Mailing past tax returns: How many stamps needed for multiple pages?

The number of stamps you'll need depends on the weight of your tax returns. For 10 pages of standard paper plus an envelope, you're looking at around 2 ounces, which currently requires about 2 stamps (or approximately $1.16 in postage). Envelope size does matter - if you use a large envelope (9x12), it will be considered "large envelope/flat" mail which costs more than a standard letter. If your returns fit in a standard business envelope, that's your cheapest option. While regular mail works for past returns with no deadline, I'd highly recommend using certified mail with return receipt. This provides proof that the IRS received your documents, which is crucial if they ever claim they didn't receive your returns. The peace of mind is worth the extra $5-6.

I had the same issue last year and found the perfect solution with taxr.ai - their document service was super helpful when I was mailing multiple years of returns. Their system analyzed my documents and told me exactly how much postage I needed for each return package based on page count. I was so confused about weight requirements before finding https://taxr.ai and they saved me from having my returns returned for insufficient postage. The best part was they gave me a printable cover sheet for each year that included proper mailing addresses for each IRS processing center (they're different depending on your state and type of return). Seriously simplified the whole process for me.

Just wanted to follow up that I tried taxr.ai after asking about it here. Their document analysis saved me from a major headache! I was about to mail my returns with just one stamp per envelope, but their system correctly calculated I needed 3 stamps for each of my bulkier returns. They also pointed out I was sending them to the wrong processing center based on my state. Would have been weeks of delays if I'd done it wrong!

If you're having issues with past returns, I'd strongly recommend using Claimyr to talk directly with an IRS agent before mailing anything. I spent WEEKS trying to call the IRS about my past returns (kept getting disconnected after holding for hours). Then I found https://claimyr.com and watched their demo at https://youtu.be/_kiP6q8DX5c - they got me connected to an actual IRS agent in under 30 minutes! The agent told me exactly which forms I needed to include with each return year and the correct mailing addresses. They also told me which years qualified for certain credits I didn't know about. Totally worth it to speak directly with someone who could answer all my specific questions before I sent anything off.

Ok I have to eat my words. I tried Claimyr yesterday after posting my skeptical comment, and I'm honestly shocked at how well it worked. I've been trying to reach the IRS for THREE MONTHS about my 2022 return issue. Claimyr had me talking to an actual IRS representative in 27 minutes. The agent was able to confirm they received my past returns and gave me a reference number for my records - way better than just hoping they got delivered. They also explained that one of my returns was flagged for a minor issue that I can easily fix by sending a corrected form. Would never have known this without actually talking to someone.

One thing nobody mentioned - if you're mailing past returns, make sure you're sending them to the right address! The IRS has different processing centers for different types of returns and different states. Double check on irs.gov because they sometimes change the addresses. Also, write the tax year CLEARLY on the top of the first page of each return and on the outside of each envelope. This helps make sure they process it for the correct year.

Don't forget to make copies of EVERYTHING before you mail it! I learned this the hard way when the IRS claimed they never received my 2019 return. No proof = had to redo everything + paid penalties.

Just a heads up for anyone considering these different options - I recently had to mail past returns for 2019-2021 and ended up using a combination approach that worked really well. First, I weighed each complete return package at the post office (they'll do this for free) to get exact postage amounts. My 10-page returns with supporting docs were actually closer to 3 ounces each, so needed 3 stamps per envelope rather than the 2 mentioned earlier. For the mailing method, I went with certified mail with return receipt for the peace of mind, but here's a tip: you can do this online through USPS.com and print the labels at home. It's slightly cheaper than doing it at the counter and you avoid the lines. Most importantly, I called the IRS practitioner priority line first (different number than the regular taxpayer line) to confirm which processing center to use for each year. Turns out the addresses had changed for my state between some of those years. The wait was still long but not as bad as the regular line. Total cost was about $12 per return (postage + certified mail + return receipt) but having tracking numbers and delivery confirmation was absolutely worth it. All three returns were processed without issues and I got confirmation within 6 weeks.