Another thing to consider with RSUs - if you hold the shares after vesting and sell within a year, any gain/loss is short-term capital gain/loss. If you hold more than a year after vesting, then it becomes long-term capital gain/loss. This matters because short-term capital gains are taxed at your ordinary income rate, while long-term capital gains get the preferential tax rates (0%, 15%, or 20% depending on your income level). So while your capital loss carryover can offset either type of gain, it might be strategically better to use it against short-term gains if you have both.

This is a really comprehensive discussion! I wanted to add one more consideration that might be helpful for OP and others - timing your RSU sales strategically with your capital loss carryover. Since you have $55k in capital loss carryover, you might want to consider holding onto those RSU shares after they vest and selling them strategically over multiple years. Here's why: if the shares appreciate and you sell them all at once for a big gain, you'll use up your entire loss carryover in one year. But if you spread the sales over several years, you can also take advantage of the $3k annual deduction against ordinary income each year. For example, if you sell $10k worth of gains each year, you'd offset that with your carryover losses AND still get to deduct $3k against your regular income each year. This way you're maximizing the tax benefit of those losses. Of course, this assumes you're comfortable with the investment risk of holding the shares longer. Just something to consider when planning your RSU strategy!

7 What about tracking expenses for content creation? For example, if I bought a special camera or lighting equipment specifically for creating content, can I deduct that? How do I prove it's for business and not personal use?

This is exactly the kind of situation where it's worth getting clarity early! I went through something similar when I started my freelance writing side hustle. Even though $75 seems small, reporting it correctly from the start establishes good habits and keeps you compliant. One thing I learned is to start keeping track of ALL your business-related expenses now, even the small ones. Things like software subscriptions, web hosting, even a portion of your phone bill if you use it for business communications. These deductions can add up and offset your income. Also, consider opening a separate bank account for your content creation income and expenses. It makes record-keeping much easier and looks more professional if you ever get audited. Even a simple checking account works - you don't need anything fancy when you're just starting out. The key is treating this like a real business from day one, even if it's small. That mindset will serve you well as you grow!

pending since OCTOBER?? nah fam thats wild 😤

I've been dealing with similar issues and what finally worked for me was getting my account transcript and looking for the specific transaction codes. The 570 freeze code is common but there are others like 971, 810, etc. Each one requires different steps to resolve. If your advocate isn't responding, try calling the Taxpayer Advocate Service directly at 877-777-4778 and ask for a case status update. You can also try the IRS Practitioner Priority Service if you have a tax professional helping you. Don't give up - sometimes it takes multiple calls but eventually you'll get someone who can actually help move things along.

Something similar happened to me last year. I ended up contacting the HR department at my previous employer. Since they were the plan sponsor, they had access to all the plan documents and were able to request a duplicate 1099-R on my behalf. Might be worth giving that a try!

I work in tax compliance and see this issue frequently. Here's what I'd recommend in order of priority: 1. **Contact your old employer's HR/benefits department first** - This is often the fastest solution. As the plan sponsor, they maintain administrative access and can request duplicate tax documents even after you've left the company. 2. **Call Fidelity's dedicated tax document line at 1-800-544-4774** - When prompted for account info, immediately say "tax documents for closed account" or "representative." They're legally required to provide your 1099-R regardless of account status. 3. **Visit a Fidelity branch in person** - Bring your driver's license and be prepared to provide your SSN, previous address, and approximate account balance. This often cuts through the phone system issues. Important note: Even though this was a direct rollover, you still need to report it on your tax return (Form 1040). The 1099-R should show distribution code "G" in Box 7, which indicates it's a non-taxable direct rollover. The IRS receives a copy of this form and will expect to see it reported, even though it won't increase your tax liability. Don't panic about the timing - you have until the tax filing deadline to get this sorted out, and Fidelity is actually already late since 1099-Rs were due by January 31st.

Omg I feel your pain!!! I had this happen and my check got sent to my old address even though I SWEAR I updated everything correctly!!! 😡 Had to wait another 6 weeks for them to reissue after the first check was returned. Make absolutely sure your current address is on file with the IRS RIGHT NOW!!! Don't just assume they have it right - double check on the IRS website by creating an account if you don't already have one. Trust me, you don't want to add another month to this process!!!

This exact thing happened to me two years ago and I was SO stressed! Here's what I learned from the experience: The good news is your money isn't lost - the IRS has pretty solid procedures for this. When TurboTax (or any tax software) sends your refund to the wrong account and it gets rejected, the bank automatically returns it to the Treasury within 1-2 business days. The IRS then converts it to a paper check without you having to do anything. My timeline was: rejection happened on a Tuesday, IRS processed the return on Friday (showed up on my transcript), and I got the paper check the following Wednesday - so about 8 business days total. Pro tip: Check your IRS transcript online to track the progress. You'll see transaction codes that show when the rejection happened and when the new check was issued. It really helped calm my nerves to see the process actually working! And definitely don't call the IRS unless it's been over a month - their phone lines are swamped and this process is completely automated. Save yourself the headache! 😊