The SMTP email settings you defined in your Dynamic AI instance are used by both manual and scheduled sending, so if one works, the other should work. Make sure:

  1. The 'AGENT' user exists in your system.
  2. The password you have assigned to that user matches the one you entered into AGENT.ini
  3. AiAGentPing.exe and AGENT.ini both reside in the same folder

You can manually execute AiAgentPing to make a test and prove if it can successfully send an email. (It's successful receipt is unrelated.) If it is successful you will see it updated the "last" and "next" execution date-time stamps on scheduled records due for sending at the time AiAgentPing was executed. If it fails, an error should be written to the log, that you can view under 'General Alerts' on the Admin menu under Activities, Log Alerts.

Gmail requires authentication and use of SSL -- and the last time I used GMAIL for this I used port 465. Also GMAIL has introduced more stringent security so if you don't allow devices and applications that GMAIL now considers insecure (Outlook on my Win10 machine was an example of this.) you either have to turn this setting off in GMAIL or make an exception in GMAIL. (I don't recall how I did this for Outlook.)

In case you tested manual emails using a local SMTP server, and then changed your SMTP server to use GMAIL in order to do scheduled emails, you needed to define various SMTP parameters in Dynamic AI system parameters. See Dynamic AI System Parameters.pdf that you can find with the other doc files on the "Documentation" link in the sticky post at the very top of this forum with title "Dynamic AI Resources".

Lastly, depending on security rules on a given email server, the email domain of the sender might be required to be the same as email server domain, i.e. might not allow sending an email from In Dynamic AI, the user profile specifies that user's email, which defines the "from" address.