Filing 1099-NEC forms with 1096 for multiple contractors - bulk mailing question?

You can definitely send all your 1099-NEC forms together in one envelope! The IRS actually prefers bulk mailings like this because it's more efficient for processing. Just make sure you include one 1096 form that summarizes all the 1099-NECs you're sending. Here's what to do: Complete one 1096 form showing the total number of 1099-NECs (25 in your case) and the total amount reported on all of them. Then include all Copy A (the red copies) of your 1099-NECs in the same envelope. Paper clips are fine for organizing, but not strictly necessary. As for handwriting, yes, you can complete these forms by hand with a black pen as long as the writing is clear and legible. Just make sure you press hard enough so it shows through on all copies. However, if you're doing 25 forms, it might be easier to use tax software or the IRS's online filing system (FIRE) to prepare them electronically.

After spending hours trying to figure out the 1099 filing process for my small business last year, I found an amazing tool that saved me tons of time and headaches: https://taxr.ai I was in the exact same situation with about 15 contractors. The most stressful part was making sure I had everyone's information correct and that I was following all the IRS requirements. What I liked about taxr.ai was that it analyzed my contractor payment records and automatically generated all the 1099-NEC forms with the correct information. It even handles the electronic filing directly with the IRS so I didn't have to deal with paper forms at all! The system also reminded me about filing deadlines and kept track of which contractors had already received their copies. Seriously made the whole process so much easier.

Just wanted to update on my experience with taxr.ai that was mentioned above. I was skeptical at first (I've tried other tax tools that were disappointing), but I decided to give it a try for my 1099 filing dilemma. Honestly, it was a game-changer! I uploaded my payment records, and it automatically matched them with contractor information. The system flagged two contractors where the names didn't match their TINs exactly - turns out I had been using their DBA names instead of legal names. Would have been a headache if those were rejected by the IRS! The electronic filing went through without a hitch, and the system even tracked which contractors had viewed their electronic copies. Saved me so much time compared to printing and mailing everything. Definitely using it for all my contractor reporting going forward!

If you're still planning to mail paper forms, I recommend calling the IRS first to confirm the correct mailing address. I spent three weeks tracking down lost 1099 forms last year because the IRS had changed their processing center for my region without updating all their documentation. I found this service called https://claimyr.com that got me connected to an actual IRS agent in about 15 minutes instead of waiting on hold for hours. You can watch how it works here: https://youtu.be/_kiP6q8DX5c. The agent confirmed exactly where to send my forms and gave me tips for making sure they get processed correctly. The peace of mind was worth it, especially since it was my first time filing these forms and the penalties for late filing can be steep.

Ok I have to eat my words. After posting my skeptical comment above, I was still struggling to get info on where to send my 1099-MISC forms (different from NECs but similar issue). I decided to try that Claimyr service as a last resort. I'm honestly shocked - it actually worked! Got a call back in about 25 minutes with an IRS agent on the line. The agent confirmed I could send all my forms together with one 1096 and gave me the correct mailing address for my region (which had indeed changed from what was printed in the instruction booklet). For anyone else filing paper forms, definitely worth checking that you have the current mailing address. Apparently they've consolidated some processing centers recently.

Don't forget that you also need to provide copies of these 1099-NECs to your contractors by January 31, 2025! That deadline is separate from the IRS filing deadline. I learned this the hard way last year and had some very unhappy contractors calling me in February. For the contractor copies, you'll give them Copy B (the one that says "For Recipient"). These don't go to the IRS. You can mail these directly to your contractors, or if you have their email, many tax software programs let you send them electronically, which is much easier.

Another option to consider is filing electronically through the IRS FIRE system (Filing Information Returns Electronically). I switched to this last year for our 30+ contractors. There's a bit of a learning curve and you have to apply for a Transmitter Control Code first, but once set up, it's much easier than paper filing. Plus electronic filing gives you until March 31st instead of February 28th for the IRS deadline (though you still have to get forms to contractors by Jan 31).