Hitting AWS Simple Email Service through a NAT Gateway

[Joshua Silsby]

I have a jira server and a confluence server sitting in private AWS subnets with NAT Gateways.  Jira has no issue hitting email-smtp.us-east-1.amazonaws.com:465 but confluence always times out.  

[Stephen Sifers]

Hello Joshua and welcome to the Community!

To understand more about your issues with emails within AWS when using a NAT gateway I will need a bit more clarification. To understand your NAT rules and how the services are configured, could you please let us know if Jira and Confluence are on the same server (I know you mentioned you have two servers, but I want to clarify to avoid confusion)? The reason I ask is Jira may be interfering with the connection when Confluence is attempting to talk out. If this is the case, Stop Jira and attempt a test with Confluence to see if it connects.

If they’re on separate servers, ensure you NAT rules consider the ports used for both and they each either have a separate IP/Port translations available to communicate. If they’re sharing an IP/Port this may be causing your connection issue.

Additionally, ensure your configuration is correct within Confluence to ensure it’s able to connect. Please refer to the guides at: 

1. Sending Email Through Amazon SES From Software Packages
2. Configuring an SMTP mail server to send notifications

We look forward to hearing back to ensure you’re able to send emails within Confluence and Jira.

Regards,
Stephen Sifers

[Joshua Silsby]

Thanks Stephen.  I got the JNDI method to work, but natively within confluence it continues to fail, which tells me, in conjunction with the Jira server in the same environment working, A) the configuration/environment of the server and AWS VPC are fine and B) the issue is internal to Confluence in some way.  I will continue to use the JNDI method, seems hacky though...