Outlook 2007 not working using pfsense

[Inderpreet]

Hi,

I have setup PfSense in a small office and I have configure Squid, Squidguard and lightSquid over it. I have two big issues with it. Before explaining my issue lets understand how my setup is -

1. I am using proxy server ( ip 172.16.1.1) with port 3128
2. I have created users in proxy server
3. I have disabled the default LAN rule of PfSense( which allow full access to all users )
4. I have created a rule which explains that for 172.16.1.1 on port 3128 every request is acceptable .
Using this setting we are able to access the internet by putting proxy setting in browser and it asks for username and password and we do have that we have created in proxy server. Now the issue we are facing are as below -

1. We are not able to receive or send the emails in Outlook 2007 but when I re-enable the default LAN rule in pfsense it works fine.
2. We are not able to upload the Digital Signature over websites, like the tender websites where we need digital signature but if We re-enable the deafult LAT rule in pfSense it works.
3. Internet is very slow while using PfSense.

For more info let me explain the netwrok structure-

modem (pppoe) + Pfsense box + Router + all systems

I am sure there are some issues in the firewall LAN rules as everything works fine when I enable the default LAN rule in Pfsense. Please reply if someone have any idea wat to do.

[golmaal]

You need to create firewall rules to open the ports that Outlook is using.