How long after you get a W-2 should you file your tax return?

So if I worked two regular jobs with W-2s but also did some freelancing where I was paid directly (no tax forms from them), should I still wait until Feb 15 or just go ahead and file since I know what I made from the freelancing?

If you received direct payments from freelancing where no tax forms were issued, you should still report that income, but you don't need to wait for any documents for it. For freelance income without tax forms, you'll need to track that income yourself and report it on Schedule C. Just make absolutely sure you have all your W-2s in hand before filing, and any 1099s if you expect them from other sources like banks, investment accounts, etc.

Does it work with digital versions of W-2s? My employer only offers electronic W-2s and I'm never sure if I downloaded everything correctly.

I'm kinda skeptical about uploading my tax docs to a random website... is it actually secure? What about privacy?

Yes, it works perfectly with digital W-2s! I use it with both PDFs from my employer's portal and even screenshots from my phone. It can extract the data regardless of the format. As for security concerns, they use bank-level encryption for all uploads and processing. Nothing is stored permanently unless you specifically save it to your account. They also have a pretty detailed privacy policy explaining how your information is handled - basically, they don't sell or share any of your data with third parties. I was hesitant at first too, but they've been really reliable.

How does this actually work? Do they have some special connection to the IRS or something? Seems too good to be true that they can get through when nobody else can.

Yeah right, no way this works. The IRS is deliberately understaffed to make it impossible to get through. I've tried calling over 50 times last year and never got a human. Some website can't magically fix a broken system.

There's no special connection to the IRS - they just have an automated system that handles the frustrating parts of the call process for you. It continually calls and navigates through all the IRS prompts, then stays on hold (sometimes for hours) so you don't have to. When an actual human agent picks up, that's when they call you and connect you directly. The reason most people can't get through isn't that it's impossible - it's that nobody has time to stay on hold for 2+ hours during business hours. Their system just does the waiting for you, which is why it feels like magic but is actually just clever automation. There's no guarantee on exact timing since it depends on IRS call volume, but it's significantly better than the DIY approach.

Did changing your filing status to married filing jointly end up getting you a bigger refund? I got married last October and I'm trying to figure out if we should file separately or together.

In my case, filing jointly definitely resulted in a larger refund. We saved about $2,100 compared to what we would have paid filing separately. The benefits really depend on your specific income situations though. Generally, filing jointly benefits couples where one person earns significantly more than the other. If you both have similar incomes in higher tax brackets, sometimes filing separately works out better. Tax software can usually help you compare both scenarios to see which gives you the better outcome.

I filed on February 2nd last year and got my direct deposit exactly 9 days later. The IRS says 21 days is the standard, but direct deposits are usually much faster if you e-file and there are no issues with your return.