Outlook is not working with squid proxy

5 pts.
Microsoft Outlook error messages
Proxy servers
Squid configuration
Hi i am having squid proxy server and with windows 7 home basic clients everything is working perfectly but outlook is unable to connect with gmail please help me thanks in advance

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I agree with Technochic and Carlosdl, more details r required.
Though, I am guessing (because I don’t have clear picture here) this is the problem related to NTLM authentication with Squid. Did u use NTLMV1…. Windows 7doesn’t support NTLMv1 by default. It is working in XP fine but not in Windows 7.
U can try out this….
Start > Run > regedit and find this
Now LmCompatibilityLevel, change it from 3 to 1
Now rebooting the computer.

CAUTION: Before do anything with regedit, it is a good practice to take proper backup of registry and if possible take care about important data !

Discuss This Question: 6  Replies

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  • Technochic
    What settings are you using to connect to gmail? Have you verified the correct server settings? What errors are you getting specifically when you try to connect?
    57,010 pointsBadges:
  • carlosdl
    More details could help. AFAIK Squid is not a pop/smtp proxy server, you would need to use something else (maybe iptables) and maybe Squid as transparent proxy. Can you describe your current configuration with more details ? Also, if you are getting errors, it could be a good idea to post them.
    85,885 pointsBadges:
  • CertifiedPCTech
    I am not sure as well but I am using squid via linux Suse ver 11 and I got squid configured for port 8080 and 80 as well. I am able to access all my webmail as well as my charter Email. I am wondering what kind of configuration are you using; did you setup any access list for emails and website.
    10 pointsBadges:
  • Sixball
    Not sure a regedit is the best first step - I'm more in line with Technochic in that the server settings for the gmail account should be the first place to begin looking...
    8,705 pointsBadges:
  • petkoa
    Don't bother about Squid configuration and authentication schemes if your webmails are working fine. Stick to Carlos' advice about iptables - login into SUSE box and check firewall configuration, then make sure smtp, pop3, imap, smtps, submission, imaps and pop3s (ports 25, 110, 143, 465, 587, 993 and 995) are allowed through the firewall - so to be sure all mail protocols will be working. Good luck
    3,140 pointsBadges:
  • CCProxy
    Gmail is different from other email service. The POP3, IMAP and SMTP (Port 465) are using SSL connection and SMTP (Port 587) is using STARTTLS connection. On the other hand, there's no STARTTLS option in Outlook Express. So if you want to send emails via Port 587, please use  MS Office Outlook 2007 (or above version) orThunderbird 7.0 (or above version).
    1. Create port map rules in suqid proxy
    2. Make mail proxy settings in Outlook Express for Gmail (POP3)
    3. Make mail proxy settings in Outlook Express for Gmail (IMAP)
    130 pointsBadges:

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