

Step 3 – Verify the stunnel is listening for connections That would look like:Īfter the file has been modified, replace the existing nf in the Program Files\stunnel directory with the new one.įinally start the stunnel service. You can remove the 127.0.0.1 portion of the address to have the service listen on all IP Addresses. This is only useful if the application that needs to connect to Microsoft Online resides on the system that stunnel is running on.
#Stunnel office 365 config how to#
Continue reading for details on how to configure and use stunnel.
#Stunnel office 365 config install#
You can install stunnel on a server or workstation in your environment and configure your devices which don’t support TLS or POP3 over SSL to connect through that server to the Microsoft Online Services. This allows you to configure your applications to connect without using SSL to the stunnel service, and then stunnel builds an encrypted tunnel to the Microsoft Online POP3 or SMTP services. Stunnel listens for non-SSL connections and converts them to SSL or TLS connections.

The secret is a free application called stunnel.

After doing a bit of research we think we’ve found a good way to get these applications to connect without SSL and on the standard POP3 or SMTP ports! Examples include not being able to connect on a non-standard port, or not having the ability to connect over TLS or SSL. In some cases these applications or devices don’t support the requirements for connecting to Microsoft Online. A common problem that we run across while doing migrations is legacy applications or devices which use SMTP to send mail or POP3 to retrieve mail.
