I was asked to do the same but with Office365 and it didn't work. I am working on something else at the moment but it came to my mind that I might get this to work if I use stunnel. Below is an article on how to configure that (I know it is for SD but it might do the work) - Give it a try and let me know how it goes. I will try it after couple of hours:
Thank you for the suggestion, at this moment my Test Core is down (moving data centers) but I'll give it a try once its running (I do not want to install stunnel on my main core just yet )
Please let me know if you get it to work.
I created a test gmail account and use that to test.
That worked as well, so it must be the additional configuration/security that is being used when google is integrated with our company.
Stunnel may be the only know possible solution. Still to test.
Great motaz, I'll test it asap.
Motaz did you test this with LDMS or Service Desk?
I installed stunnel, and tried to follow the example but the email settings referenced for service desk are just not there for LDMS. And even when stunnel is running, outlook and regular gmail works but my company does not.
I tested it with LDMS. now when you configure your alert to send an email. The server address should be 127.0.0.1 and click on set credentials and then fill the account details. I have also tested it by scheduling a report to be sent via email.
I see 127.0.0.1, ok testing now.
Did you start stunnel? When you run the Stunnel GUI, do you get any errors?
I think the stunnel is running, I ran it by going to C:\Program Files (x86)\stunnel\bin\stunnel.exe this creates an icon by the clock. Now when I hover my mouse over, it says server idle but I dont see an option to start or anything like that.
I look for a stunnel service but there is not one.
I have the feeling that I'm missing something.
This is how the log looks like:
If you open the start menu you will find something related to stunnel service installation. However, from the screenshot I can see that it is working. If you try to schedule a report and configure the SMTP with the desired account, do you face any issues?
I reinstalled the stunnel, since I did not selected the tools option during install, the service option was not available.
After the install, I Installed the service, Stunnel TLS wrapper is now running.
In the client section of the stunnel.config I only have this section uncommented:
client = yes
protocol = smtp
accept = 127.0.0.1:25
connect = smtp.gmail.com:465
verifyChain = yes
CAfile = ca-certs.pem
checkHost = smtp.gmail.com
OCSPaia = yes
I tried the test again after all that, but got the same result, we are using okta verify, I want to believe that that application is blocking the authentication.
I'm setting up a new account (just for alerts, and I'll try again)
I really, really wish IVANTI/LANDESk LDMS would have a more robust integration with enterprise email.
Thanks for your help Motaz