They can absolutely change from no withholding to withholding if they want. Its all reported as income anyways. Id be more concerned about whether this should be taxable at all. Some job training isnt imputed income if its required for your current position (not future advancement).

I'd strongly recommend getting this resolved in writing with HR before they make the withholding. The fact that your contract explicitly states "no withholding will be taken from your paycheck" creates a legal issue if they proceed without your agreement to modify the terms. When you meet with HR, ask them to explain: 1) Why they're changing the tax reporting method from 1099-MISC to what sounds like W-2 treatment, 2) Whether your company has a Section 127 educational assistance program that might make this training tax-free, and 3) How they plan to handle the contract discrepancy. If the training was truly mandatory for your current role and doesn't provide portable credentials for other jobs, there's a good chance it shouldn't be taxable imputed income at all. The IRS generally considers employer-provided training non-taxable when it's primarily for the employer's benefit and required for the employee's current duties. Document everything from this meeting and get their responses in writing. If they insist on proceeding with withholding despite the contract language, you may want to consult with an employment attorney about whether they're breaching your agreement.

Quick question for anyone who's dealt with this recently - I'm using TurboTax Business for my S-Corp and personal returns. Does it automatically handle the NOL carryforward worksheets and calculations between tax years? Or do I need to manually track this somewhere?

I'm dealing with a similar S-Corp NOL situation and wanted to add some practical tips from my experience last year. Make sure you have good documentation of your stock basis before claiming the loss - the IRS can challenge NOL deductions if you can't prove sufficient basis in your S-Corp stock. Keep detailed records of any loans you made to the company, capital contributions, and prior year income/losses. These all affect your basis calculation and determine how much of the NOL you can actually deduct. I had to reconstruct three years of basis calculations when the IRS questioned my NOL deduction. Also, consider whether the Section 199A QBI deduction might interact with your NOL situation in future profitable years. The interplay between NOLs and QBI can be complex, so it's worth understanding now while you're setting up your tracking systems. One more thing - if your photography business picks up significantly next year, be aware of the potential Section 461(l) excess business loss limitation. It caps business losses at $270,000 for single filers, with excess amounts treated as NOLs subject to the 80% limitation in future years.

anyone else notice how the systems always act up during peak filing season? like clockwork 🤡

I went through the exact same thing last month! The change from "non-filing" to "no record of return filed" is actually progress - it means the IRS is actively updating their system for the 2024 tax year. When I saw this status change, my return showed up in the system about 10 days later with a 971 notice code, then processed within another week after that. The key thing is that you're now in their queue and they're looking for your return. Keep checking your Account Transcript (not just W&I) every few days - that's where you'll see the real processing updates with the 150/846 codes when your refund gets approved.

has anyone else noticed the irs is super quick to cash checks but takes forever to process refunds? lol typical government efficiency at work 🙄

Just wanted to share my experience from last year that might help ease your anxiety. I was in almost the exact same situation - freelance web developer who owed about $4,200 and mailed in a paper return with a check. The IRS cashed my check within a week, but I didn't hear anything else for almost 2 months. I was starting to panic thinking something went wrong, but then I got a simple notice in the mail confirming my return was processed and accepted. No issues, no additional payments needed - just confirmation that everything was handled correctly. The key thing I learned is that payment processing and return processing really are separate departments with different timelines. Your check being cashed is actually a positive sign - it means they received your package and the payment amount matched what you indicated you owed. If there were obvious problems with your return, they typically wouldn't process the payment. For peace of mind, you can check "Where's My Refund" on the IRS website even though you're not getting a refund - it will eventually show your return status once it's fully processed.

FYI - I've been using TurboTax Self-Employed for a few years, and it actually has a really good section on handling mixed business/personal travel. It asks a series of questions about your initial intent, percentage of time spent on business, and walks you through what documentation you need.

As someone who's been through several IRS audits as a freelancer, I can confirm that the key is really in the documentation. For your situation, I'd recommend creating a detailed timeline of your Miami trip showing exactly when personal time ended and business activities began. One thing I learned the hard way - the IRS is surprisingly reasonable about these situations IF you can prove legitimate business necessity. Since your clients had emergencies that required immediate attention, that's actually strong evidence that the business portion was necessary, not just convenient. For the original flight, there's actually some flexibility here that others haven't mentioned. If you can show that a significant portion of your trip became business-focused due to unforeseen circumstances (which it sounds like you can), you may be able to allocate part of the transportation costs. I'd suggest consulting with a tax professional on this specific point since it's more nuanced than the standard "initial intent" rule. Document everything with timestamps - client emails, call logs, work deliverables completed during the trip. The conference room rental and extended hotel stays are slam dunks for deduction since they were purely business-driven expenses.