Instructions taken from Amazon's docs and modified as necessary.
- Download from stunnel's download page
- Run installer w/ default options, create self signed cert by answering questions
- Open the
c:\program files (x86)\stunnel\stunnel.conf
file in notepad - Clear all the server configs (under
Example SSL server mode services
section, won't have aclient = yes
line) - Create a new client config:
[smtp-tls-wrapper]
accept = 127.0.0.1:2525
client = yes
connect = email-smtp.us-east-1.amazonaws.com:465
- Start
stunnel.exe
and ensure no errors are reported (you will get a little systray icon) - If it succeeds you can optionally install as a service, by running
stunnel.exe -install
at command line (note this installs the service but doesn't start it, so start it) - Test the connection, at cmd line run
telnet localhost 2525
and you should see an SMTP response from Amazon's server (if telnet isn't installed, add the feature in Server Manager / Features / Add Feature)
- Set Smart Host as
[127.0.0.1]
(include the brackets) - In the Outbound Connections section, set outgoing port to
2525
(like the stunnel.conf file) - In the Outbound Security section, set authentication information to your Amazon SMTP credentials, set it to basic authentication (NOTE: DO NOT CHECK THE TLS CHECKBOX)