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Title pretty much explains my problem. I like having the option to encrypt when I mail certain contacts, but that doesn't mean I want to do it every time — having to disable encryption 90% of the times I email my boss is kind of annoying.

Can someone tell me what I'm missing? I can't find the option to disable this anywhere.

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Just adjust the settings: Mail.app > Preferences > GPGMail > Composing > Encrypt when all keys are available.

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