I enabled SIP capturing and left all the config at defaults
but I'm not seeing anything captured in the Homer interface.
 Is there something else I need to do to turn it on?

To your question, though, when I do a tcpdump filtered on
port 5061 and call either 8-200 (dir to ext 200 vm) or 101
(vm access #) I get traffic like you see in
Sipx-O365_TlsHandshake_failed.pcap.  Packet 13 is client
certificate request and 15 is the empty response.  I don't
get anything when I call 200 and let it roll.  For
comparison, I get ssl_handshake_test.pcap when I run this
from Sipx shell: "openssl s_client -connect [unique
ID].um.outlook.com:5061 -cert /etc/sipxpbx/ssl/ssl.crt -key
/etc/sipxpbx/ssl/ssl.key -CApath
/etc/sipxpbx/ssl/authorities/". You can test yourself by
using wildcard-latam.um.outlook.com:5061 as the destination
host.

(I apparently can't upload those two caps but it's easy
enough to replicate using wildcard-latam.um.outlook.com as
the gateway address)

Attachment: Sipx-O365_TlsHandshake_failed.pcap
Description: Binary data

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