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One thing nobody mentioned - check your transcript if you can access it online! The WMR tool is notoriously unreliable especially for PATH Act returns. My transcript showed codes 571/570 followed by 571/768/766 days before WMR updated. My DDD ended up being the cycle date + 6 days even though WMR still said processing.
Those transcript codes are so confusing tho. What do all those numbers even mean?
My theory is the IRS intentionally gives vague info about PATH Act refunds to prevent people from calling all at once. I've gotten EITC for 5 years straight and every year is different. Last year my refund hit my acct on Feb 24th, the year before it was March 10th. Both times I filed in January. š¤·āāļø Just have to be patient even though it sucks when you need the money.
In case this helps anyone else, here's exactly how I entered my Morgan Stanley 1099-B in FreeTaxUSA: 1. Go to the Income section 2. Select Investment Income 3. Choose "Capital Gains and Losses (Schedule D)" 4. Enter each section separately: - Covered Short Term (Box A on your MS form) - Covered Long Term (Box D on your MS form) - Non-covered Long Term (Box E on your MS form) Don't use the summary totals - enter each section's details separately. This matches what MS reports to the IRS.
Thanks for this breakdown! Quick question - do you know if I need to attach any extra forms or documentation about the non-covered securities when I file? My accountant friend mentioned something about this but wasn't sure.
You don't need to attach any additional forms when e-filing, but you should definitely keep documentation of your cost basis for the non-covered securities in your personal records. The main difference is that for covered securities, the IRS already has the cost basis information reported by Morgan Stanley. For non-covered securities, the IRS doesn't receive basis information, so the burden of proof is on you if you're ever audited. Keep purchase confirmations, inheritance documentation, or whatever shows how you determined your basis for at least 7 years after filing.
I had a similar issue with my 1099-B from Fidelity. The FreeTaxUSA mobile version makes this extra confusing! If you're on mobile, try switching to desktop view - the investment sections are much clearer there.
The mobile interface is terrible for investment stuff! I switched to desktop and everything made so much more sense. They really need to fix that.
One thing to consider - check if you closed out ALL positions before the year ended. If you rebought some positions in December that triggered wash sales but didn't sell them again before year end, those disallowed losses get carried over to the next year as part of your basis. I had a similar issue ($18K in wash sales) and found out I was holding positions on December 31st that had disallowed losses attached to them. A CPA probably can't help much with the current year taxes, but they might help you track which losses are deferred to next year. Also, were you trading in multiple accounts? That's another common way people get surprised by wash sales - selling at a loss in one account while buying in another (like a retirement account) within 30 days.
I think that's exactly what happened actually. I sold a bunch of stuff at a loss in early December, then bought back similar positions a couple weeks later thinking I'd start fresh in the new year. Never sold those December purchases so I'm guessing those losses are basically stuck in the cost basis now?
Yes, that's exactly what happened. The losses from your early December sales got disallowed when you repurchased similar positions a couple weeks later. Since you didn't sell those new positions before year-end, the disallowed losses are now part of your cost basis in those new positions. Those losses aren't gone - they're essentially deferred until you sell those positions (without repurchasing again within 30 days). So when you eventually sell those positions in the current year, you'll recognize those losses on next year's tax return. Unfortunately, this doesn't help your immediate tax situation, but at least the tax benefit isn't permanently lost.
Have you thought about trying to sell some assets at a gain to balance out some of your income now? Might offset some of the tax hit.
Someone I know tried the IRA-LLC structure for a different business (not blogging) and ran into major issues. The Self-Directed IRA custodian charged insane fees, and when the business generated over $1,000 in UBTI, they had to file Form 990-T which was a nightmare without professional help. Plus, their IRA had to pay the business fairly if they wanted to be involved personally. They ended up paying themselves a "fair market salary" from the IRA-owned LLC, which means that money was essentially taxed anyway (defeating some of the purpose), plus they had extra compliance costs. For a blog specifically, seems like WAY more headache than benefit unless you're planning to generate massive profits without personal involvement.
Did your friend have to completely dissolve the LLC eventually or were they able to make it work? I'm trying to understand if this is simply complex but doable vs actually impractical for most people.
They didn't dissolve it, but they had to restructure everything. They created a management company outside the IRA that handled all operations, then the IRA-LLC just became a passive investor in certain aspects of the business. Made the whole setup way more complicated and expensive than just running a regular business. The fees were also eye-opening - about $1,500 in annual custodian fees, plus tax preparation costs for the LLC itself and Form 990-T filings. For a blog, unless you're making serious money (like $50k+ annually), the compliance and administrative costs would probably eat most of your profits.
Just to add another consideration - what about SEO expenses and content creation costs? If the blog is in your IRA, you can't personally pay for things like hosting, domain registration, SEO tools, etc. All expenses MUST come from IRA funds. And if your blog needs capital for growth (better design, hiring writers, marketing), you're limited to what's in your IRA. You can't just add personal funds whenever needed without doing a formal IRA contribution (with all the normal limits).
That's such a good point. I didn't even think about the practical aspects of running the business. Would using personal credit cards for blog expenses count as a prohibited transaction too?
Amara Okafor
Don't forget about the AICPA resources if you're a student member! They have a Tax Section with amazing practice guides that break down complex areas of tax. Not cheap if you're paying full price, but student rates are reasonable. Also, Surgent CPA Review has a pretty good tax section in their materials that explains forms in the context of solving problems, which I found helpful for learning when and how to use each form.
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CosmicCommander
ā¢Are there any free or low-cost AICPA resources that non-members can access? I'm still early in my accounting program and not ready to commit to the membership fees yet.
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Amara Okafor
ā¢Yes, the AICPA has some free resources even for non-members. Check out their website section called "For the Public" which has some basic tax guides. They occasionally offer free webinars too - just need to register for an account. For really low-cost options while you're still a student, look into your school's library resources. Many university libraries have subscriptions to tax research databases like RIA Checkpoint or CCH IntelliConnect that would normally cost thousands. You can use those for free while you're a student.
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Giovanni Colombo
Honestly the best way I learned was by volunteering with VITA (Volunteer Income Tax Assistance). You get free training on forms, hands-on experience preparing real returns, and IRS certification. Plus it looks great on your resume while you're still a student! Sign up starts in the fall for the next tax season. They'll train you on all the common forms and when to use them. It's way more practical than just reading about this stuff.
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Fatima Al-Qasimi
ā¢I'm considering VITA, but worried it might be too basic for CPA prep. Don't they mostly just deal with simple returns? I'm trying to learn about more complex scenarios like business returns, trusts, etc.
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