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A user on Ethereum SE posted the following

As you noticed, there is no way to send a single from multiple addresses. There is always just one sender.

For Ether transfers the Ether value is always taken from the sender's balance and you can't take it from other accounts (that would be a rather big security hole) - even if you have their private keys.

What I don't understand is why is this deemed a "big security hole" if the sender owns both private keys? What is the risk?

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I wonder if I'm allowed to answer this :)

I edited the quoted answer as it could've been interpret incorrectly. Now it says:

For Ether transfers the Ether value is always taken from the sender's balance and you can't take it from other accounts (that would be a rather big security hole). You can't take them in one transaction even if you have their private keys.

So one transaction is always from one account (address), and therefore with one private key. The note about security hole refers to the fact that you shouldn't be able to take funds from other accounts arbitrarily.

There is no functionality to send a transaction from multiple accounts or to somehow collect funds from multiple accounts in a transaction, even with private keys. A transaction doesn't understand anything about keys - the private key is used as a sort of an envelope for the transaction, to sign it. And you can't sign a transaction with multiple keys.

So this kind of multi-send functionality has to be done off-chain with multiple transactions.

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