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I'm trying to understand the different routing logics present in Ableton Live.

My goal is to route a Drum audio track to the side-chain external input of a compressor vst, whom effects a MIDI track where sits a VST Instrument.

The problem is the "Audio To" dropdown from the Drum track doesn't show my MIDI Track (and, specifically, its linked Compressor-VST channel).

I also tried to pass the Drum track through a Return channel and send it to the VST Instrument channel but it presents the same lack of choice in the "Audio To" selection list (it just shows the Audio channels and the default choices).

Anyone knows why? Probably I'm missing a point about the rules for sending tracks in Ableton.

Isn't possible to route to an Audio track to a MIDI track?

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If you were using either Compressor plug-in built into Ableton, you would be able to select your Drum track in the "Sidechain" panel of the compressor, accessed by pressing the little arrow in the top bar of the plugin. You don't need to use the "Audio to" function at all. I wouldn't be surprised if your VST Compressor has a similar function.

Basically you could combine your drum signal and instrument signal if you send them BOTH to returns, or both to the same return and then put the compressor on the return, but that would just combine the signals, not separate out which one is for side-chaining. Check the documentation for your vst plugin as to how to actually select a channel for the external input. Or just use the regular Ableton Compressor.

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