Chilkat MailMan has HTTP proxy properties for its mail connections. On an existing MailMan instance already configured for the SMTP service, apply the proxy settings before connecting:

mailman.HttpProxyHostname = "proxy.example.net";
mailman.HttpProxyPort = 8080;
mailman.HttpProxyAuthMethod = "Basic";
mailman.HttpProxyUsername = proxyUser;
mailman.HttpProxyPassword = proxyPassword;

This C# fragment selects Basic proxy authentication. The documented alternative is NTLM; its optional Windows domain is supplied through HttpProxyDomain. Leave the authentication-method property empty when the proxy requires no authentication. In that branch, the HTTP proxy list offers addresses for a permitted public SMTP route. Retain no proxy username, password or domain for the candidate, and confirm that it permits the mail server’s actual host and port.

Retain the application's SMTP host, port and TLS settings on the same MailMan object. The HTTP endpoint above is the intermediary that carries that connection.

The proxy must permit a CONNECT tunnel to the actual mail-server port. A service restricted to forwarding ordinary web requests cannot carry SMTP just because it accepts an HTTP connection from MailMan.

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