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Exam Review, 1099s and Tax Pro Education

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Propel Career Lab by Dinesen Learning
Propel Career Lab by Dinesen Learning
Exam Review, 1099s and Tax Pro Education
  • 1099 Reporting

    Form 1099-K, Part 3

    ByJason Dinesen September 8, 2026September 8, 2026

    Watch the companion podcast: This is the third and final installment in our 1099-K series. In prior parts, we touched on how, when paying expenses that could be subject to 1099-K reporting, you don’t issue a 1099. Usually we’re talking about contract labor/1099-NEC, but it could also be other types of payments. This requires tracking…

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  • Companion Notes

    Companion Notes: FIRE, Extinguished

    ByJason Dinesen September 1, 2026September 2, 2026

    The FIRE system is shutting down at 3 pm on November 19. Here are the slides used in the video version of the podcast. One of the complaints about IRIS is the 100-form limitation. IRIS has been updated now to accommodate up to 250 forms at a time when filing CSV files. This brings up…

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  • Filing Issues

    FIRE, Extinguished

    ByJason Dinesen September 1, 2026August 30, 2026

    The IRS has announced the official end to the FIRE system — 3 pm Eastern Time on November 19. We knew this day was coming, but we didn’t know exactly “when.” Now, we do. Background The FIRE system — Filing Information Returns Electronically — started many years ago (40 years ago, according to this IRS…

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  • Companion Notes

    Companion Notes: IRS Releases 2026 Substitute Forms Information

    ByJason Dinesen August 28, 2026August 28, 2026

    In this week’s blog post and podcast, I mentioned how there is a change to the address fields on 1099s, and how I am not sure if this is just cosmetic or not. The issue I am watching with this is, it might affect file specifications in IRIS (I am not sure yet — IRS…

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  • Filing Issues

    IRS Releases 2026 Substitute Forms Information

    ByJason Dinesen August 25, 2026August 25, 2026

    Podcast on this topic: The IRS has released its annual revenue procedure relating to substitute forms — Revenue Procedure 2026-18. (IRS later released a slight correction to page layouts, in Notice 2026-14.) What is a Substitute Form? A substitute form means an information return (such as a 1099) that is printed on something other than…

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  • Ask the Experts

    Ask the Experts, Volume 3

    ByJason Dinesen August 18, 2026August 17, 2026

    Question: We understand the IRS instructions for B-Notice mailings say: Your outside mailing envelope must be clearly marked “IMPORTANT TAX INFORMATION ENCLOSED” or “IMPORTANT TAX RETURN DOCUMENT ENCLOSED”. We also know this statement is required for some information reporting forms, and the second statement is used on our mailing envelopes. But – does this statement…

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  • 1099 Reporting

    New IRS FAQs on Overtime Have One Mention of 1099s

    ByJason Dinesen August 11, 2026August 20, 2026

    Listen to or watch the podcast on this topic: https://podcasts.dinesenmedia.com/show/information-return-intelligence-1/irs-releases-faqs-on-overtime-with-one-1099-item The IRS has released more frequently asked questions on the overtime deduction. Most of the new FAQs don’t apply to this audience, but there was one FAQ about 1099s: Q7. Under what circumstances is qualified overtime compensation reported on Form 1099-MISC or NEC instead of…

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  • 1099 Reporting

    Another Court Case Confirms: Attorney Fees are Included in Taxable Settlement

    ByJason Dinesen August 4, 2026August 20, 2026

    Listen to or watch the podcast on this topic: https://podcasts.dinesenmedia.com/show/information-return-intelligence-1/settlement-payments-attorney-fees-and-1099-reporting/ When you pay a settlement to another party, it is common for the settlement to include a portion that you must send to the other party’s attorney, as the attorney’s fee. When (if) you issue a 1099-MISC (box 3) to the other party, do you…

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  • 1099 Reporting

    Correction Deadline Approaching

    ByJason Dinesen July 28, 2026August 20, 2026

    Listen to or watch the podcast on this subject: https://podcasts.dinesenmedia.com/show/information-return-intelligence-1/correction-deadline-approaching-to-avoid-penalties/ A key deadline is looming for corrections of 1099s to avoid penalty. That deadline is August 1. Let’s examine. Late-Filing Penalties The IRS can assess penalties against you for filing a 1099 with incorrect information on it. This is true even if you filed the…

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  • Ask the Experts

    Ask the Experts, Volume 4

    ByJason Dinesen July 21, 2026August 20, 2026

    Listen to or watch the associated podcast: https://podcasts.dinesenmedia.com/show/information-return-intelligence-1/ask-the-expert-volume-4/ Question: I wanted to confirm my understanding on who was responsible for issuing 1099’s/1042-S’s for vendors that are paid by an e-payables credit card. If I recall correctly, these should be issued by the bank issuing the card, as they are the ultimate payor. Answer: You are…

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