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Outlook 2016 Exchange 2010 autodiscover, multiple domains

My first time asking EE question

I have an Exchange 2010 server. External clients have been connecting to my server without issues via proxy https until they decided to upgrade to Outlook 2016. My clients domains are different than my own. I can connect myself externally, so I know our autodiscover is probably setup correctly. But my clients cannot connect

I put the following in Outlook 2016, works fine:
pli@mydomain.ca
my password

This does not work:
pli@myclient.ca
their password

https://mail.mydomain.ca/autodiscover/autodiscover.xml is accessible and returns the 600error message

I tried CNAME my client's on cpanel:
autodiscover.myclient.ca -> mail.mydomain.ca
I tried the XML regedit hard code with autodiscover.xml

On a side note, I've tried to do linked mailboxes because I read somewhere this can also solve my problem, but when I get to Trusted Forests or domains, it is blank even though I selected the database in the previous menu. Not sure where to go from here...
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Philip Li
Asked:
Philip Li
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1 Solution
 
IvanSystem EngineerCommented:
Hi,

what error do you get when you run Outlook Autodiscover and/or Outlook Connectivity on https://testconnectivity.microsoft.com/ ,for pli@myclient.ca ?

Regards,
Ivan.
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Lisa Hendrickson "CallThatGirl"MS Outlook ExpertCommented:
Honestly, I would downgrade the client to 2013 and do the manual setup. If you bought 2016 and cannot downgrade, let me know. I work with Outlook all day and 2016 is not easy to troubleshoot now that they removed the manual settings we all know very well.

And my reasoning is this, 2016 has many layers of issues with Exchange, on-prem and online. It breaks too often, not stable and while many might disagree with me on the downgrade, I found it the best and most stable for clients until 2016 catches up. I bill her hour and have spent hours fixing 2016 with frustration. I don't really see any major differences yet in 2013 vs 2016 and I tell clients when 2016 is stable, I will upgrade them.
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Philip LiAuthor Commented:
I get all errors for my clients domain autodiscover. Attaching photo, not sure how I can point their autodiscover to my domain autodiscover. I've tried CNAME as previously mentioned.

More and more clients get 2016 by default when installing Office365. One client insists on using 2016, so downgrading is my last resort.
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Philip LiAuthor Commented:
Btw, is there an option to downgrade to 2013 in Office365? Would help to get my clients going instead of using OWA
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Lisa Hendrickson "CallThatGirl"MS Outlook ExpertCommented:
Yes, it's not easy to find but under the 'install" area, look down below and it says "other installs" (which MS hates saying "downgrades" LOL)

Then you can select 32 or 64 bit. I do 32 usually.
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Philip LiAuthor Commented:
Thanks, I will temporarily try this to quell the storm. Still hope to get a server side solution to 2016 autodiscover.
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Lisa Hendrickson "CallThatGirl"MS Outlook ExpertCommented:
We all can hope they add back the manual settings :) I wish, dream and pray daily lol!
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Philip LiAuthor Commented:
Next best alternative to MS BS
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