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can't configure outlook outside of network (outlook anywhere) and error in MS connectivity analyzer

I am unable to connect Outlook to a 2016 Exchange server from outside of the network. I keep getting prompted for a password even though I entered that during the initial config. Not sure if the info below is related but wanted to add it here.

When using the MS remote connectivity analyzer, I get this:
Attempting to test potential Autodiscover URL of this potential Autodiscover URL failed.
I also get the following failure:
The Microsoft Connectivity Analyzer is attempting to retrieve an XML Autodiscover response from URL for user Microsoft Connectivity Analyzer failed to obtain an Autodiscover XML response.
I think this is expected since this is testing against our third-party managed website not the exchange server. 

However, a little further down I get this:
Attempting to test potential Autodiscover URL of the Autodiscover URL was successful.
Everything below this in the analyzer passes / has green check marks.

We are migrating to Office 365 next week so started running checks and ran into this. Not sure if this can be ignored but if not, I am unsure how to fix it. Don't deal with Exchange servers much anymore.

Thanks for any help.
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Thanks, MAS. I will look it over. 
Everything was set as your article suggested. I went ahead and checked all steps. I did notice two certs attached to Exchange. One expired in 2020 and covered IMAP, POP, and SMTP (not IIS). The other Exchange cert is valid until 2022 and covers those plus IIS. I am going to remote into someone's computer and check the Outlook autoconfig. I still get prompted for a password during the setup of Outlook outside of the office network. When inside, no issues.

Any other ideas much appreciated. 
Please post the result of these commands.
Get-OutlookAnywhere | FT Identity,*auth* -AutoSize
Get-MapiVirtualDirectory | FT Identity,*auth* -AutoSize
Get-WebServicesVirtualDirectory | FT Identity,*auth* -AutoSize

Open in new window

Thanks a lot for the help. Results below.

[PS] C:\Windows\system32>Get-OutlookAnywhere | FT Identity,*auth* -AutoSize

Identity                          ExternalClientAuthenticationMethod InternalClientAuthenticationMethod IISAuthenticationMethods
--------                          ---------------------------------- ---------------------------------- ------------------------
InternalServerName\Rpc (Default Web Site)                               Ntlm                               Ntlm {Basic, Ntlm, Negotiate}
                              Ntlm                               Ntlm {Basic, Ntlm...

[PS] C:\Windows\system32>Get-MapiVirtualDirectory | FT Identity,*auth* -AutoSize

Identity                           IISAuthenticationMethods InternalAuthenticationMethods ExternalAuthenticationMethods
--------                           ------------------------ ----------------------------- -----------------------------
InternalServerName\mapi (Default Web Site) {Ntlm, Negotiate}        {Ntlm, Negotiate}             {Ntlm, Negotiate}

[PS] C:\Windows\system32>Get-WebServicesVirtualDirectory | FT Identity,*auth* -AutoSize

Identity                          CertificateAuthentication InternalAuthenticationMethods                ExternalAuthenticationMethods                LiveId
--------                          ------------------------- -----------------------------                -----------------------------                ------
InternalServerName\EWS (Default Web Site)                           {Ntlm, WindowsIntegrated, WSSecurity, OAuth} {Ntlm, WindowsIntegrated, WSSecurity, OAuth}
Since you are connecting from outside network do you have a third party SAN certificate like Godaddy?

Do you have SAN added in the third party cert?

Did you created a host A record in your public DNS for and pointed to exchange server public IP?

We are migrating to Office 365 next week  ?

Have your installed office 365 business version of Outlook 2016 on the computer from where you are configuring outlook?

If you have installed office 365 business version of Outlook 2016, then it will by default connect to Office 365 mailbox even though your mailbox resides in on-premise.

To fix this you need to create a registry entry on the computer for ExcludeExplicitO365Endpoint  and set to a value of 1. 
Hi Saif, thanks for the reply. I ended up installing a Code Two migration software in trial mode. I ran it and went through the wizard to configure my environment. Using Code Two it still failed but using the EAC for migration worked. The Code Two program was great and would've used it for the migration but when it didn't work but the EAC migration did, and since I need to be done migrating before June 1, I just ended up using the EAC.
My issue was resolved after using Code Two for the initial environment config. 
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