David,

The configuration sample shipped with stunnel includes a section designed to send smtp mail via GMAIL. Something like this:

[gmail-smtp]

client = yes

accept = 127.0.0.1:25

connect = smtp.gmail.com:465

verifyChain = yes

CAfile = ca-certs.pem

checkHost = smtp.gmail.com

OCSPaia = yes

protocol = smtp

[email protected]

protocolUsername=youpassword

However, recent security changes on GSuite may impact this. Google is enforcing the Oen Authentication protocol (OAuth) . Check this:

https://www.bleepingcomputer.com/news/security/google-to-force-oauth-in-g-suite-to-increase-security/

I think you can still make it work if you follow the instructions published here:

https://support.google.com/a/answer/176600?hl=en#zippy=%2Cuse-the-gmail-smtp-server%2Cuse-the-restricted-gmail-smtp-server

On Office365, the situation is similar. Microsoft has been disabling legacy protocols, but you may be able to achieve what you want following this guide:

https://docs.microsoft.com/en-us/exchange/mail-flow-best-practices/how-to-set-up-a-multifunction-device-or-application-to-send-email-using-microsoft-365-or-office-365

Now, If this helps you, feel free to send me some money at my Paypal :)

regards,

Jose

On Saturday, April 24, 2021, 03:50:54 AM GMT-5, David Rose (dsr) <[email protected]> wrote:

I need an Stunnel config that will allow my Windows app that only can

send SMTP without any authentication or encryption to be able to send

email via Gmail or Office 365.

Is this something that someone would be able to write for me and if so,

what would you charge ?

Thanks

David

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