TMS 14.5 Failed to Verify E-mail Address

[Michael Bruce]

Introduction:

TMS 14.5

TMSPE 1.0

Windows Server 2012 R2

I'm using STunnel on the server which I've tested is working for TMSPE as it will email me my credentials.

Issue:

I enter all of my information into the AdministrativeTools>Configuration>E-mail Settings. The information is correct but I get the error:

"* E-mail Settings not saved: Failed to verify e-mail address"

Troubleshooting:

Ran a packet capture filtering for SMTP and this seems to stand out:

Response parameter: 5.7.0 Must issue a STARTTLS command first. f32sm1715843iod.30 - gsmtp

Gmail appears to end the connection at that point if I'm reading it right.

Question:

My guess would be that STunnel is not converting SMTP to SMTPS but I've verified that the TMSPE emails are going out correctly so I'm pretty sure that indicates STunnel is fine.

I'm all out of steam at the moment, anyone have any ideas?

[Michael Bruce · Accepted solution]

So I've solved this issue and figured I would follow up in case others run into something similar:

As far as I know, TMS doesn't support SMTPS and therefore you need a program to change traffic on 25 to 465 or 587. STunnel is a light weight program that can achieve this for us.

After installing STunnel and configuring it to connect on 25 and accept on 465 (Don't forget to also install the service and start it by navigating in cmd to the STunnel directory and typing "stunnel -install" "stunnel -start") we can then add all of the Gmail SMTP information into AdministrativeTools>Configuration>E-mail Settings Making sure that you add 127.0.0.1 as the SMTP server.

You will also need to add that information to: the AdministrativeTools>Configuration>ProvisioningExtensionSettings 

Once completed entering those details restart the STunnel service and also restart the TMSProvisioningService (It will take a couple minutes to restart, monitor the java process in task manager to see when memory stops climbing). 

If all went well, you should be able to send emails through a secured email service without any issues thus resolving the SMTP restriction in TMS.