Smoothwall and Exchange 2007 with Full Outlook 2010 client issue

[_techie_]

Hi,

 

We have a smoothwall box which seems to be working correctly as it should with regard to our web-filtering.

 

We have our in-house hosted Exchange 2007 server which has an external address of www.bitcoinmerchandise.com | buy stuff with bitcoin

When running Outlook 2010 client when using our smoothwall proxy, whenever Outlook client runs it prompts for username and password, even if the remember credentials box is checked. This is on Windows 7 btw.

 

If using our "techie" non-smoothwall proxy, this issue goes away, and it is commonplace on our admin computers which run the full outlook client (not OWA) whilst using smoothwall as a web-proxy.

 

I have tried adding numerous proxy exceptions to the users, including the IP of the exchange box, the local hostname, and the external address, all with no luck.... We do have auto discovery off, which I think might be linked to the problem, but we cannot run this anyway, as we are behind our county council corporate WAN firewall.

 

I am sure this is some configuration issue with smoothwall that can be resolved - can I put some sort of proxy exception into smoothwall for this or is it something else.

 

I have tried in outlook settings to turn off "Encrypt data between client and Exchange Server" but this didn't seem to do anything either.

 

Can anyone help?

 

Thanks

_techie_

[DT2]

Are you using SWG or UTM?

 

DT

[_techie_]

Smoothwall Guardian - (SWG)

[DT2]

And G3 or G2?

 

DT

[_techie_]

G3 from what I am reading here on the smoothwall admin...

[DT2]

You could try adding your exchange IP to the destination exceptions list under Guardian>Web Filter policies>Exceptions.

Is the SWG set as default gateway for your clients?

 

DT

[_techie_]

Tried the destination exceptions...no joy.

The default gateway is currently set to the router address (10.57.4.1), not smoothwall (10.57.4.3)

Is this the problem?

 

Thanks,

Mark

[DT2]

No, I don't think so.

the outlook traffic shouldn't even be hitting the smoothie as the server is internal.

Could you Pm me a rough diag of your setup?

 

DT

[_techie_]

You have PM - Thanks

[sukh]

Can you explain how Outlook connects to Exch, ie. is Outlook>Proxy>Exch?

[_techie_]

Can you explain how Outlook connects to Exch, ie. is Outlook>Proxy>Exch?

 

i am not entirely sure, but you can still connect to the exchange box when in school, without a proxy set at all.

However, this is unfeasible, since the users will no longer have any internet access!!

This issue is now resolved though, with thanks to DT.

 

Thank you!

[sukh]

Curious, was it an Exch config?

[DT2]

No, not at all. You have to set an authentication exception on the smoothwall for the exchange server.

 

DT