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Don't sleep on OLT.com (OnLine Taxes). It's under $50 for federal + state, and handles investment sales, 1099s, etc. Interface isn't fancy but gets the job done. Been using it for 5 years with similar tax situation to yours.
Have you used it for reporting inherited stocks? That's the part that's tripping me up with my grandma's investments. Need to make sure I get the cost basis right.
Yes, I've used it for inherited stocks. It handles the stepped-up basis correctly - there's a specific section where you can indicate the shares were inherited and enter the fair market value on the date of death as your basis. It also has a surprisingly helpful help section that explains the inheritance rules clearly. Way better than some of the more expensive options I tried previously that made this unnecessarily complicated.
anybody have thoughts on TaxHawk? its basically freetaxusa with a different name... might work for you if youre having specific issues with the freetaxusa interface but still want the same basic system?
Something to be aware of: if the financial institution already reported the transaction to the IRS as a taxable event using a 1099-R, they are required to issue a corrected 1099-R (often called a 1099-R with the "CORRECTED" box checked). Simply changing their internal paperwork doesn't fix the issue with the IRS. Also, for future reference for anyone inheriting annuities: always be extremely clear about requesting a "direct trustee-to-trustee transfer" not a "rollover" when moving inherited annuity funds. Get confirmation in writing before the transaction processes, and if possible, have the receiving institution initiate the transfer rather than the sending institution.
Is there a time limit on when a financial institution can issue a corrected 1099-R? My mom's situation happened almost 2 years ago and we're just now discovering the mistake.
There's technically no specific time limit for a financial institution to issue a corrected 1099-R. They can (and should) correct erroneous information even years later. For your situation with your mom, you generally have 3 years from the original filing deadline to file an amended return to correct mistakes. So even at 2 years out, you still have time to get this fixed. The financial institution may be resistant since it creates extra work for them, but they are obligated to provide accurate tax reporting. Be persistent and escalate to management if needed.
Has anyone successfully had the IRS waive penalties and interest in a situation like this? I got the financial institution to admit their error, but the IRS is still charging me penalties and interest on the "deficiency" even though they agree I don't owe the base tax anymore.
Yes, I had success getting penalties (but not all interest) waived by requesting penalty abatement due to reasonable cause. I explained that the error was made by the financial institution, not me, and provided their admission letter. The IRS has discretion here and often waives penalties when you can prove the error wasn't your fault.
Hey, I've been using Taxport Convey for years. For the validation errors you're getting, there should be a "Review Exceptions" button on the main dashboard. Click that, then look for "Chapter 3 Exceptions" in the dropdown. From there, you can batch update all similar errors with the correct exemption code. For dividend payments under Chapter 3, if the recipient has provided a valid W-8BEN or W-8BEN-E claiming treaty benefits but no TIN, you generally have a 90-day grace period where you can still apply the treaty rate. After that, you may need to default to 30% withholding unless they qualify for another exemption. Also, make sure you're using the correct country code in the system - sometimes Taxport Convey will flag TIN issues if the country code doesn't match what's on the W-8.
Thanks for the specific guidance on Taxport Convey! I found the "Review Exceptions" option and it shows all 42 errors in one place. If I implement the 90-day grace period approach, will I need to go back and amend these later if we don't receive the TINs within 90 days?
Yes, if you don't receive the TINs within the 90-day period and you've applied treaty rates, you would technically need to file amended returns using the higher withholding rate (typically 30% for Chapter 3). However, there's an exception for certain passive income, including some types of dividends, where you may be able to continue applying treaty rates if you have other sufficient documentation. I would recommend documenting all your follow-up attempts to obtain the TINs. If you can show reasonable efforts to obtain the information, it can help if there's ever an IRS review of your filings.
