I have the RV320 router with firmware v1.3.1.12 (2016-04-27, 10:46:12) and have not been able to get it to successfully e-mail logs (using the send now command to test) despite trying every possible set of SMTP server settings in the setup menu for multiple e-mail service providers. I have tried the correct settings (tested from e-mail clients and even other LAN devices capable of sending logs, like a NAS) for Verizon, Gmail, and Outlook with no results on the RV320 with one exception. The RV320 did connect with Gmail to send a log but only when using port 465 SSL AND setting Gmail preferences to allow "insecure devices" to login, which is not an acceptable workaround. The router would not connect to Verizon using port 465 and SSL and would not work with Gmail nor Outlook with the preferred/common method of port 587 using TLS.
The issue seems to be a failure or lack of capability of the RV320 to properly negotiate an SMTP session using the now common and required STARTTLS SMTP security handshake. Interestingly, I tried a free online SMTP TLS test relay site to receive the SMTP commands from my router as the "man in the middle" and pass them on to Outlook while logging the session for diagnostics. Then it worked and the e-mail was sent, but apparently because the relay server negotiated the STARTTLS handshake with Outlook's SMTP server after receiving the SMTP commands from my router. This rules out issues with my WAN connection and points to what the RV320 is trying to do when interacting with the SMTP servers.
I have a case open with small business support that has been elevated and now they want me to capture LAN and WAN packets and send them (not sure why LAN because the RV320 communicates with SMTP servers on the WAN side). This is going to be time consuming and pointless in my opinion because I was hoping this can be simply be replicated in the lab with another RV320 with the latest firmware trying to connect to any common ISP/e-mail provider via SMTP. If it doesn't work on a test RV320 with this firmware that can be known in 5 minutes. In the mean time it would be great to hear from anyone experiencing the same issue using this firmware and what the resolution was.
UPDATE:
WAN packet captures show that the RV320 wont even try to initiate an SMTP session with the SMTP server unless it responds to a ping request from the router. Outlook and Verizon SMTP servers do not respond to ping so the RV320 aborts. Gmail's SMTP servers do respond to ping, so the RV320 starts a SMTP with TLS session on port 587 but then gmail rejects the connection as coming from an "out of date" or less secure device.
