C3700 email logs failing

I've been troubleshooting the ability to e-mail the netgear logs from my C3700. I've tried both sending e-mail to an internal e-mail server (confirmed that the internal server is working via a manual smtp mail transmission via 'telnet <IP> 25' and also to Google's GMAIL SMTP service. Both end up with log entries like the below (message of "[email failed] Failed to Connect Tcp Socket! 360" ):

I have also run tcpdump (wireshark) on the e-mail server and see a bunch of TCP Retransmission issues. Has anyone else seen/experienced this issue and found a way to resolve it?