+1 It looks like the reason the previous change broke is because Apple again changed the certificates that they used…
I tried running some debugging steps (namely, using SSLPoke as suggested in Icloud binding - General SSLEngine problem - #27 by The-Elk), and the SSL certificate authenticates successfully in SSLPoke, but for some reason it fails in openHAB. Still trying to find diffs in the logs when -Djavax.net.debug=ssl is enabled…