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I've been an independent contractor for about 2 months now. I'm saving receipts for all my business-related expenses, and I use Mint.com to track all my personal finances -- Everything business related is "tagged" as "LLC" (I'm not really an LLC, but I aspire to be =D). I also recently found Expensify.com, which has an awesome Android app for taking photos of receipts, and I've been using this as well.

So all in all, I have my original receipt, my mint.com transaction history ("Find all transactions tagged as LLC"), an Expensify transaction history (which is the same thing) and pictures of all my receipts in Expensify. I'd like to simplify all this; If I were to get audited, what would I need? Which of these should I keep using, and which are just extra work for no gain?

Some people have told me to keep the original physical receipts. Some people say a summary sheet of income/spend is enough. Do I need my original receipts? Are photos of these receipts enough? Do I need to have the itemized list of expenses (e.g. at McDonalds, $1 double cheese, $1 fries, which means I need to keep receipts/photos) or just a per-store transaction history ($2 at McDonalds, $2 at Burger King, in which case receipts are overkill and Mint.com's logs would be sufficient)? Do I have to prove what I bought, or just where I spent the money?

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While IANAL (tax or otherwise), I have always found that keeping original receipts is the only way to go.

While anything can, at some level, be forged or faked, a photo is one more step removed from the original. A mere listing on a web site isn't much proof of anything.

Keep your originals for a suggested seven years; while the IRS is trying to audit much faster than that, and any inkling of fraud can be investigated at any time, you should be well and clear with originals kept that long.

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    Ugh, thanks for the answer, but this is the worst news I've had all day :-p and here I thought I might be able to go completely paperless... – linkedlinked Apr 8 '10 at 2:58
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    Another consideration against using online services to go paperless is that they may not be around in 7 years, or may not keep 7 years of history. I'd hope you have an option to download your info, but...it's less than certain. I love the cloud--this is just something to keep in mind. Maybe if these places let you export your data annually or monthly... – Michael Haren Apr 8 '10 at 21:12

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