Outlook 2013 not working, while outlook 2016 does

[mrbios]

I've just migrated all my users into office 365 and I'm trying to setup outlook so that staff just click outlook and away it goes.

 

I've got this GP enabled:

Automatically configure profile based on Active Directory Primary SMTP address

 

If i logon to a windows 10/office 2016 PC, it works fine, open outlook and your in within seconds

 

In office 2013 though i just get the error message "Cannot start microsoft outlook. Cannot open the outlook window. The set of folders cannot be opened. Your profile is not configured"

 

Prior to moving staff i just had an outlook shortcut pointing to a prf file, which worked fine, however as i understand it prf files + office 365 = no go.

 

I've got everything in place, registry keys and office updates, for modern authentication to work too.

 

Lastly these staff are logging on with mandatory profiles, there are no office/outlook settings within the profile itself. The only other GP enabled for outlook is "Do not allow an OST file to be created" this is the same for Office 2013 and 2016 though.

 

Any suggestions? I'm tearing my hair out!

[andydis]

can you manually create a profile and login successful?

Does your AD sync to 365 ?

[mrbios]

can you manually create a profile and login successful?

Does your AD sync to 365 ?

 

If i force outlook to open in safe mode and create a new profile it takes forever, then when searching for the user it fails to find the settings.

 

AD does indeed sync to 365, and that's working correctly. The user account in question is working correctly too, as displayed by outlook 2016 working nicely. I wish i could just replace outlook 2013 everywhere with 2016 but unfortunately i can't do that right now

 

EDIT: I lied in the OP, it's not a mandatory profile, it's a local profile...not that i think that matters.

 

EDIT:

Microsoft Outlook
Outlook cannot log on. Verify you are connected to the network and are using the proper server and mailbox name.  The connection to Microsoft Exchange is unavailable. Outlook must be online or connected to complete this action.
P1: 350569
P2: 15.0.4903.1000
P3: 
P4: 

 

That's my only event related to it, I'm going to try enabling outlook logging to get a better idea as to what it's doing though.

Edited April 10, 2017 by mrbios

[mrbios]

Ok this is frustrating, it appears there was an outlook.prf file in C:\Program Files (x86)\Microsoft Office and it was using that for the default profile. Deleting that file still doesn't resolve the problem though until i delete the profile manually from the mail settings and add in a new one again.

 

So...any idea where i go from here?

 

EDIT: From the looks of these, this office install was made with the customisation tool and the outlook settings were made within that....the only reason it has worked until now is due to the prf file that was replacing them.

 

Ok, possible workaround: I've deployed a registry delete policy to delete the HKCU key under outlook for the default outlook profile. Upon loading up outlook for the first time it creates the correct profile, however it pops up with an office 365 login box with the email pre-populated, i just have to click in the password box and it proceeds as normal (as we have SSO enabled on the passthrough authentication method) ... any way of stopping that box from coming up? Or possibly a cleaner method of getting rid of that default profile that's being created?

Edited April 10, 2017 by mrbios

[mrbios]

Ok, possible workaround: I've deployed a registry delete policy to delete the HKCU key under outlook for the default outlook profile. Upon loading up outlook for the first time it creates the correct profile, however it pops up with an office 365 login box with the email pre-populated, i just have to click in the password box and it proceeds as normal (as we have SSO enabled on the passthrough authentication method) ... any way of stopping that box from coming up? Or possibly a cleaner method of getting rid of that default profile that's being created?

 

Ok interesting one, the above fixes it, as does this:

Deleting the following HKEY_LOCAL_MACHINE\SOFTWARE\Wow6432Node\Microsoft\Office\15.0\User Settings\{6D3459CC-E1CC-4A5A-B8CF-6A674411302F} as that contains the importprf setting which is global to the machine, i think this is cleaner than the above as it forces the removal of prf settings for the machine, so i'll stick with that.

 

However I'm still getting office 365 login prompt (not a windows style login prompt, more of an mini internet window prompt) with the username predefined that just requires me to click sign in or click on the password box and it continues....my gut instinct is modern authentication not working correctly?

[mrbios]

Ok screw it i've gone back to ADFS, passthrough authentication just isn't quite true SSO yet it seems (or I'm doing something wrong and the internet has no answers....)

 

Using a shortcut i can now direct people at https://outlook.office365.com/OWA/?realm=domain.net and that sends them straight into their mailbox with no logon screen at all, as i had before, is there an equivalent path i can use to go direct to the office 365 portal rather than the mailbox?