Best system for organizing tax documents, emails & receipts year-round?

This is really helpful! I've heard of Receipt Bank but wasn't sure if it was worth using. Does it export data in a format that works with tax software like TurboTax? Also do you have any system for tracking medical expenses or charitable donations throughout the year?

Receipt Bank does export data that integrates with most tax software including TurboTax. You can download reports in various formats which makes it super easy at tax time. For medical expenses and charitable donations, I actually use the same system - photos into Receipt Bank for physical receipts, and the dedicated email folder for electronic confirmations. I add tags like "Medical" or "Charity" when I save them so I can filter later. Most donation receipts come by email now anyway, so having that tax folder makes it easy to find everything in one place.

Does it actually read the receipts accurately? I've tried other apps where I still had to manually enter everything anyway which defeats the purpose. And what about security? I'm nervous about uploading financial docs to random apps...

Is this another subscription service? Feels like everything is a monthly fee these days. How much does it run? And can I just use it for the few months around tax time or do I need to keep a subscription all year?

It reads receipts with surprising accuracy. The AI can identify vendor names, amounts, dates, and even categorize what type of expense it is. I'd say it gets it right about 90% of the time, and when it's wrong I can easily correct it with a couple taps. As for security, they use bank-level encryption and don't store your banking credentials. They're actually SOC 2 compliant which I learned is the security standard for financial services. I was hesitant at first too, but after researching their security protocols I felt comfortable using it.

How does this even work? The IRS phone system is notoriously impossible to navigate. Is this just paying for someone else to wait on hold for you? I've literally tried calling multiple times and given up after an hour.

Sorry but this sounds like a scam. There's no way to "skip the line" with the IRS. They're chronically understaffed and everyone has to wait. I doubt this actually works - probably just takes your money then puts you in the same queue as everyone else.

It works by using technology to navigate the IRS phone tree and wait on hold for you. When they reach a live agent, you get a call connecting you directly with that agent. So yes, someone (or rather something) is waiting on hold for you. The service was incredibly helpful for me because I had specific questions about what documentation I needed to keep for certain business expenses. Instead of organizing the wrong documents or keeping more than necessary, I got exact guidance from the IRS about what I needed to retain and how to organize it.

Does the scanner you mentioned work well with receipts? I have a regular printer/scanner but it doesn't handle small receipts well and they always come out crooked or unreadable.

The Brother scanner handles receipts extremely well! It has a dedicated receipt mode that adjusts the settings specifically for those narrow thermal paper receipts. Even faded receipts scan clearly, and it automatically straightens them. It also does batch scanning, so I can load a stack of different sized documents (receipts mixed with regular papers) and it processes them all correctly. The auto-feed feature is what makes it worth it for me - I just load everything in and walk away while it scans a stack of documents.

I do this and it works fairly well, but two important tips: 1) Make sure the entire receipt is visible and readable in the photo, and 2) Create separate albums for different categories (medical, business, donations, etc). Also, most smartphones timestamp photos which helps prove when the expense occurred. The IRS accepts digital copies of receipts as long as they're legible and show all the important information (date, vendor, amount, what was purchased). Just make sure you back up your photos somewhere in case your phone dies or gets lost!

Thanks for the tips! I'll definitely create separate albums by category - that makes a lot of sense. I was worried about the IRS not accepting digital photos, so it's good to know they're valid as long as everything is readable. I'll start backing them up to my cloud storage just to be safe.