Monitoring while recording samples from Ableton

Hey y’all. Here’s my setup:
Overbridge on MIDI track
8 audio tracks receiving separate audio

My question: how can I say play a sound on a virtual instrument in ableton, send to digi for sampling and also monitor it. It doesn’t seem posssible. Only if I switch output to Digi

Probably not enough info, but I can’t seem to find a way