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I want to be able to select per dictation whether I want to send it to the cloud server or to a local server. Can I do that?

Yes, with SpeechLive you can select on a per dictation basis whether you send the dictation to the local server or to the SpeechDrive online storage. In the SpeechExec general settings you can specify the behavior of the application. Go to General Settings>Dictation>Dictation finished and specify the “Dictation finished” behavior.