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Hosted Outlook 2010 calendar sharing issue "Error while preparing to send sharing message"

He everyone,

I've got an issue that's going to need some advice.

Right now the problem is the we're having trouble sharing calendars through Outlook 2010.
I read that hitting the "to:" button and selecting the address from the global access list fixes the issue for most people... and in my case it solved the issue for exactly 1 of my users.
the rest all get a little bit further in the process before receiving a message stating "Error while preparing to send sharing message"

I've checked the calendar permissions, but i'm not entirely sure how it's to be configured -  do I need to add the users who this calendar will be shared with to the list manually for each calendar to be shared before I can try and share it? Also, I had to rebuild the active directory and recreate everyone's profiles at one point in time so it could be duplicate .pst/.ost files conflicting with things.

some more information: These mailboxes are hosted with out ISP (cbeyond) and they require a special patch to be installed for calendar sharing to work - I've insure this patch is installed on my test machines and hasn't changed anything to my knowledge. We do also have an instance of Exchange Server 2010 running on our local SBS2011 server that's supposed to be there to allow SBS2011 and Sharepoint Enterprise to send alert emails, is it possible that it's autodiscover settings are conflicting with the Calendar sharing settings of the Outlook 2010 installations on our domain?

Where do you guys think I should start troubleshooting this one? I can go into more detail about why I had to rebuild active directory and the install of exchange server if you guys think it might be interfering with the calendar sharing... but right now getting the employees the ability to share their calendars is my top priority.

Network Admin
Avatar of Manpreet SIngh Khatra
Manpreet SIngh Khatra
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Yep that did it for all the 2010 installations.

All the 2013 installations are still having the issue - but I still have yet to get a good confirmation from cbeyond as to whether or not their patch is compatible with 2013.

Thanks for your help!