You want to know the maximum number of outbound emails / messages per connection when sending through the Email Security.cloud service.
The maximum number of messages per connection is 500. Therefore, it is recommended that your MTA is configured with a connection limit of 500 or less.
Please note this is different from the maximum number of recipients per message. For more info on that you may refer to: Error sending an email "452 too many recipients (#4.5.3)"
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This will clear the history and restart the chat.