@eskimo thank you -- filed it, public copy at http://www.openradar.me/radar?id=5552164072062976 btw that's a neat idea for sharing an address, (let myEmail ...)

see https://github.com/libreswan/libreswan/issues/1450

With some help from libreswan, it seems a temporary workaround is constrain the vpn server to only one proposal for ike and esp. The issue happens when macOS rekeys, sending an incorrect order of proposals. For example, if using libreswan, edit properties in /etc/ipsec.d/ikev2.conf rekey=no pfs=no ike=AES_GCM_C_256-HMAC_SHA2_256-ECP_256 phase2alg=AES_GCM_C_256 Then in the VPN Profile, set <key>EnablePFS</key> <integer>0</integer> <key>ChildSecurityAssociationParameters</key> <dict> <key>DiffieHellmanGroup</key> <integer>19</integer> <key>EncryptionAlgorithm</key> <string>AES-256</string> <key>IntegrityAlgorithm</key> <string>SHA2-256</string> <key>LifeTimeInMinutes</key> <integer>1440</integer> </dict> <key>IKESecurityAssociationParameters</key> <dict> <key>DiffieHellmanGroup</key> <integer>19</integer> <key>EncryptionAlgorithm</key> <string>AES-256</string> <key>IntegrityAlgorithm</key> <string>SHA2-256</string> <key>LifeTimeInMinutes</key> <integer>1440</integer> </dict>