Port Forwarding with Microsoft Outlook

Port forwarding offers a quick and easy way of keeping your personal and company email private and secure. The following instructions will help you quickly configure your TinyTERM product and Outlook to work together to keep your email secure.

When using port forwarding, there are two external hosts that you will be communicating with: the secure host that is running SSH, and the unsecure host that handles email. These instructions will configure your desktop or laptop system to send and receive email over the secure host, who will communicate with the unsecure mail server. In some cases, the mail server will be running on the same secure server as SSH. In this case, you'll use the same host names for both.

In the examples below, mailhost.com is used to represent your mail server, and securehost.com is used to represent the secure server running SSH.

To configure your TinyTERM product for port forwarding, you need to first establish a secure connection/session with your secure server. To do this, launch TinyTERM and then select Edit|Session Properties... to display the Session Properties menu.

Click on the "Session" tab.
Enter the name of your secure host in the "Host name, IP address or phone number" box.
Make sure the "SSH" connection type is checked.
Select "Apply" and then "OK"
Open a TinyTERM session to the secure host. You may be prompted to supply a username, password, and the secure host's encryption key may be displayed.

Next, you need to secure your outbound SMTP connection. Select Edit|Session Properties... to display the Session Properties menu. Click on the "Port Forwarding" tab.

Enter "MySMTP" in the "Connection name" box.
Make sure "Local to remote forwarding" is selected.
Enter "10025" in the "Local port" box.
Make sure "Remote host is different from SSH server machine" is checked.
Enter the name of your mail server in the "Remote host" box.
Enter "25" in the "Remote port" box.
Select "Add" to add the MySMTP configuration to the "Port Forwarding Connections Data List" box.
Select "Apply".

Next, you need to secure your inbound POP3 connection.

Select "Clear" to empty the entry form.
Enter "MyPOP3" in the "Connection name" box.
Make sure "Local to remote forwarding" is checked.
Enter "10110" in the "Local port" box.
Make sure "Remote host is different from SSH server machine" is selected.
Enter the name of your mail server in the "Remote host" box.
Enter "110" in the "Remote port" box.
Click "Add" to add the MyPOP3 configuration to the "Port Forwarding Connection Data List" box.
Click "Apply". Click "OK".

Now that TinyTERM is setup for port forwarding, you need to configure Outlook to operate through your new secure connection. Launch Outlook, and select Tools|Accounts... to view a list of your active email accounts.

Select the account you wish to make secure, and click on "Properties". Select the "Servers" tab to display the server information.
Enter "127.0.0.1" into the "Incoming mail (POP3)" box.
Enter "127.0.0.1' into the "Outgoing mail (SMTP)" box.
Click "Apply".

Now you'll configure your email account to use the secure ports.

Select the "Advanced" tab.
Enter "10025" in the "Outgoing mail (SMTP)" box.
Enter "10110" in the "Incoming mail (POP3)" box.
Click "Apply".

If your secure server is different from your mail server, you may need to configure the outgoing mail server for authentication.

Select the "Servers" tab.
Make sure the "My server requires authentication" box is checked.
Finish Outlook setup by clicking on "Apply" followed by "OK" followed by "Close" on the opened dialog boxes.

You are now setup to send and receive email over a secure, encrypted channel!

It is important to remember that TinyTERM must be running and a session established with your secure server in order for port forwarding to work properly. If TinyTERM is not running, or you don't have a session established, Outlook will be unable to retrieve your email and will respond with "Mail Delivery Error" messages.

The server names used above should be changed to the names or IP addresses of your actual secure server and mail server. The 10025 and 10110 port numbers used in the examples may be changed to anything above 1024. Port 25 is assigned to be the SMTP server and must not be changed. Likewise, port 110 is assigned to the POP3 server and must not be changed.