If all else fails and the payment does get rejected, make sure you immediately make a payment through IRS Direct Pay online using a debit card or electronic funds withdrawal. That way you minimize the time between the rejected payment and the new one.

I'm glad to see you got this sorted out with your credit union! For anyone else who might face this situation, I wanted to add that you can also check the status of your scheduled payment on the IRS website. If you go to IRS.gov and look for "View Your Account Information" or "Get Transcript," you can often see pending payments and their status. Also worth noting - if you do need to cancel a direct debit payment with the IRS, you generally need to do it at least 2 business days before the scheduled payment date. After that window, you'd need to work with your bank to stop the payment, which might involve fees. The silver lining in situations like this is that it's a good reminder to always verify banking information twice when setting up any automatic payments, not just taxes. I've learned to keep a physical copy of a voided check handy specifically for these situations.

Has anyone successfully e-filed in this situation? I'm wondering if reporting partial 1099 income that belongs to someone else's SSN might cause the e-file to be rejected, or if I need to file by mail with attachments explaining the situation.

I'm dealing with a very similar situation right now with my Herbalife business during my divorce proceedings. What really helped me was creating a detailed spreadsheet showing exactly how we split the work and expenses throughout the year - things like who attended training events, who maintained customer relationships, who paid for inventory, etc. This documentation became crucial when determining our income split percentage. We ended up with a 65/35 split rather than 50/50 because I handled most of the customer service and product orders. My tax preparer said having this level of detail would be invaluable if the IRS ever questioned our separate filings. One thing I'd add - make sure you coordinate with your spouse about who's claiming which business expenses. We almost double-claimed some training costs because we weren't communicating well during the separation. Document everything and keep copies of all receipts with notes about who actually paid for what.

One thing nobody's mentioned yet - if you're really in a bind financially, you might qualify for Currently Not Collectible status. It's basically where the IRS determines you can't afford to pay them right now due to your financial situation. Interest and penalties still accrue, but collections actions stop. You have to disclose all your financial info (income, expenses, assets) using Form 433-F, and they'll determine if your necessary living expenses leave you unable to pay. It's temporary - they'll review your situation periodically to see if your finances have improved.

Just a quick warning from personal experience - if you wait until February 2025 without making ANY arrangements with the IRS, you might start getting notices about tax liens or levies before then. The IRS typically starts sending notices about 45 days after your filing if you owe money, and they escalate from there. After about 6 months of non-payment and non-communication, they might file a Notice of Federal Tax Lien, which appears on your credit report and can really mess up your ability to get loans, credit cards, etc. If you go further without addressing it, they could potentially levy (take money from) your bank accounts or garnish wages.

13 Has anyone noticed if specific Vanguard funds tend to cause these delays? I have a mix of their ETFs and Admiral shares and wondering if I should expect this issue next year too.

8 I went through this exact situation with Vanguard two years ago. The key thing to understand is that Vanguard typically sends forms by January 31st for straightforward accounts, but if you have any international funds, REITs, or certain mutual funds that had income reclassifications, they're legally allowed to wait until March 15th. Given that you had $2,000 in dividends and significant stock sales, you should definitely receive both forms. I'd suggest calling Vanguard's tax support line directly - they can tell you immediately if your account qualifies for the extended deadline and provide an exact date when your forms will be available. Don't panic about the IRS - as long as you file by the deadline (even with an extension if needed), you'll be fine. The important thing is getting accurate numbers, not rushing to file with estimates that might be wrong.

Just to add another perspective - I'd be cautious about pulling money from retirement accounts to invest in a down market, even with capital losses to offset some taxes. Time in the market within tax-advantaged accounts is incredibly valuable. Once you pull money out of a 401k, you can't put it back in beyond the annual contribution limits ($23,000 for 2025, plus $7,500 catch-up if you're over 50). Instead of withdrawing, have you considered adjusting your 401k investments to take advantage of the down market? You could reallocate within the 401k to buy investments that are currently discounted.

Just to clarify something that might help with your planning - when you have capital losses, they first offset any capital gains you have in the same tax year. Only after that can you use up to $3,000 per year to offset ordinary income (like wages or 401k distributions). Any remaining losses carry forward to future years. So with your $6,700 in losses, if you had no capital gains this year, you could offset $3,000 of ordinary income this year and carry forward $3,700 to next year. This means if you did take a 401k distribution, only a small portion of the tax impact would be reduced by your losses. The 10% early withdrawal penalty is calculated separately and isn't reduced by capital losses at all. So on a $10,000 early withdrawal, you'd pay $1,000 in penalties plus ordinary income tax on the full $10,000 (minus up to $3,000 offset from your losses). Have you looked into whether your employer offers any other options like in-service distributions or if you qualify for any hardship withdrawal exceptions?