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Have you looked at H&R Block's free version? I think they handle some investment income for free, but there might be limits. Worth checking out.
Thanks for suggesting H&R Block. I actually tried their free version first before TurboTax, but they also wanted me to upgrade as soon as I entered my 1099-DIV information. Seems like most of the big companies use investments as a trigger for their premium versions.
That's frustrating! These companies are really aggressive with their upselling. Maybe try starting at the IRS Free File page (https://www.irs.gov/filing/free-file-do-your-federal-taxes-for-free) instead of going directly to the tax prep sites. Sometimes the versions you access through the IRS have fewer restrictions.
Slightly off-topic but if you're making so little in dividends and trading profits, maybe look into tax-advantaged accounts like Roth IRA for your investments? Then you wouldn't have to report those dividends or gains at all!
One option nobody has mentioned yet is that many credit unions and community organizations offer free tax prep through VITA (Volunteer Income Tax Assistance) programs. The income limit for these is typically higher than the Free File programs - often around $60k for individuals or $120k for joint filers. Check with your local credit union, library, or community center. The volunteers are IRS-certified and it's completely free.
That's good to know about VITA! Unfortunately with my income at $78,500 I'd still be above the threshold you mentioned. Are there any other community programs with higher income limits?
You're right that at $78,500 you'd be above the standard VITA threshold. Some regions have expanded programs with higher limits, but they're not common. At your income level, your most cost-effective option is probably still using a budget tax preparer like FreeTaxUSA, TaxSlayer, or Cash App Taxes. Even though they're not free for you, they're much cheaper than the premium services and offer essentially the same functionality for most straightforward tax situations.
Has anyone tried Cash App Taxes? I heard they offer completely free federal AND state filing with no income limits. I'm nervous about using something linked to a payment app though.
I used Cash App Taxes (formerly Credit Karma Tax) last year and it worked fine for me. Completely free for both federal and state with no income restrictions. The interface isn't as polished as TurboTax but it gets the job done. Just make sure your tax situation isn't too complex - they don't support some more obscure forms and situations.
One thing nobody's mentioned - if your alimony agreement was finalized AFTER 2019, alimony shouldn't be taxable income to you at all. The Tax Cuts and Jobs Act changed the rules. Only alimony under agreements finalized before 2019 is taxable to the recipient and deductible by the payer. Worth checking before you worry about constructive receipt.
Thanks for raising this point! My divorce was finalized in 2017, so I'm still under the old rules where alimony is taxable income to me and deductible for my ex. That's why I need to figure out the correct year to report it.
Got it! Since you're under the pre-2019 rules, then yes, constructive receipt applies and the experts above are correct - it's 2023 income for you since you received and deposited the check in 2023, regardless of when the funds became available. Just make sure your ex is also treating it as a 2023 payment on their return to avoid any IRS matching issues.
For what it's worth, I'm a bookkeeper and we always use the date a check is received, not when it clears. Banks might have holding periods, but that doesn't change when the income is constructively received according to tax law. Your situation sounds straightforward - 2023 income.
Another option is to check if your investment app integrates directly with tax software. I use one of the major tax prep programs, and it can automatically import all my trading activity directly from several brokerages. Saves tons of time and reduces the chance of errors.
Which tax software do you use? I usually just use the free online ones but I'm willing to pay for something if it'll make this process easier.
I use TurboTax Premier which is specifically designed for investors. It's not the cheapest option, but it directly imports from most brokerages and handles all the stock transactions automatically. H&R Block's Deluxe + State is another good option that's a bit less expensive and also has import capabilities for many investment platforms. If you want a free option, FreeTaxUSA can handle investments too, but you might need to enter summary information manually rather than direct importing.
Dont forget that if your trades were all done on the same platform, you might be able to use the composite method for reporting. Basically instead of listing each trade, you can group them by category (short-term vs long-term) and just report the totals. Check box 3 on Form 8949 if you're going this route.
This is actually not quite right. The composite method doesn't exempt you from reporting - the IRS still needs to be able to match what's on your 1099-B. What you're thinking of is summary reporting which is only available if all your basis was reported to the IRS (covered securities).
Zachary Hughes
There are legitimate ways to legally not have to file taxes if your income is below certain thresholds. For 2025, if you're single and under 65, you don't need to file if your income is below $14,350. Different thresholds apply for other filing statuses.
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Mia Alvarez
ā¢This is true but dangerous advice without context. Even if you're under the threshold, you might still want to file if you had any taxes withheld from paychecks because that's the only way to get a refund of that money. Also, certain credits like the Earned Income Credit require filing to receive them.
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Carter Holmes
I work for a state tax agency (not the IRS) and I can tell you that "under the radar" is basically a myth these days. Between W-2s, 1099s, mortgage info, and banking data, the government has a pretty comprehensive picture of your financial situation whether you file or not. Not filing just means giving up control of your tax situation and potentially leaving money on the table.
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