Hi, we have an email template module being used to send a number of documents to customers, generated from an app in custom cloud. The client was using office 365, and after tweaking a bit the java we've managed to send emails with attachments (TLS) via office 365 smtp. Now, the client changed from office 365 to Google Apps and new email system (google email from google apps), and as we've used gmail smtp before in other mendix apps, all good ...we thought. However, we have an issue with emails being sent as google apps security is not letting the Mendix app to sign into the account. If I use my own gmail account, I am able to change the "less secured app" settings to "enabled" and emails are sent correctly from the mendix app (inc attachments). The problem is that client has a Google apps account which doesn't have or allow the "less secured app" setting. I have tried all combinations for the port number, and using SSL instead of TLS, but that didn't work either. How can we bypass the fact we cannot set enable access for less secured apps? Actually why does google think Mendix app is a less secured app? We are running in version 336 of the modeler in the old cloud (custom cloud), could this be an issue? Or do we need to add some special Certificate to the settings? The settings used at the moment are as follows: java TLS = true java SSL = false smtp: smtp.gmail.com port: 587 username and psw: <customer email address from google apps mail> from email: same email as username As mentioned above, using a personal gmail credentials with less secured access enabled works perfectly, using the client's google apps email credentials doesn't work due to setting not available for google apps accounts. LR.