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How to use Outlook express with TLS - Printable Version

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How to use Outlook express with TLS - Rafael - 06-27-2019

Use Stunnel, a tool acts as a proxy. You can configure it to establish an SSL connection to a given host and port when a connection to a given local port is made. Thus you could configure OE to connect to local port on the machine running Stunnel, which might then connect via SSL to smtp.example.com:465 using a more modern TLS version supported by Stunnel (but not directly by OE).

Stunnel download page:
https://www.stunnel.org/downloads.html

Download:
[Image: zip.gif] stunnel-5.53-win64-installer.zip

For 32bit:
[Image: zip.gif] stunnel-5.23-installer.zip


Now, this example is for COX, with cox server. You must replace the servers ('smtp.cox.net' and 'pop.cox.net') with yours.

Steps:
1. Download and install stunnel

2. right click on stunnel icon on tray and click "Edit configuration"
[Image: attachment.php?aid=603]   

3. Insert this on stunnel configuration text file that will open with notepad and save the file (File>Save)

NOTE: these servers and ports are an example for cox.net. Replace the servers ('smtp.cox.net' and 'pop.cox.net') with your's.
Code:
Code:
[cox-pop3]
client = yes
accept = 127.0.0.1:995
connect = pop.cox.net:995
verifyChain = yes
CAfile = ca-certs.pem
checkHost = pop.cox.net
OCSPaia = yes


[cox-smtp]
client = yes
accept = 127.0.0.1:587
connect = smtp.cox.net:587
verifyChain = yes
CAfile = ca-certs.pem
checkHost = smtp.cox.net
OCSPaia = yes
[Image: attachment.php?thumbnail=596]   



4. Right click again on stunnel tray icon and click "Reload configuration"
[Image: attachment.php?aid=604]   

5. Open outlook express and edit your COX account. On the "Servers" Tab, replace your servers (both incoming and outgoing) with 127.0.0.1
[Image: attachment.php?thumbnail=593]   

6. Go to "Advanced" Tab and enter ports (587 for SMTP and 995 for POP3), UNCHECK SSL
[Image: attachment.php?thumbnail=594]   

That's it. Try now to send and receive emails.