Maybe... we'll try it but there are mixed comments if you follow the link attached. It would be nice not to have to spend a whole morning trying to sort out how to get this to work.

We did have issues with STunnel but in that thread was this which works!

"Google actually accepts non-SSL SMTP connections on one of their servers, aspmx.l.google.com on port 25. Set the Xerox to send via that and set your username and password to a Google Apps account. "

So, set the mail server to: aspmx.l.google.com and the port to 25 with the Server Requires Authentication unchecked and it should work.

I hope this is helpful for other users trying to find a solution.

Thanks for posting this! Others will appreciate it I'm sure.

I am not clear on what I should do for my client.
They email out Invoices through Outlook and the customers that use Gmail, are not getting the pdf file.

Have the clients that use Gmail check their account settings to see if they have disallowed attachments.

If Google ever decides to take down/rename their non-SSL required SMTP server, or you have a client with an outgoing email server that requires SSL encryption, it isn't too difficult to set up direct emailing in Adagio via Stunnel. There are 3 things to note:

1. Ensure the service is properly defined in stunnel's configuration file. There are examples and premade services for gmail in the default config file. It should be something like:
[whateverservicenameyouwant]
client = yes
accept = (the local IP address of the PC the stunnel service is running on):(the port Adagio is set to send mail through)
connect = (the address or name of the smtp server):(the port it is expecting to send mail through)

2. Change the outgoing server in Adagio's email setup to be the local IP of the machine running the stunnel service and ensure the other options are correct.

3. You may have to experiment a little with some of the extra security options as they are provided in the sample stunnel configuration file, depending on what the mail server you are sending through is 'expecting'.

Happy Wrapping!