EBS 12.2 Workflow Outbound SMTP to Office365

We are on EBS 12.2.6 and are moving to Office365. I'm trying to set up configuration for our Workflow Mailer to connect to IMAP (inbound) and SMTP (outbound) using Office365. I believe we have all the patches loaded per Doc ID 2077434.1 and others I have been reviewing.

I can use the Linux command line scripts to successfully connect both to IMAP and SMTP, but when I set up the Workflow Mailer configuration within EBS, it fails on the SMTP connection.

I've used the $FND_TOP/sql/afsvcpup.sql script via sqlplus to set the configuration on the back-end to match what I'm using on the command line but when I go back into EBS, I still cannot get SMTP to validate.  We had a previously configured keystore that I did update with the Office365 certs as well as updating $AF_JRE_TOP and $OA_JRE_TOP cacerts keystores. I also set the "SSL Trust Keystore" to NONE so it would default to the jre cacerts file instead of our custom .keystore file.  Do you have to bounce apps after changing those settings?