or move around. This includes such things as automobiles, trucks, money, stocks, bonds, furniture, clothing, bank accounts, money market funds, certificates of deposit, jewels, art, antiques, pensions, insurance, books, etc.

Punitive Damages: Punitive damages, or exemplary damages, are damages assessed in order to punish the defendant for outrageous conduct and/or to reform or deter the defendant and others from engaging in conduct similar to that which formed the basis of the lawsuit.

Real Property: Real property is land and any property attached directly to it, including any subset of land that has been improved through legal human actions. Examples of real properties can include buildings, ponds, canals, roads, and machinery, among other things

Reasonable Cause : Reasonable cause is based on all the facts and circumstances in your situation. The IRS will consider any reason which establishes that you used all ordinary business care and prudence to meet your federal tax obligations but were nevertheless unable to do so.

Safe Harbor: A safe harbor is a provision of a statute or a regulation that specifies that certain conduct will be deemed not to violate a given rule. It is usually found in connection with a vaguer, overall standard. Under the safe harbor, a “rental real estate enterprise” is treated as a trade or business for purposes of Sec. 199A if at least 250 hours of services are performed each tax year with respect to the enterprise. ... The safe harbor requires that separate books and records be maintained for the rental real estate enterprise.

Shareholder: A shareholder is an individual or institution that legally owns one or more shares of stock in a public or private corporation. Shareholders may be referred to as members of a corporation.

Sole Proprietor: A business that legally has no separate existence from its owner. The sole proprietorship is the simplest business form under which one can operate a business. The sole proprietorship is not a legal entity. It simply refers to a person who owns the business and is personally responsible for its debts.

TIN: A Taxpayer Identification Number is an identifying number used for tax purposes in the United States and in other countries under the Common Reporting Standard. In the United States, it is also known as a Tax Identification Number or Federal Taxpayer Identification Number.

TIN Match Program: TIN Matching is part of a suite of Internet-based pre-filing e-services that allows “authorized payers” the opportunity to match 1099 payee information against IRS records prior to filing information returns.

Tax Cuts and Jobs Act: The Act to provide for reconciliation pursuant to titles II and V of the concurrent resolution on the budget for fiscal year 2018, Pub.L. 115–97, is a congressional revenue act of the United States originally introduced in Congress as the Tax Cuts and Jobs Act, that amended the Internal Revenue Code of 1986.

Tax Exempt Organization Search Tool: Tax Exempt Organization Search helps users find information about a tax-exempt organization’s federal tax status and filings.

Tax Gap: The gross tax gap is the difference between true tax liability for a given tax year and the amount that is paid on time. It is comprised of the nonfiling gap, the underreporting gap, and the underpayment (or remittance) gap.

Transmitter Control Code (TCC): The Transmitter Control Code (TCC) is an identifier that the IRS uses to distinguish different electronic filing companies. It's necessary when you need to file for a correction. Getting a TCC depends on how you file your 1099 forms

Travel Expense: Travel expenses are costs associated with traveling for the purpose of conducting business-related activities. Travel expenses can generally be deducted by employees as non-reimbursed costs incurred while traveling away from home specifically for business purposes.

Vendor: A vendor is a person or business that supplies goods or services to a company. Another term for the vendor is the supplier. In many situations, a company presents the vendor with a purchase order stating the goods or services needed, the price, delivery date, and other terms.