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Do you have to sync the entire blockchain before transferring from a monero wallet via the command line??

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You need to have the wallet sync, but you dont are forced to have the bockchan, you can sync the wallet and transfer from it using an remote node. When syncing the wallet will run all the blockchain (or from specific high) to check your belonging inputs When transfering the wallet will ask the node for inputs to mix with yours, this can leak some information from your transactinon and compromise your privacy level

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from the previous question: yes, unless you connect to a remote host (node), which you may or may not want to do depending on your personal level of trust in the remote host. lightweight nodes/wallets don't exist yet.

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