eigenvector7

@daoudnagy – unfortunately not in a structured way. Short story – I was able to get the postman working but couldn’t really figure out why it was/is not working.

Long story – in frustration, I created a sandbox site and reset the plugin on that site. Updated the wordpress and deleted the plugin and reinstalled it. Launched the auto-configuration and nothing happened(stuck at step 3). Removed it again out of desperation to get a clean slate and then tested the following server (instead of smtp.gmail.com or others). https://www.googleapis.com and realized for the first time since the issue happened that I was able to atleast hit the google API specific port but not the SMTP port. It surely points to either my host blocking SMTP ports or maybe this server isn’t meant for SMTP. I then followed the instructions (instructions)to configure the OAUTH2.0 and switched to OAUTH2.0 mechanism and things started looking rosy from there one.

Unfortunately, on my live site I wasn’t able to replicate the above (since I didn’t want to nuke the plugin completely) and the connectivity tests still stays hung there but I was able to manually configure the setup to exactly what I had with the above mentioned sandbox and things started working. Hope this helps – good luck!!