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Whenever I send funds with XMR and use the refresh command to check my balance, Simplewallet will show a number of transactions, some adding money to my account and some withdrawing money from my account. Why is this?

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This is change coming back to your wallet. For instance, if you send 5 XMR, simplewallet might send that using a 10 XMR input, which it will then split and send 5 XMR to the person you are sending to, and send another 5 XMR output back to your wallet.

See section A, bullet 2 here for a bit more explanation in context:
https://getmonero.org/knowledge-base/protocol_explanation.html

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    just to add, this also means some of your funds may be locked for sending until the first transaction gets 10 confirmations
    – JollyMort
    Aug 26 '16 at 16:43
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    What about sending the entire balance. Since there's no extra funds to mix with, will it have less anonymity?
    – user4
    Aug 26 '16 at 19:54
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    Yes, but not for the reason you state. The coins spent mix with other outputs taken from the blockchain, which may happen to be also yours, but most likely aren't. If you send your entire balance, you typically use inputs that came from the same transaction, which means they're very likely to be the real inputs.
    – user36303
    Aug 27 '16 at 18:00

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