Delegates don't always receive calender invitations for their boss when they are also invited

We have an executive who has two people that manage his calendar.  They are both Delegates and both receive his calendar invitations.  He does not receive them in his inbox at all.

Recently, both have complained of multiple instances where both they and the executive are sent a calendar invitation for a call/meeting/etc.  However, only the invitation for them appears in their inbox.  The invitation for the executive is not displayed, and the meeting/call does not show up as 'tentative' in his calendar.

This only happens about 10% of the time, but it is enough to cause problems.

I don't even know where to start looking here.

The executive is running Outlook 2007.  One assistant is running Outlook 2010 and the other is running Outlook 2007.  We have Exchange 2007.

Thank you.
Christopher BeaugrandCIOAsked:
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Christopher BeaugrandConnect With a Mentor CIOAuthor Commented:
Turns out that the delegate part of this was not the issue.  Opening a new question now that I have additional information.
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AmitIT ArchitectCommented:
Upgrade all to same outlook version. Then test the result. I have seen same issue, due to outlook version issue.
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Christopher BeaugrandCIOAuthor Commented:
As you can imagine, that's a bit easier said than done.  I will try that when possible.  

Anyone else experienced this particular issue?
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Christopher BeaugrandCIOAuthor Commented:
With new information, the question is no longer accurate.
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