Hello JamesonJendreas,
1. Check these important settings:
a. My outgoing server requires authentication (or Password or Challenge/Response for iMac)
b. Change the server timeout time from 1 min to 5 min
c. Uncheck leave a copy of email on server.
d. Try alternate SMTP port number: 25, 465, or 587. To send try using SSL and 587.
e. Change the outgoing server to smtp.googlemail.com
2. Do you have a firewall blocking the connection? Email virus checking? Popup Blocker? Temporarily disable them.
3. Update Outlook to latest configuration. Outlook 2000 should have SP3. Outlook 2002 should have SP3. Outlook 2003 should have SP2.
4. Use the Captcha verification to unlock your account
https://www.google.com/accounts/DisplayUnlockCaptcha5. See if the solutions here will help
http://www.slipstick.com/problems/nosend.htm6. You ISP may be blocking Gmail server. Use your ISP SMTP server.
Hope this helps!
war1