Ms outlook not working behind pfsense - need help

cgprasad

hi johnpoz

In-spite of adding the any any default allow rules at the top of the rules, doesnt help my outlook access the pop.rediffmailpro.com as well as smtp.rediffmailpro.com

I don't understand whether its the issue of the rules or squid. I'm able to access the web-sites though, with all the squidguard filtering active.

Also, i noticed that my antivirus doesnt take any updates too.
so basically its like my web browsing is fine, but any other application isn't being able to access the internet behind pfsense.

i'm using 3128 as the proxy port in my web browsers.

Thanks.

Supermule

Yes. Have you configured your LAN settings on the PC's to use 3128 as proxy as well??

If its only your webbrowsers then Outlook doesnt have a clue that you use proxy.

cgprasad

yes.

i've configured my web browsers to use the proxy port as 3128 , and that how i'm accessing the internet so far, with squidguard filters active.

Its just that outlook isn't able to connect to my pop and smtp servers. precisely the servers are pop.rediffmailpro.com and smtp.rediffmailpro.com

what ive also noticed that from my client pc's i'm unable to ping the ADSL router ip (192.168.2.1) , but i can ping the WAN ip (192.168.2.2) which is directly connected to the ADSL router.

any luck!!

dashboard.png_thumb

johnpoz

^ exactly if your using a proxy you need to tell your applications to use the proxy.. Your transparent mode proxy only works on web ports I believe, I do not believe it works on non 80/443 ports.

I don't use the proxy in pfsense for many years.. I don't see the point in a home setup.. Unless you have kids you need to filter from bad sites, etc. Yes back in the day when my sons were teenagers filtering porn was a common task ;)

So either have outlook use your proxy or rethink your need of proxy in a home setup - is this a home setup?

cgprasad

hi
I'm using pfsense in a small office setup , where ,my primary requirement is to block web based email access. Hence i'm bond to use outlook client for my pop and smtp servers hosted on the my webspace (ISP) provider. The email service provider is rediffmailpro.com

I'm NOT using TRANSPARENT mode of squid. I'm using the port 3128 (configured in my browser) to access the internet.

Do you mean to say that i need to configure squid in TRANSPARENT mode inorder to make other application such as outlook and antivirus software get connected to the internet?

also, there's no setting as such in the outlook client to configure it to use a proxy. It takes the settings from Internet Explorer browser itself.

Hope there's a solution to this.

Thanks All

johnpoz

If you using in explicit mode - then configure your client vs relying on auto anything..

But if your not using transparent mode then anything not set to use the proxy should just go out the normal firewall rules and should work.

So you have any any rule currently - tell outlook NOT to use the proxy and does it work then? If so then you can configure the correct firewall rules to work and you will be good

cgprasad

hi

the issue is this. Outlook doesn't have any settings for proxy setup. It uses the setup provided by IE (browser).

i've decided to re-install pfsense and try this all over again. Actually a bit fed up with tweaking it for past one week.

Thanks

johnpoz

And you can tell outlook NOT to do that!!!

cgprasad

i need to check that.

meanwhile i tried changing my email client from outlok to thunderbird. The best part is thunderbird has a settings for proxy, but when i configure it, and try to acces my mails, i see no errors , but even i don't see any mails popping and mails are not going out too.

So i decided to re-install pfsense all over again with squid and squidguard + lightsquid

Do you thin that SQUID has to be configured in Transparent mode for this thing to work?? I guess not. Let me try again and revert.

Thanks

johnpoz

Ok - so outlook 2007, I can look when I fire up my work laptop. But from quick google guess it has no proxy settings. And only uses IE setting, but only for http.

So that being said - if your lan rules allow the traffic it should work.

Tell you what – if you setup a test email account for me to play with, more than happy to work out what you need to do. Just PM me the details. I wont be sending more than a couple of test emails to validate it works. And then you can kill the account.

I don't have any problems firing up squid for testing, etc.

cgprasad

what details you need?
I'll be onsite from 11am IST.

Let me know.

thanks

johnpoz

Just need login info for a mailbox on your server. I can then behind my pfsense validate access using outlook 2007 and setup squid on my pfsense and work out what your doing wrong, etc.

so from looking at my outlook 2007, the only proxy support it seems to have is when connecting to an exchange server using http/https - under the connections section outlook anywhere.

If you are using proxy that prevents access directly out and only the proxy can connect out then you would need to setup your proxy to handle the connections on the ports your using and point your email client to the PROXY for server settings, pop, imap, smtp etc. And then setup the proxy to connect to your outside server.

I could test with using something like my google account with outlook - but would be better to use an actual account on your server so I can figure out exactly what your using be it pop or pop over ssl or imap or imap over ssl, be it you have to auth to your smtp server first before sending mail, etc. etc..

cgprasad

thanks for such overwhelming response.

I re_installed pfsense and my outlook started working . I guess there were some issues with the defaults rules. Also i had installed 2.0 , but now installed 2.1 version.

Thanks again.

johnpoz

no the default rules would allow ALL traffic.. From what I can tell is you removed the default rule and were creating your own, etc.