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EricFlag for United States of America

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using exchange server 2010 (on premise) clients randomly switch to office365 which breaks them

We had an issue where a failed upgrade from exchange server to 2013 somehow all exchange config data was deleted from the registry. I has been restored and all the issues that followed were manually fixed.  But one issues still remains.

when all the info was deleted devices all started to use office365 automatically. We had to delete hundreds of outlook profiles to fix this and get them pointing back to our on premise server.

What controls that?  DNS never changed. why is the outlook clients suddenly trying to go to office 365.  I cant seem to figure it out.

its worth noting that our Exchange schema is at 2013 due to the failed upgrade.
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Guy Lidbetter
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Hi Eric,

Could you be more clear about what happened?

What was the failure?
The registry on what servers?
Do you have Office365?
Are you doing Office365 testing (POC or Lab etc)
What are the devices and how do you connect in (Apple, Windows, Android?
The profiles on the phones needed to be deleted?
Do you have any MDM or just ActiveSync?

There really isn't enough information here for us to make any guesses.
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Jakob Digranes
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That's another question... when you say "devices"... do you mean mobiles, desktops or both?
"Started to use office 365" that is a very ambiguous sentence.. can you clarify how did it start to use office 365 ? You cant all of a sudden start using office 365..

You need synced accounts on Office 365 with Exchange license assigned to it and DNS properly configured or local DNS pointing to Office 365 servers.
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Guy,
I don't know exactly what went wrong. We hired consultants to help with the upgrade.  we had 2 2013 server roles installed, then decided we wanted to rename them. So he removed the server rolls.  Next thing i knew my mobile device and outlook clients were looking at onmicrosoft.com, our servers were unresponsive, and everything was hosed.  in ADSI edit we noticed the entire exchange node was gone.  It was a mess.
We since removed that guy from the project and put the upgrade on hold. after 40 hours of manually remapping mailboxes to users and recreating all our smtp alias.  

a sister company and us subscribed to office 365 and azure Ad. we do sync both our AD's to Azure.  (I was not really all that involved in office 365.  Its there but we don't use it. Nobody was ever automatically redirected to it through mobile or outlook until the outage.  
After fixing exchange and deleting outlook profiles clients automatically see on prem again.  then randomly later a small percentage of outlook clients are going back to onmicrosoft.com and we have to manually fix again.

Profiles on phones did not need to be re-deleted, but everyone had to follow our MDM instructions again once exchange was restored.  we have a 95% Android user base and leverage the azure solution Intune for MDM.
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Jakob,
I guess we have a Hybrid.  We switched to Office365 mostly for the per user office licensing with plans to eventually move exchange etc.  WE also wanted Azure AD.  WE have no near plan to move exchange to office365.  We are in the process in joining our sister company for Skype. We currently have on premise Skype, but they are using office365 Skype. We want to join them.  So I guess that's hybrid.

Outlook Client:
1) returns https://webmail.AdDomainName.com/Autodiscover/autodiscover.xml
now clients smtp addresses are not the ADdomain.  They are something a public facing domain name. We might have had SMTP addresses for the AD domain before the crash I dont know> we had to redo all SMTP aliases, They were not default but might have existed. That said their active UPN is the same as the SMTP address.

2-3) I get a login prompt for public domain, nothing for AD domain.

4)not sure how to test.

I don't see any autodiscover dns for the AD domain locally. I do see an autodiscover on our public DNS servers for our AD domain.
I Do see autodiscover DNS for our public facing domain locally and publicly.

I don't see any SRV record on the AD domain.
I do see a SRV record in the public domain.  though it points to an old Server FQDN that does not exist. I updated this to our current public domain name with the correct hostname.  name= _autodiscover domain= pubdomain.com  host was mail2.pubdomain.com.  changed to webmail.pubdomain.com

Sorry I did not follow your outlook test. All it did was open in safe mode.

Our office software is Office 365 installed locally.


Thoughts?
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Mohammed,
DNS does not point to Azure or office365 at all to my knowledge. That's why I don't get why outlook knows about it. (Publicly or privately).

Our division did not configure o365 so maybe it looks there by default if it cant see ours servers for some reason. I dont know why that would be true only after the outage.
Maybe its all related to our AD domain, and nobody having those SMTP addresses anymore?
The crash did not break Dns to my knowledge, so i don't think our AD domain ever had a autodiscover record.
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I was workign from home and noticed my desktop  at home which is not on the domain has not updated in a few days.  It said connected "updating folder"  but nothing was changing.  I have not been on this desktop in probably a week.

I closed it and reopened it and now my own outlook is doing it.
I have 3 emails and if i look at my account info it shows outlook.office365.com/owa/PubDomain.com/  :|

So i closed it connected to the vpn to see if it would go back, and i got this:

User generated image
Now it's hosed.
Hi

sorry for my late response.
Where does it say:    outlook.office365.com/owa/PubDomain.com/
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Jakob,
When i click, file account, my actual account switched. As i stated later i blew that profile away and its back to normal. But that is whats happening.  Outlook profiles are switching to the above at random.  Seems mostly or entirely people that are remote.
what's your public autodiscover dns record?
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autodiscover.pubdomain.com  In our publicly known domain namespace
autodiscover.ADdomain.com in our public Active directory domain name (old company name from many years ago. we never renamed our AD domain.

both point to the same public IP's
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additional note, in confirming this info. i noticed i had webmail.pubdomain.com set up as a round robin with our backup circuit.  I removed that host record and added it as a DNS failover option instead of round robin.  Seems like a longshot but the issues is spiratic, which could be such a dns issue maybe?
where did the 2 webmail DNS record point ?
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the same Ip as autodiscover.  I validated the NAT for those ips. It checks out.

I just noticed I cant get my mobile phone to hookup with exchange using the android outlook app.  It goes to o365 everytime.
so much for testing that :|
can you please test autodiscover or outlook connection from here;
https://testconnectivity.microsoft.com/ and post the entire result here
Hi Eric, any news on your case? :)
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I think this was unique to my weird environment of failed 2013 upgrade and improperly configured o365 licensing. removing the licenses seems to have fixed it.