Calendar issues and read receipts

Hi all,
About 6 months ago we upgraded Exchange from 2003 to 2007 and from 2007 to 2013.
Server setup is Win2k12r2 with Exchange 2013 SP1.
Clients are all Win8.1 with Office 2013 up-to-date.
We have experience some issues from the start. But we are unable to resolve them.
Issue 1:
When Outlook is operating in cached mode and shared folders are downloaded too calendars shared between users are not up-to-date. This means: when a users adds an appointment to the shared calendar, it sometimes takes a lot of time before other users can
see this. We solved this issue by disabling the download of shared folders. This way all users work online in shared calendars.
Issues 2:
When using the above mentioned combination of a cached mailbox with online shared folders we are unable to use the context menu (right mouse button) on an appointment to set the category that is located in a shared calendar. The solution is to disable cached
mode in outlook, which means outlook is Online. Then the issue is resolved. But we would like to have outlook in cached mode.
Issue 3:
When outlook is in online mode the Read receipt function breaks down. When a user requests a read receipt (internally or externally) and presses the send button a message stating that the mail was deleted without reading is immediatly received. Putting outlook
in cached mode solves this issue. But it seems broken anyway but it might be a setting?
Any and all help is appreciated.

Regarding Issue 1, multiple users working off the same calendar risks race conditions, where one person's updates overwrite another's, and that problem is severely aggravated with the use of cached mode.  Please read the following two articles for more
information about your issues in more generality.
http://www.networkworld.com/community/blog/exchange-outlook-calendaring-problems-lost-me
http://www.networkworld.com/community/ExchangeCalendaringProblemSolutions
Regarding Issue 2, see my answer to above to understand why cached mode is bad for calendars unless they're used as read-only.
Regarding Issue 3, read receipts are unreliable.  If they work at all, consider it a little blessing.  Besides, they don't really prove the recipient read the mail, just that he opened it.  Read receipts are easily bypassed, so I recommend
you stop worrying about them.
Ed Crowley MVP "There are seldom good technological solutions to behavioral problems."

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