I am also experiencing this issue with the Wifi Pineapple Tetra.
Recon works fine from the Pineapple itself, however, the Pineapple will disconnect from the cloud itself once the recon module has been enabled and won't reconnect until I restart the instrument. I have re flashed the latest firmware (2.7.0) onto the Pineapple and has not rectified the issue. Version on Cloud C2 is 2.2.0. I am running the cloud c2 server on a raspi 4 running dietpi. All other Hak5 gear works completely fine with cloud c2 it is just the pineapple I am having issues with.