Best way to look at Outlook authentication failure

[PliotronX]

So am I missing something or after all the iterations of Outlook, 2013 still does not report any error and just asks for passwords when it is not in fact a password problem?

Also wondering if anyone is experiencing this with a multi-site setup without ADFS but with AD sync that is supposed to be automated with 365: users' passwords are expiring and after going through a change on their Windows 8.1 workstations, the password is not synchronizing with 365 even after two days while it is supposed to take place every 20 minutes (10 between domain controllers and another 10 to Azure IIRC). So far there are three confirmed cases, each at different sites, none are over VPN (site-to-site connections are via MPLS). The password appears to be "semi-syncing" where 365 does not accept the old password yet does not accept the one that the user entered when prompted at log-in to Windows. I have had to force a password reset within 365 which the higher-ups do not like but for expedience in getting the users their e-mail, the care meter is low. Strangely, the OWA does not accept the old nor new passwords either but the plot thickens because the users' phones are synced with 365! What I am irked about is why 365 is somehow receiving a corrupted password from AD. Any clues?

 

[imagoon]

Start Outlook, log in with all the prompts. Hold the control key and right click the Outlook icon in the tray. Open connection status and "test email auto configuration" to see where the system is connecting to. Most of the time the issue you are mentioning is a bad configuration esp if you migrated in to the O365.

If the domain names, certificates, OOF, OAB or any of the other URLs are pointing to the wrong servers you will see these issues. You then have to configure Exchange roles correctly.

Also I have used ADFS and not the sync tool, but I would imagine there are logs in that some place to verify the replication. I personally consider ADFS the preferred method though.

 

[PliotronX]

Start Outlook, log in with all the prompts. Hold the control key and right click the Outlook icon in the tray. Open connection status and "test email auto configuration" to see where the system is connecting to. Most of the time the issue you are mentioning is a bad configuration esp if you migrated in to the O365.

If the domain names, certificates, OOF, OAB or any of the other URLs are pointing to the wrong servers you will see these issues. You then have to configure Exchange roles correctly.

Also I have used ADFS and not the sync tool, but I would imagine there are logs in that some place to verify the replication. I personally consider ADFS the preferred method though.

OMG that Ctrl key trick is amazing, where has that been all my life? Thank you! We are prepping ADFS VM's but have not yet implemented it as we are also getting rid of the slow MPLS in favor of VPN over fiber. It turns out that one of the domain controllers went AWOL and was not replicating! Holy crap! Since I am not the one in charge of this particular network, I hadn't seen it but dang. Glad it was a limited headache, it had potential to be a major PITA.

 

[imagoon]

FYI with O365 remember these:

https://support.office.com/en-gb/ar...ook-2010-ce2b9143-ceca-48ac-bffc-c3059a4c5919

Esp the "/clean<something> and /reset<something>" ones since you can't do most of the fixes on the local exchange server with o365.

/rpcdiag is handy as it will pop the connection dialog up as outlook starts before it connects to anything.