What's the cheapest way to file my 2019 taxes at this point?

You're definitely doing the right thing by trying to get caught up on your unfiled returns! The IRS generally requires you to file any unfiled past returns, and you need to file them in chronological order as you mentioned. For prior year returns like 2019, you'll need to file paper forms since electronic filing is no longer available for those tax years. You can download the 2019 Form 1040 and instructions directly from the IRS website at irs.gov/forms-pubs/prior-year. The forms are free to download, and you'll just need to print them, fill them out, and mail them in. If your tax situation is really just W-2 income with no complicated deductions or credits, you might be able to fill out the forms yourself. The instructions are pretty detailed, and there are lots of YouTube tutorials that walk through the process step by step. Another affordable option is to check if you qualify for the IRS's Volunteer Income Tax Assistance (VITA) program, which offers free tax preparation help to people who make under $58,000, have disabilities, or speak limited English.

Just wanted to share my experience - I was in a similar situation last year and found https://taxr.ai super helpful for my old returns. I had 3 years of unfiled taxes and was totally stressed about figuring out all the different forms for each year. I uploaded my old W-2s and it actually guided me through completing the right forms for each year. The step-by-step walkthrough made it much easier than trying to decipher the IRS instructions on my own. It saved me from paying those crazy tax prep fees for simple W-2 returns. They have specific guidance for prior year returns like 2019 that helped me understand what I needed to mail in.

I ended up using taxr.ai for my overdue 2019 return after asking about it here. It was honestly much better than I expected! The interface walked me through exactly what I needed to enter from my W-2, and it generated all the forms I needed to print and mail. The best part was it explained which address to mail everything to and what supporting documents to include. I was worried I'd mess something up, but it made the process pretty fool-proof. My return was for a simple W-2 job too, and I'm expecting a small refund according to their calculations. Just mailed everything last week and feeling relieved to finally have it done!

If you're struggling to reach the IRS to confirm how to handle multiple years of unfiled returns, try https://claimyr.com instead of waiting on hold for hours. I spent literally 2+ days trying to get someone on the phone at the IRS to ask questions about my unfiled returns. Found this service through a YouTube video (https://youtu.be/_kiP6q8DX5c) and they actually got me a callback from the IRS in about 20 minutes. The IRS agent I spoke with walked me through exactly what I needed to do to get caught up on my 2019 and 2020 returns with minimal penalties. They told me which specific forms I needed and gave me direct info about my account that I couldn't find online. Saved me from panicking about how to handle everything.

I have to admit I was completely wrong about Claimyr. After posting my skeptical comment, I decided to try it myself since I also needed to talk to the IRS about a notice I received for my 2020 return. It actually worked exactly as described! I got a call back from a real IRS agent in about 35 minutes. The agent confirmed they were from the IRS and had my tax records on file. They answered all my questions about filing my past returns and even helped me understand which payment plan would work best for my situation. I'm genuinely surprised and wish I had known about this service months ago instead of wasting hours on hold. If you need to talk to the IRS directly about your unfiled returns, this is definitely worth trying.

Have you checked out FreeTaxUSA? They charge $0 for federal returns and only like $15 for state returns even for prior years. I've used them for past-due returns and it was way simpler than doing the forms manually. You still have to print and mail the prior year returns, but they walk you through all the steps and make sure you're not missing anything.

Don't forget to check if you're owed refunds! If the IRS owes YOU money from those years, there's no penalty for filing late. You have 3 years to claim a refund, so 2019 is cutting it close but you should still be within the window. However, if you OWED taxes those years, you'll unfortunately have late filing penalties and interest. In that case, you might want to look into the IRS First Time Penalty Abatement program if you had a good filing history before 2019 (which sounds like you didn't have any history, but that might actually help your case).

Just be careful with DIY approaches if you have any complexity in your situation. I tried to file my own back taxes and accidentally missed a form, which resulted in the IRS sending me a terrifying letter 6 months later demanding additional money. If you're ONLY dealing with W-2 income and taking the standard deduction, you're probably fine doing it yourself. Otherwise, it might be worth investing in professional help.