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I am trying to setup an RPC connection between monerod and monero-wallet-cli over SSL. For monerod, the recommended way seems to be to use nginx as a reverse proxy and add SSL support there. How do I use this SSL connection from monero-wallet-cli (and/or the GUI wallet too)?

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Once you have setup the tunnel, it is equivalent to having monerod running in localhost. It is transparent for monero-wallet-cli and monero-wallet-gui.

The only difference, that i noticed so far, is that it doesn't accurately detect network failures, as the connexion with the tunnel manager stays up.

You can see here an example of setup using stunnel.

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    So the answer is that the client DOES NOT support SSL connections but an external program can be used (such as stunnel) that can provide these services. – tazmanos Feb 26 '17 at 21:57

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