Exchange 2016 + Outlook 2016, external prompt see internal if not internet

membership

This solution is only available to members.

To access this solution, you must be a member of Experts Exchange.

ASKER

For the internal, I configured the internal ip but with an alias CNAME

Mail.domainets.fr> 192.xxxxxxxx

I have to check.

When I go outside, the connections are random, it works, sometimes it disconnects, oddly If I make a profile, it works, and can lose the connection sometimes .. if I close outlook and reopen it asks for the identifiers of Connection is not really normal from the outside either.
Yet I check the box "keep my identifiers" in outlook.
The credential manager, deleting etc .. does not change anything.

We have a proxy Sophos... (?)

SOLUTION

membership

This solution is only available to members.

To access this solution, you must be a member of Experts Exchange.

ASKER

Yes it is an internal proxy.
Precisely I ask myself the sophos proxy questions. Because external and internal authentication for all services is in NTLM (or negotiate)
But why outlook constantly asks for authentication?

We'll look for the firewall, but the owa and the rest are accessible from the external.

Here is for example what it gives (from outside)
I open outlook and it asks me for authentication

If I type the password

I close outlook and reopen

I also noticed that the offline address book OAB does not download

SOLUTION

membership

This solution is only available to members.

To access this solution, you must be a member of Experts Exchange.

ASKER

For the outside, ok, but how in this case did not asked for authentication at each opening or randomly?

SOLUTION

Radhakrishnan

membership

This solution is only available to members.

To access this solution, you must be a member of Experts Exchange.

ASKER

Hello, ok thanks i will do the tests. In the meantime I will also see if the Sophos proxy server does packet inspection
The outlook anywhere is configured with the external address in mail.domain.fr in NTLM. Do you think I should switch to basic?

thanks, thanks for help

ASKER CERTIFIED SOLUTION

Radhakrishnan

membership

This solution is only available to members.

To access this solution, you must be a member of Experts Exchange.

ASKER

Ok for NTLM, but it goes in contradiction with what says Amit Kumar not?

The exchange is live, (no TMG / ARR / ISA etc ...))

Logic, NTLM for internal clients
Basic for external OA (?)

No Manu, I also said same thing that computer/user connected to domain network will not have to enter creds for NTLM. but for external network it will ask.

Now comes with Internal authentication prompt, which I already said that if Proxy is routing this traffic then it should not because it is internal traffic Proxy is required for internet traffic.

ASKER

Ok, understood, thank you very much.
I'll look at the proxy and if necessary make changes for authentication.
Thank you well, I keep you up to date :)