Outlook Anywhere Authentication Issue NTLM/Basic


I have configured Outlook anywhere to run NTLM Authentication  but the settings on the local outlook keep reverting back to basic to which point Outlook stops working. I believe I have checked all the settings and look via the exchange command shell to which all have shown the correct NTLM setting.

Any ideas why the outlook client would keep reverting back to Basic Authentication

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Are the settings on the local Outlook being governed by a GPO? If so that would be where I'd start.
Dan130Author Commented:
Hi Jay,

I double checked by no GPO is controlling the local outlook config.
Dan130Author Commented:
any ideas on this ?
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Simon Butler (Sembee)ConsultantCommented:
Do an Autodiscover test from a client first:

See what is being returned to the client by the server.
How did you change the authentication settings? In EMC, EMS or IIS? Did you run IISRESET afterwards?

Dan130Author Commented:
Hi Simon,

I have changed the settings in the EMC and EMS, I didn't touch the IIS manager. I have not run an IIS reset recently on the exchange server. the settings appear fine in both EMC and EMS both are set to NTLM but something is setting it back to basic so user cannot then log in to outlook.

the results. I can see in XML it says <OWAUrl AuthenticationMethod="Basic, Fba">https://mydomain.local.

is this related?

ill continue to review your webpage linked but its their anything else to try.

Simon Butler (Sembee)ConsultantCommented:
No, that isn't correct.
When you run the test you should see a line for Outlook Anywhere.

It will say Protocol: Exchange HTTP and then further down Auth Package. That is what Exchange is configuring the client to use.

Dan130Author Commented:
ok thanks yes I can see that's the Auth Package is "unspecified" how would I go about changing this. if this is unspecified is this why it keeps reverting back to basic?
Simon Butler (Sembee)ConsultantCommented:
That is probably the problem - it hasn't been configured correctly.
Your best option here is probably to disable and then re-enable Outlook Anywhere. You can do that through EMC. However you must wait until the event log on the server reports that it has been disabled (About 15 minute after making the change in Exchange) before enabling it again.

Dan130Author Commented:
this is what I also got when using the command get-outlookanywhere
Simon Butler (Sembee)ConsultantCommented:
Do you have the RPC virtual directory in place?
It might be that there is an issue with IIS instead.
In that case, disable Outlook Anywhere in Exchange, wait for the event log.
In Roles and Features, remove the RPC Proxy component from IIS.
In IIS manager, remove (if present) the RPC and RPC-with-cert virtual directories.
Run IISRESET again.
Reinstall the RPC Proxy.
Finally enable Outlook Anywhere.

Dan130Author Commented:
Ok I have disabled outlookanywhere

removed the RPC proxy
run iisreset
I have removed RPC and RPC with cert as they were both present
run iisreset

are removing the role the server needs a restart during the day i will not be able to preform this on a live server, so will need to restart exchange install the feature and then enable outlookanywhere
Dan130Author Commented:
Followed as planned but still the issue persists. the issue does look related to IIS rather than EMC all of the correct settings are in place.
Simon Butler (Sembee)ConsultantCommented:
You are getting the same issue - the authentication setting is coming back as unspecified?
That is unusual, and would point at an issue with the IIS metabase. The only way I know to fix that is to remove IIS completely. That means removing the CAS role on Exchange first.


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