Have you considered looking into other assistance programs instead of potentially risky tax situations? There are programs specifically designed to help people in your situation while waiting for disability approval. Many states have emergency assistance for families with newborns. Also, there are charities that help with car repairs for people who need transportation for medical reasons. These might be better options than depending on tax strategies that could cause problems later.

I understand you're in a tough financial situation, especially with a new baby and needing reliable transportation for medical appointments. However, I'd strongly encourage you to be very careful about the dependent claiming situation. From what you've described about your previous experience, it does sound like it may not have been entirely legitimate. The IRS dependent rules are strict - your sister would need to provide MORE than half of your total support for the entire year, and you'd need to meet the income requirements. Given that you mentioned having a baby recently, you might actually qualify for some additional tax credits yourself if you file your own return (like the Child Tax Credit), which could be more beneficial than being claimed as someone else's dependent. Before making any decisions, I'd really recommend getting professional advice. You could use one of the free tax preparation services available to low-income individuals, or even contact the IRS directly to understand your specific situation. The last thing you want is to face penalties or have to pay back benefits later when you're already struggling financially. Have you looked into local assistance programs for new parents or people awaiting disability approval? Many communities have emergency assistance funds specifically for situations like yours.

Have you considered asking the company to reclassify you as an employee instead of a contractor? If you were working regular hours at their location using their equipment, you might actually legally be an employee not a contractor. Companies sometimes misclassify workers as contractors to avoid paying employment taxes and benefits. It's actually pretty common in retail. If you were treated like a regular employee in practice, you might have been misclassified. Just something to consider if you're still working there or plan to in the future!

Just wanted to chime in as someone who went through this exact situation a couple years ago! I worked what felt like a regular retail job but got hit with a 1099-NEC at tax time. One thing I wish I'd known earlier - even though you have to file Schedule C and pay self-employment tax, you might qualify for the Qualified Business Income (QBI) deduction under Section 199A. This can give you up to a 20% deduction on your self-employment income, which helps offset some of that extra tax burden. Since your income was only $2,100, you should definitely qualify (the income limits are much higher). Most tax software will calculate this automatically once you enter your Schedule C info, but it's worth double-checking that it's being applied. Also, definitely track ANY expenses related to this work - even small things like work shirts, phone usage, or gas for work trips add up. I missed out on probably $200-300 in deductions my first year because I didn't think they mattered. Every little bit helps when you're dealing with that 15.3% self-employment tax on top of regular income tax!

I've been following this thread and wanted to add my perspective as someone who went through a very similar situation. The "wait and report after leaving" strategy mentioned by others is actually quite effective, but I'd also suggest documenting everything NOW while you're still there. Start keeping detailed records of: your work schedule, any emails showing you're required to be in the office, descriptions of your ongoing duties vs. project-based work, and any communications about your employment status. Take screenshots of job postings if they advertised your position differently than how you're classified. This documentation will be crucial whether you decide to approach your employer directly, file with the IRS, or report after finding a new job. I made the mistake of not documenting enough in my situation, and it made proving my case much harder later. Also, consider checking if your company has an HR department or if decisions are made by one person. Sometimes the person doing payroll doesn't fully understand classification rules, and bringing it to HR's attention (framed as a compliance question) might resolve it without drama. But definitely have that documentation ready first, just in case.

One thing I haven't seen mentioned here is checking if your company has any policies or employee handbook that might inadvertently contradict your contractor classification. Many employers slip up by including 1099 workers in employee-only policies or expecting them to follow the same rules as W-2 staff. Also, since you mentioned the other admin has been there 12 years, that's actually a huge red flag for the IRS. Long-term "contractor" relationships, especially for ongoing administrative work, are classic misclassification cases. The IRS specifically looks for situations where someone performs the same role for years as evidence of an employer-employee relationship rather than true independent contracting. You might want to research what happened to other companies in your industry who got caught doing this. Sometimes showing your employer news articles about similar businesses facing penalties can be more persuasive than citing IRS regulations directly. It makes the risk feel more real and immediate. And honestly, given that you're new and they've been misclassifying the other admin for over a decade, this company is probably sitting on a pretty significant tax liability if the IRS ever investigates. That might actually work in your favor if you do decide to have a direct conversation about reclassification.

I feel your pain! I was doing the same thing until I learned transcripts don't update daily. Like others said, Friday mornings are when most updates happen, but it's not guaranteed every week. The IRS processes returns in waves, so some people wait weeks between updates. Save yourself the stress and check once a week max - your mental health will thank you! 😅

Same here! I was checking multiple times daily and it was driving me nuts. The Friday morning update schedule makes total sense now. One thing I learned - the IRS also does some updates on Wednesday nights around midnight EST, but it's less common. Also worth noting that during peak tax season (Feb-April), the systems can be slower and updates might be delayed by a day or two. Setting a weekly reminder for Saturday morning to check has been a game changer for my sanity! 🤯

One important aspect that hasn't been mentioned yet is the potential for double taxation and how to avoid it. Since you're Hong Kong-based, you'll likely need to report your US Amazon income on your Hong Kong tax return as well. Hong Kong operates on a territorial tax system, so if your business operations are conducted from Hong Kong (sourcing, management, etc.), you may be subject to Hong Kong profits tax on the same income that's being taxed in the US. To avoid double taxation, you can typically claim a foreign tax credit in Hong Kong for taxes paid to the US. However, the mechanics of this depend on your specific business structure and how you characterize the income in each jurisdiction. Also, consider the Branch Profits Tax if you operate through a US branch rather than a subsidiary. Non-resident aliens engaged in US trade or business through a branch may be subject to an additional 30% branch profits tax on earnings that aren't reinvested in the US business. I'd strongly recommend consulting with tax professionals in both jurisdictions before making your final structure decision. The initial setup cost is usually much less than the potential penalties and complications from getting it wrong.

As someone who went through this exact process last year from Hong Kong, I can share some practical insights that might help clarify things. The key decision point is really about your risk tolerance and compliance complexity. Here's what I learned: **Structure Decision:** I ended up forming a US LLC (single-member, electing disregarded entity status) rather than using a Hong Kong company. This simplified my US tax filing significantly - I file Form 1040-NR as an individual rather than dealing with corporate forms like 1120-F. The liability protection was worth the extra complexity. **Nexus Reality:** Don't get too caught up in where you "manage" the business. The moment your products sit in Amazon warehouses, you have US nexus. I tried arguing that my business was managed from Hong Kong, but my tax advisor quickly shut that down - physical inventory presence trumps management location. **State Tax Strategy:** Focus on the big states first. California, Texas, Florida, and New York will likely be where most of your inventory ends up. Register proactively in these states rather than waiting for notices. Amazon's sales tax collection helps, but you still need to handle income tax registrations. **Practical Timeline:** Get your EIN first (you can apply online as a foreign person), then set up your business bank account, THEN start selling. Trying to sort out the tax structure after you're already generating income is much more complicated. The Hong Kong side is actually simpler than the US side - just make sure you're claiming foreign tax credits properly to avoid double taxation. Happy to answer specific questions about the process!