Just to add something useful - as someone who had to learn 1042/1042-S filing on the fly last year, I'd recommend downloading IRS Publication 515 and the 1042-S instructions. They're surprisingly helpful once you know what you're looking for. Specifically for your issue with Chapter 3 withholding, look at the section about "Withholding and Reporting Obligations" in Pub 515, around page 40-42. It outlines the scenarios where TINs are required vs. where you can proceed without them. The 1042-S instructions also have a table of exemption codes on page 25 that explains exactly when each one applies. Might save you some time vs. trying to piece it together from different websites.
Something similar happened to me in 2022 - I couldn't find a 1099-MISC from a small client but had reported all the income. I just wrote a little note explaining the situation and attached it to my return. Never heard anything about it, so I assume it was fine! But one thing to consider - the companies that issue 1099s are required to send them to you by January 31, and they also send copies to the IRS. So the IRS already has a copy of your 1099 in their system, even if you don't have yours. They mainly want to make sure the numbers match up.
Does the IRS actually check every single form against what they have on file? I thought they just randomly audit a small percentage of returns?
The IRS uses automated matching programs that compare what's reported on your tax return with the information they receive from employers, banks, and other institutions. It's not a manual process checking every form, but their systems will flag discrepancies. This automated matching happens for most returns, not just those selected for audit. So if the income on your missing 1099 doesn't match what you reported, you might receive a notice from the IRS later. That's why it's important to report the income accurately even if you don't have the form.
Ughhh I'm in the exact same boat! My tax software kept giving me errors when I tried to e-file so now I have to mail everything. Has anyone tried calling the company that issued the 1099 directly? My situation is with a 1099-NEC from a company I did freelance work for last summer but I think I threw out the form accidentally when moving in December...
Yes! Definitely call the company directly. Most businesses can easily generate a new copy of your 1099. I had this issue with a 1099-INT from my bank and they emailed me a PDF version within an hour of calling. Some companies even have portals where you can download your tax documents yourself.
Jessica Nolan
If you filed electronically through any major tax software (even if someone else prepared it for you), you might be able to access your returns that way. Ask your preparer which software they used. TurboTax, H&R Block, TaxAct, etc. all store your returns in your account. Also, check your email from around tax time in 2022 and 2023 - you might have received a confirmation email with a PDF copy of your return attached or a link to access it.
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Sophie Footman
β’Good idea about checking emails! I just did a search through my inbox for "tax return" and "1040" and found an email from April 2022 that has my 2021 return attached, but nothing for 2022 or 2023. I'm going to try reaching out to coworkers who might know what software our tax preparer used.
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Jessica Nolan
β’Glad that helped with at least one year! Another thing to try is looking at your bank statements from when you paid to have your taxes done. The charge might list the name of the tax software, not just the preparer's business name. Also, if you received tax refunds for those years, check your bank deposits around tax time - the deposit details sometimes include information about which service processed your return.
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Angelina Farar
Have you checked with your spouse? My husband and I had a similar situation, and it turned out he had the tax returns saved in a folder on his work computer that he had completely forgotten about. Also check any cloud storage you might use - Google Drive, Dropbox, OneDrive, etc. If all else fails, the IRS transcript option others mentioned is definitely the way to go. Just verify with your mortgage lender exactly what they need - some are fine with transcripts while others want the complete 1040 with all schedules.
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SebastiΓ‘n Stevens
β’This happened to me too! Found our returns in my husband's email (he had forwarded them to himself from his accountant and then completely forgot). Always check with your spouse first before going through the hassle of IRS requests.
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Sophie Footman
β’My wife and I have been searching everywhere! We looked through all our devices, cloud storage, and email accounts. I even found some older tax documents from 2020, but nothing for 2022 or 2023. I'm starting to think our tax preparer never actually gave us copies, which is frustrating. I've called our mortgage lender, and they confirmed they need the actual 1040 forms, not just transcripts. They need to verify some specific deductions that apparently don't show up on the transcript. Going to try the IRS Form 4506 route and see if I can get expedited processing.
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