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One of my Outlook users having a strange behavior, as when she send meeting request to somebody, sometimes it reaches the other user as an email instead of a meeting request. She is using Outlook 2007 and the Zimbra Connector version 5.0.18_GA_3064_5.0.3066.
When Outlook can't parse the MIME, then we'll send it as an email. Many times this is a third party bug. A lot of times, there will be a local failure associated with this. Also, we did fix a bug in this area (bug 40298) which was fixed in a later version of 5.0.18 and then in 5.0.19
Premod, if you are running ZCS 5.0.13 and your user has the 5.0.18 connector, note that Zimbra doesn't recommend using newer connecters with older ZCS.
We are using the connector of 5.0.18 as per the suggestion of Zimbra only bcz it fixed some calendar issues especially.
Anyway I will have to upgrade my servers to 6.0, but again there are bugs reported for the upgrades. So waiting to get all fixed.