I went through this exact same frustration last year! You're absolutely right that there's no free direct e-filing option on the IRS website for Form 7004. After trying multiple approaches, I ended up mailing it in with certified mail and it worked fine. One thing that helped me was calling my local IRS Taxpayer Assistance Center - they confirmed that mailed extensions are processed just as validly as e-filed ones. The key is getting it postmarked by the deadline, not necessarily received by then. For what it's worth, I budgeted about $50 for extension filing this year and found a couple of legitimate e-file providers in that range. It's annoying to pay for something that should be free, but the peace of mind from instant confirmation might be worth it depending on your situation. Just make sure whatever service you use is IRS-authorized - you can check the list on the IRS website.

I feel your pain on this! I went through the exact same frustration with our LLC last year. After hours of searching the IRS website, I finally accepted that there's just no free direct e-filing option for Form 7004 - it's really disappointing that such a simple extension form requires either paying a third party or dealing with paper filing. I ended up going the certified mail route and it worked out fine, but the lack of immediate confirmation was nerve-wracking. This year I'm planning to bite the bullet and pay for e-filing just for the peace of mind. It's frustrating that the IRS makes small businesses jump through these hoops when individual taxpayers get so many free filing options. One tip: if you do decide to mail it, make sure you're sending it to the correct processing center for your state - the addresses are different depending on where your business is located. I almost sent mine to the wrong place last year which would have been a disaster!

I think everyone is overthinking this! Just enter the info from the W2 and you're fine. The IRS only cares about who paid you and if the correct taxes were withheld. I've worked for like 5 different staffing agencies over the years and never had an issue. That checkbox in H&R Block is probably asking if you're self-employed. Since you got a W2, you're not self-employed, so don't check it. Simple as that!

I went through this exact same situation last year when I worked for a client through Kelly Services! You're absolutely right to treat Robert Half as your employer for all tax purposes since they issued your W2. The key thing to remember is that from the IRS perspective, you were an employee of Robert Half who happened to be assigned to work at their client's location. This is a completely normal and well-understood employment arrangement. For that checkbox you're seeing in H&R Block - if it's asking about self-employment status, definitely don't check it since you received a W2 (not a 1099). If it's asking something else and you're still unsure, you can always skip it for now and come back to it, or look for a help button that explains what that specific question is asking. Don't stress too much about it - staffing agency employment is super common and the tax software is designed to handle it properly!

Don't forget about FBAR filing requirements if your foreign accounts exceeded $10,000 combined at any point during the year! That's separate from your tax return and has huge penalties if missed. The deadline is April 15 with an automatic extension to October.

I just went through this exact situation last year and want to share what worked for me. You're absolutely right to be confused - foreign income reporting is one of the most complicated parts of US tax filing! For your foreign interest and dividends, you'll report them on Schedule B alongside your US income. Make sure to check the box indicating you have foreign accounts and specify the countries. The fact that you don't have 1099 forms doesn't matter - you still report the income based on your foreign bank statements. For the foreign capital gains, these go on Schedule D and Form 8949 just like US capital gains. You'll need to convert the foreign currency amounts to USD using the exchange rate from the date of sale. The key is Form 1116 for claiming your foreign tax credits. I'd strongly recommend filing separate Form 1116s for different income categories (passive income vs capital gains) as others mentioned - this typically maximizes your credit. One thing that really helped me was keeping detailed records of the foreign taxes paid with documentation from the foreign tax authorities. The IRS may ask for proof later, and having everything organized upfront saved me a lot of headaches. Also, double-check if you need to file FBAR (FinCEN Form 114) if your foreign account balances exceeded $10,000 at any point during the year. It's a separate filing requirement with serious penalties for non-compliance.

Make sure you're keeping track of your Form 8606 information year to year! This bit me hard last year. If you've been doing backdoor Roth conversions for multiple years, you need to have the previous year's Form 8606 values for line 14 (your basis). TaxAct won't automatically pull this information from your previous returns, even if you used TaxAct last year. Messed this up once and almost paid tax twice on $12,000!

I went through this exact same nightmare with TaxAct last year! The software's handling of backdoor Roth conversions is definitely not intuitive. Here's what finally worked for me: 1. Don't enter your 1099-R first - that just confuses the software 2. Go to Federal > Income > IRA, Pensions and Annuities and find the Form 8606 section 3. Answer "yes" to making nondeductible contributions to a traditional IRA 4. Enter your basis (the amount you contributed with after-tax dollars) 5. THEN enter your 1099-R information The key insight is that TaxAct needs to know about your nondeductible contributions before it processes the conversion. Once you do this correctly, only the small amount of earnings (like that $3 of interest you mentioned) should be taxable. Also, keep really good records of your Form 8606 from year to year - you'll need the basis information for future conversions. I learned this the hard way when I almost paid tax twice on a $6,000 conversion because I didn't carry forward my basis correctly. Hope this helps save you from the hours of frustration I went through!

This thread has been incredibly helpful! I'm in a similar situation with some Apple shares I've held since 2012. Based on all the advice here, I'm planning to donate about $25,000 worth directly to my church rather than selling first. One question I haven't seen addressed: if I'm planning multiple charitable donations this year (both cash and stock), should I bunch all my giving into one year to exceed the standard deduction threshold, or spread it out? My wife and I typically donate about $8,000 annually in cash, but with the stock donation we'd be at over $33,000 this year. Also, has anyone dealt with a situation where you want to donate to multiple charities but some can accept stocks and others can't? I'm wondering if it makes sense to use a donor-advised fund for everything or just for the organizations that can't handle direct stock transfers.

This is such valuable information! As someone new to stock donations, I'm wondering about the mechanics of actually selecting which specific shares to donate when you have multiple purchase dates. For example, if I bought SPY shares in 2010, 2015, and 2020, and I want to donate $10,000 worth, how do I ensure I'm donating the shares with the lowest cost basis to maximize the tax benefit? Also, does anyone know if there are any restrictions on donating shares that are part of a dividend reinvestment plan (DRIP)? I have some utility stocks where I've been automatically reinvesting dividends for years, so I have dozens of tiny purchase lots at different prices. Would this complicate the donation process, or can I still select the most advantageous shares to transfer? Finally, I'm curious about the timing of when to get the stock appraised for fair market value. Do I need to get a formal appraisal before initiating the transfer, or is using the average high/low price on the transfer date sufficient for tax purposes?