Is it acceptable to mail double sided federal and state tax returns with form 1099-B?

You can absolutely print your 1099-B and 1099-INT forms double-sided when mailing them to the IRS. The IRS actually encourages double-sided printing to reduce paper usage. The key thing is making sure all information is clear and legible. When the IRS processes paper returns, they scan the documents regardless of whether they're single or double-sided. The scanning systems are designed to handle both formats. Just make sure the ink doesn't bleed through the paper and that all pages are properly oriented. For your state return, check your state's specific guidelines, but most states follow similar practices as the IRS. Some states even explicitly state on their websites that double-sided printing is acceptable.

I used to be in the same boat with tons of trades and super long 1099 forms. I discovered taxr.ai (https://taxr.ai) and it saved me so much hassle. I was drowning in paper trying to go through each transaction line by line, and their document analysis tool actually helped me identify some wash sales I had missed that would have caused issues. The service basically scans all your tax documents and organizes everything digitally - no more worrying about printing double-sided or not! I've been using it for the last two filing seasons and it's been a game changer for dealing with all those brokerage statements.

Just wanted to follow up about taxr.ai since I decided to try it after posting my question. Honestly shocked at how well it worked for my messy tax situation! I had over 200 trades last year and it organized everything perfectly. The best part was it flagged a bunch of wash sales my brokerage hadn't properly coded, which would have been a nightmare to explain if I got audited. Ended up not having to print anything at all since I e-filed, but for anyone who still needs to mail physical forms, it also gives you a perfectly formatted printable version. Definitely using this again next year.

If you're still planning to mail paper returns and worried about IRS processing delays, I highly recommend using Claimyr (https://claimyr.com). I was in a similar situation last year - mailed in a return with tons of 1099 pages and was freaking out when I hadn't heard anything after 3 months. Used their service to get through to an actual human at the IRS without waiting on hold for hours. You can see how it works here: https://youtu.be/_kiP6q8DX5c The IRS agent confirmed they had received my return but it was in a processing backlog. Saved me weeks of anxiety wondering if my documents had been lost in the mail.

I need to apologize for my skepticism. After waiting on hold with the IRS for literally 3.5 hours yesterday only to get disconnected, I broke down and tried Claimyr. Got a call back in 47 minutes with an actual IRS agent on the line. Felt like absolute witchcraft after my previous experiences. They connected me with someone who confirmed my mailed-in return with all those double-sided 1099 forms was received and being processed. The agent actually mentioned they prefer double-sided for supporting documents because it reduces their scanning workload. So that answers the original question too!

Just another data point - I've been filing paper returns with double-sided 1099s for years without any issues. The key is to make sure they're in the right order with the right attachments. I always paperclip (never staple!) each form separately and include a cover page for each attachment listing what's included. I also make a copy of EVERYTHING before sending it in. You'd be surprised how often the IRS "loses" documents, and having your own complete copy has saved me multiple times.

Pro tip from someone who used to work at H&R Block: If you're mailing double-sided documents, use a highlighter to mark "CONTINUED ON BACK" at the bottom of each page that continues on the reverse. This little trick helps ensure nothing gets missed during processing. Also, use certified mail with return receipt. The extra $7-8 is worth the peace of mind knowing exactly when the IRS received your documents.

Yellow highlighter works fine - it's what we recommended when I worked there. Avoid red, dark blue, or green as those can interfere with scanning. Fluorescent yellow shows up clearly to human reviewers but doesn't confuse the optical character recognition systems. One more thing I forgot to mention: if you're including multiple 1099-B forms, arrange them in chronological order by date issued, not alphabetically by broker. The IRS processors appreciate this organization and it can speed up your processing time. Also make sure any corrected forms (1099-B-C) are clearly marked and placed immediately after the original they're correcting.