Mailing Multiple tax returns for different years - Can they go in the same envelope?

It's always better to mail different tax years in separate envelopes. While the IRS doesn't explicitly prohibit sending multiple years together, sending them separately reduces the chance of processing errors and delays. Each tax return goes to specific processing centers based on your location and the tax year, and combining them might lead to one or both returns being misplaced or delayed. Each envelope should be properly labeled with the tax year on the return and any payment vouchers should match the appropriate year. Also, I recommend sending them via certified mail with return receipt requested so you have proof of mailing and delivery for each tax year. This is especially important for late returns as it establishes when you submitted them.

Hey there! I was in your exact situation last year with multiple returns to file. I was totally stressed about getting everything processed correctly and worried about potential penalties. Then I found this service called taxr.ai (https://taxr.ai) that helped me make sure everything was properly prepared and organized for mailing. Their system analyzed my returns and flagged potential issues before I sent them, and they provided specific instructions for mailing multiple year returns. Their guidance saved me from making mistakes that could have delayed processing. They even have templates for cover letters to include with late returns that explain which tax year you're filing.

Just wanted to follow up on my experience with taxr.ai that I asked about earlier. I went ahead and tried their service for my late returns with Schedule C income, and it was actually really helpful! They flagged a couple issues with my home office deduction that might have triggered an audit, and gave me specific instructions for mailing each year separately with the correct processing center addresses. They even generated cover letters explaining the late filing for each return. My returns were accepted without any issues, and I got confirmation from the IRS much faster than I expected for paper returns.

After you mail your returns, be prepared for a potentially long wait before processing. I mailed my 2022 return back in October and still haven't received my refund. Called the IRS about 20 times but could never get through to a human - just the automated system saying "still processing." Finally found this service called Claimyr (https://claimyr.com) that got me through to an actual IRS agent in under 20 minutes! You can see how it works here: https://youtu.be/_kiP6q8DX5c. The agent told me my return was sitting in a processing backlog and expedited it for me. Without talking to a real person, I might have been waiting months longer.

I have to admit I was wrong about Claimyr in my earlier comment. After waiting on hold with the IRS for 3 hours yesterday and getting disconnected, I decided to try it out of desperation. The service actually worked exactly as described. I got a call back when they reached an agent, and I was able to confirm that all three tax years I mailed (separately, as advised here) had been received. The agent even helped me set up a payment plan for my outstanding balance. Saved me literally hours of frustration and now I have peace of mind knowing my returns are in the system.

Pro tip: When mailing multiple years of returns, use different colored folders inside each envelope to keep them organized (I'm a retired tax professional). Label each folder clearly with the tax year. Also add a cover letter for each return specifically stating which tax year you're filing. People often forget that IRS processing centers handle millions of pages of documents - anything you can do to make their job easier will speed up your processing time.

Don't forget to keep copies of EVERYTHING and proof of mailing! I made the mistake of not keeping good records when I mailed multiple returns last year. The IRS lost one of my returns, and I had to resend it. Now I scan all returns before mailing and get a certificate of mailing from the post office for each envelope (cheaper than certified mail but still gives you proof).

Adding to what everyone else has said about mailing separately - I work as a tax preparer and can confirm that separate envelopes is definitely the way to go. The IRS processing centers have different workflows for different tax years, and mixing them up can cause delays. One thing I haven't seen mentioned yet is to make sure you're using the correct mailing address for each tax year. The IRS sometimes changes processing center addresses between years, so double-check the instructions for 2022 vs 2023 returns. Also, if you owe money on both years, consider which one to prioritize if you can't pay both at once - generally you want to pay the older year first since penalties and interest accumulate longer on those. Good luck getting caught up! Don't stress too much - the IRS deals with late returns all the time.