Error while preparing to send sharing message (Outlook 2007/2010/2013/2016)

I got the following error when I had migrated a customer from a Small Business Server to our local Hosted Exchange.

Outlook on a domain looks to Active Directory to get the auto discover information. If you run the Outlook connectivity tester on the affected computer, you will see that it returns the local SBS server autodiscover settings, even if you have configured Outlook to use an external provider.

The simplest way to fix this if the SBS server is still in used and Exchange is still installed, is to run the following commands:

Get-ClientAccessServer | Set-ClientAccessServer -AutoDiscoverServiceInternalUri https://mail.externaldomain.com/Autodiscover/Autodiscover.xml

And

get-autodiscovervirtualdirectory | Set-AutodiscoverVirtualDirectory -ExternalUrl https://mail.externaldomain.com/Autodiscover/Autodiscover.xml -InternalUrl https://mail.externaldomain.com/Autodiscover/Autodiscover.xml

This then points the Outlook client to the correct external Autodiscover service.

If you have any questions, please let me know.

Outlook cached mode can cause problems…

Have you had the problem where Outlook sits there, forever, waiting to “update current folder”. I recently had this problem when changing an Outlook 2007 client to HTTP over RPC. After I made this change, weird stuff started to happen. No problem I thought. I will use scanpst.exe and attempt to scan the file. In the past, this has been where most of these sorts of problems lie. This was quite a large file, 3.5gb. After this had completed and still didn’t work, I started scratching my head a bit. What would cause this to happen?

After a bit of testing, I found that turning cached mode off let the folder update. I then proceeded to delete every file out of the Outlook folder (under local settingsapplication datamicrosoftoutlook) apart from the ost file and archive folders.

This fixed the problem. This is the first time I’ve come across this so I thought I’d share.