Outlook / Exchange Online / Office 365 auto discover

Hi All.

Here is an odd one.

Have an Office365 tenant.  Have created a mailbox on Office 365 directly (in cloud mailbox).

Office 365 testing shows all DNS records are Green - all entries as Microsoft requires, including autodiscover.

If I go to Office 365 webmail, i can access the new mailbox perfectly.  mailflow is fine.

If i start Outlook 2016 (which is fully patched etc), it fails.
- Establish network connection - fine
- Search for test.user@domain.co.uk - fine
- Then it pops up a login box, but Outlook is seeing this as an Internet email account

See screenshots.

I know the DNS settings are correct and I know the user/pass is correct (webmail test)

Have tried this on multiple different machines.  To no avail.  Both on the domain and not.

Here is the kicker...  Up until a few days ago, all working fine.

Pointers anyone?


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Jose Gabriel Ortega CastroCEOCommented:
Try it in here:
https://testconnectivity.microsoft.com/  (this will do the test externally)

And check your DNS settings, I know you said that they were right, but double check the record for autodiscover.

Also, you can open outlook then go to the "outlook icon" next to the time, press ctrl+right click and select the "autodiscover test" you can use that one too. (this will do the test internally or externally, depending on the location of the computer, this is o365 so will do the same test as the connectivity analyzer).
The screenshots don't show the "Internet email" designation.

When you type in the correct password, what happens?
JamieD71Author Commented:
Have run the test connectivity used the Office 365 "outlook connectivity" option.  It failed.  Everything green in the report except this at the bottom
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JamieD71Author Commented:
But if I run the Office 365 "Autodiscovery" test, then it's green (OK, haven't expanded it)

Tom CieslikIT EngineerCommented:
Check local DNS you try to setup outlook from

run CMD as Administrator

type nslookup

set typ=MX

then set type-TXT

Double check if all settings are correct and your DNS is see your External DNS setting for your email server correctly
JamieD71Author Commented:
Hi Tom.

Carried out the NSLookup tests and all as expected.  Also did a test of another domain on another tenant and that matches too.

Thank you

Jose Gabriel Ortega CastroCEOCommented:
So the external face is working.

Use outlook and post the log tab. (CTRL+right click the outlook icon next to the time) and select autodiscover configuration.

Add the user information en post the log tab content.
JamieD71Author Commented:
Hi Jose,

That's the problem - i cannot get the profile setup in Outlook at all.

When O2016 goes through the auto config process, it's like it's detecting the wrong type of account.  If you look at both screenshots on my original post, the 2nd one shows it's trying to detect the email account as "internet mail".  I personally have the same setup for myself and its working fine.  Same ISP/DNS provider, same settings (except for different domain names of course).


JamieD71Author Commented:
Fell foul of an autodiscover bug!!  https://support.microsoft.com/en-us/help/2212902/unexpected-autodiscover-behavior-when-you-have-registry-settings-under

Adding dword of ExcludeHttpsRootDomain  (value 1) solved it.

But Jose, you were on the right track - issues with autodiscover...

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JamieD71Author Commented:
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