Hi @hbillings,
The leak sensor functionality detects when the two wires of a probe get shorted together. It should be possible to use a waterproof cable between your enclosures that you connect a probe to in the external enclosure.
Our SOS Leak Sensor has ports for 4 probes. If you’re using our Navigator flight controller there are ports for two probes and a connection to an SOS leak sensor, which would be 6 probes all together. If necessary multiple probes could be spliced together, and plug in via a single port, but that’s a fair amount more effort than the normal “plug in a probe” approach.