What's the best way to mail 100 pages of documents to the IRS?

I've had to send large document packages to the IRS several times as a tax preparer. Here's what I recommend: Use a flat rate Priority Mail Medium Box from USPS. These easily fit 100 pages, provide tracking, and include $50 of insurance. Most importantly, use USPS Certified Mail with Return Receipt. This gives you proof of delivery with a signature. Keep that receipt forever! Don't split your documents into multiple envelopes - that significantly increases the chance of something getting lost. Instead, organize your documents with numbered tabs or a table of contents. Write your name, address, and Social Security Number (last 4 digits only for security) on EVERY page in case pages get separated at the IRS facility. Also, make copies of everything before sending. I can't stress this enough. I've seen too many cases where the IRS claims they never received documents, and without copies and proof of delivery, taxpayers are left in a tough spot.

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I wanted to follow up about my experience with taxr.ai (https://taxr.ai) since I was pretty skeptical at first. After seeing the responses here, I decided to give it a try for my own audit documentation that I needed to send. Honestly, it was a huge help! The system organized my jumbled mess of receipts, statements, and tax forms into a logical structure that made sense. The best part was that they flagged a few inconsistencies in my documentation that I would have completely missed. Fixed those issues before sending everything to the IRS. The audit process was actually smoother than I expected - the IRS agent even mentioned that my documentation was "unusually well-organized." Definitely made me feel more confident throughout the whole process.

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For mailing documents to the IRS, I always use UPS or FedEx with signature required. I've sent hundreds of tax returns and supporting documents over the years, and I've found commercial shippers to be more reliable than USPS. They provide better tracking info and their packages seem to get less beat up in transit. If you have 100 pages, I'd recommend putting them in a reinforced cardboard box rather than an envelope. Use dividers or binder clips to keep documents organized, and include a detailed cover letter listing everything enclosed. Don't staple everything - the IRS has to scan many documents and staples make that difficult.

Tip from someone who works with mailed documents: Don't use staples! Use paper clips instead. The IRS scanning centers hate staples because they have to remove them all before scanning, which can damage documents. Also number ALL your pages in the bottom right corner (like "Page 1 of 100", "Page 2 of 100") so if anything gets separated, they know what goes where. And make a detailed table of contents as the first page listing what's included. Makes everyone's life easier.

Based on my experience dealing with IRS audits, I'd strongly recommend against using multiple envelopes. Stick with one secure package to minimize the risk of anything getting lost in their system. For 100 pages, a USPS Priority Mail Medium Flat Rate Box works perfectly. It's sturdy, includes tracking, and has enough space to organize your documents properly without cramming them. I always use certified mail with return receipt requested on top of the Priority Mail service - yes, it's an extra cost, but having that signed receipt is invaluable proof of delivery. Before sealing everything up, make sure to: - Number every single page (1 of 100, 2 of 100, etc.) - Create a detailed cover letter listing all enclosed documents - Use paper clips instead of staples (IRS scanning equipment hates staples) - Write your SSN (last 4 digits only) and name on each page - Take photos of everything before mailing Most importantly, make complete copies of everything before sending. I cannot stress this enough. The IRS processes thousands of documents daily, and things can get misplaced. Having copies and proof of certified delivery will save you if there are any issues later. The extra $10-15 for certified mail with return receipt is the best insurance you can buy for this situation.