I ran into a issue just recently where I migrated a customer from a 2008 R2 server to a 2016 server and instead of doing a back up restore I configured the system from scratch. So it essentially is a new system running but with the same hardware and all the hardware had download the new configurations. The issue we ran into is that a remote site with a singe SG90V switch with external analog trunks would not play the auto attendant recording when some one would call in. It would just play the default ShoreTel back up auto attendant recording, no matter how we tried to route the call to the correct auto attendant.
We tried routing the call to a user and forwarding to the AA, we tried sending it to a route point and then the AA, we tried all sorts of things to try and make this work. The auto attendant was reachable if you called it internally, it was reachable if you called it externally at the HQ site, but the site it was supposed to work at could not get the AA to play. There were no communications issues, TMS was connected, LSP worked between the equipment everything seemed to be configured correctly.
It turns out that the customer uses Office 365 for voice mail to email, and the ShoreTel SMTP relay was configured to use port 587, it was using TLS, and had a smart-host configured as well as a user account to authenticate to Office 365 with. ShoreTel uses SMTP port 25 to transfer AA greetings to V switches, and because the customer was using SMTP on 587 for Office 365 the recording could not be transferred to the V switch.
So to test we set the SMTP port to 25, removed TLS, and the user account, re-imported the greeting to the AA and tested. We were able to get the AA to play once this took place, but it broke their voice mail to email. This aspect is very important to them so we reverted the changes, but because the V switch already had the AA greeting saved the AA continued to work. The issue is going to be when they want to change the greeting we will have to either find a different work around or we will have to record the greeting, break voice mail to email re-import the greeting and then reconfigure voice mail to email.
As soon as i have more information about a possible work around or resolution to this i will update this post.
