Using Outlook/Outlook Express to Send Mail Through a Firewall

I had been experiencing a certain computer problem for months, and finally arrived at a solution the other day, so here it is for all who might be dealing with the same issue:

I regularly use my laptop at our local library. Actually, I occasionally teach seminars at the local library, and between classes I like to catch up on email correspondence. Receiving email was, as usual, no problem. Sending email, however, was a major pain. In yet another ongoing crusade to control spam, the library’s firewall prevented email of any kind to be sent via port 25.

For a while, I used webmail to send mail, but this was extremely inconvenient since I have, due to the nature of my business, about ten different email accounts that I send/receive email through. Checking each one of them individually through webmail was time consuming and laborious. Furthermore, most days I would open up Outlook Express (my mail client of choice) without thinking and download my mail. To reply, I then had to log into webmail and copy and paste the original message into the reply.

So I tried other options, including creating an SSH tunnel via Putty (I couldn’t get it to work, even with expert advice). Seems my mail server isn’t configured properly to allow this kind of traffic.

Anyway, after months of workarounds and dealing with the nuisance, I suddenly remembered seeing “IMAP” when adding an email account in Outlook Express. Then it dawned on me…I have a Google mail (gmail) account (which can be configured as IMAP), so why can’t I set up my gmail server to send mail and thereby possibly bypass the firewall restrictions?

As it turned out, I could. First, I had to enable IMAP in Gmail. The steps are as follows:

1. Sign in to Gmail.
2. Click Settings at the top of any Gmail page.
3. Click Forwarding and POP/IMAP.
4. Select Enable IMAP
5. Click Save Changes

Next, I need to configure Outlook Express. I could have followed Google’s instructions on how to do this; however, I didn’t want to receive mail via IMAP, but just send  it. In order to do this, for each account I needed to send email from, I changed the outgoing server to imap.gmail.com. To do this:

1. Click Tools, Accounts
2. Select the account to change and choose Properties
3. Click the Servers tab.
4. Enter imap.gmail.com for the outgoing mail server.
5. At the bottom, check the box that says “My Server Requires Authentication”.
6. Click the “Settings” button.
7. Choose the “Log On Using” radio button.
8. Enter my gmail account name and password and click OK.
9. Click the Advanced tab.
10. Change the outgoing mail server to 465.
11. Check the “This server requires a secure connection” box.

With that, I was able to send email using Outlook Express, from behind the firewall.