Does bluetooth file transfer work between Mountain Lion and El Capitan?

I am unable to transfer files via bluetooth between a laptop w MacOS 10.8.5 and a laptop w MacOS 10.11.2. Is this expected?

Observed:

- Pair the two laptops

- Initiate first file transfer (Finder > Bluetooth Menu > Send File...)

- File transfer successful

- Initiate second file transfer

- File transfer failed ('unable to connect')

Expected:

- File transfer should work more than once

More info:

- After file transfer failed, I unpaired and repaired several times, with no luck