Allowing Outlook 2016 through Smoothwall

[DNM]

Hi Guys,

 

We are using a smoothwall to filter our internet traffic for Staff and Students. We also use Office 365 for our email. We would like to allow our staff to use Outlook 2016 to Manage their email and Calendar.

 

This all seams straight forward so fare... Well it doesn't seam to work.. Every time we try and run the connection setup wizard it take and age to find the email server settings (fails), then tries and unsecure connection (fails) but if we uncheck the 'use proxy box' in IE it works first time.

 

Once outlook is configured, if you re-tick the proxy box Outlook continues to work perfectly with no issues.

 

Has anyone else had the same issue? Does anyone know of a solution to fixing this issue.

 

In our exceptions box we have the following;

 

*.ourdomain.org;*.office365.com;autodiscover-emeacenter.outlook.com;odc.officeapps.live.com;proxy.ourdaomin.local

 

Any constructive suggestion welcome.

[snagrat]

There was once a thing with Outlook 2013 that if you had the proxy server box ticked you had to ensure "bypass local addresses" box was unticked

 

Have you tried that?

[DNM]

Hi snagrat,

 

Yes I have tried with both Ticketed and Unticked hasn't made a difference.

[MatthewL]

Have you had a look here?

[nwkeene]

Hi DNM,

 

When i had issues with O365 and local exchange, it was the autodiscover entries in our DNS that weren't correct, once i'd done that, the Outlook autodiscover worked fine.

 

Also Outlook 2016 will only use a correctly specified autodiscover, you can't manually specify server settings...

 

My 2p

[DNM]

Hi Guys,

 

After a bit more digging around and a few checks, we have all the Authentication servers for O365 as Exceptions in our exception Policy. Both in IE and on the Smoothwall.

 

We have the autodiscover of autodiscover-emeacenter.outlook.com which is a C record on our DNS with autodiscover.school.org.

 

When we untick the proxy box Outlook 2016 is able to configure its self (finds the Autodiscover DNS and connects to the server) but when the proxy box isn't ticked it fails.

 

I have raised this with Smoothwall but don't seam to be getting anywhere with them.

[MatthewL]

Have you run a test using this?