I've tried the following:
Setting mtu to 1400
Downgrading vagrant to 1.8.7 and VirtualBox to 5.1.38
Turn off firewall on host (osx) and guest (Ubuntu)
Turn off iptables in guest os
Ping works, but anything that requires ssl handshake will fail including curl and file_get_contents in php times out
Examples:
vagrant@scotchbox:~$ openssl s_client -connect www.google.com:443 -prexit
CONNECTED(00000003)
But using curl:
vagrant@scotchbox:~$ curl -iv https://www.google.com
* Rebuilt URL to: https://www.google.com/
* Trying 216.58.194.36...
* Connected to www.google.com (216.58.194.36) port 443 (#0)
* found 173 certificates in /etc/ssl/certs/ca-certificates.crt
* found 694 certificates in /etc/ssl/certs
* ALPN, offering http/1.1
It just hangs at this point.
PHP also has issues establishing handshakes:
Warning: file_get_contents(): SSL: Handshake timed out