Allworx Technical Support Forum

Have an older 6.x that stopped sending emails to a smart host. For several years the Allworx would send VM emails to users. It was sending to an onsite IMail mail server. We got rid of the Imail server and went to O365 and could never get the thing to send to O365 so I set up an SMTP relay using IIS. The relay will send emails to O365 without issue but the Allworx just will not send an email to the relay. The only thing that has changed is the IP of the server that the Allworx should send the emails to. It's baffling me as to why it won't send emails just as it did in the past when the only thing that changed is the IP. The Allworx event log is useless because it apparently doesn't log email events and I know it's not even trying to connect to the relay.

I should add to this that a few weeks ago the Allworx did send an email to the relay once and then wouldn't send any after this. Again, I changed nothing to make it stop sending. There are no firewalls or other restrictions between the Allworx and the relay.

What version? Always be on the most recent version you can (and read the release notes).
You may not need to have such a complicated way to accomplish your goal. The Allworx can act as its own SMTP server. Try reseting the E-mail section to the defaults and starting from there. As far as the System Events, v8.4 and v8.5 provide more details. Be sure you have checked DEBUG as a filter. This will give you the most detail.
Have you checked the logs of your relay? You say that the Allworx isn't sending the E-mails. How do you know? Check the Allworx E-mail queue to see if there are unsent messages. Lastly, you should do a packet capture from the Allworx to determine if in fact no SMTP traffic is being sent.

Whevever I run into these issues, I just setup a gmail account to send emails.

Keep it simple.

Even using Gmail to relay voicemail started to have issues (when they locked down "insecure" SMTP accounts - [but the fix is to use application specific passwords]), so I ran my own email server out of my house, and setup DNS SPF and DKIM records on it. A bit of overkill, but I did it for the knowledge and experience.