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Hi Chris, unfortunately this is an existing issue when a webinar is scheduled as a series with a custom schedule instead of a regular recurrence. If the webinar sessions are scheduled for every Monday etc, Outlook will accept it. If the webinars are scheduled for irregular days and times Outlook doe not accept it through. If you try scheduling a recurring meeting in Outlook for example, you will see that it only allows sequential recurrences.
This is Karen, the originator of this thread - I am using Outlook 2010 (MS Office Professional Plus 2010, version 14.0.7151.5001 32-bit). I have not tried adding a series webinar since posting; what I'd gotten at that time was a single entry on my calendar, where the contents had all the dates and links. I had to manually create each future date and paste the contents into each.
I think I remember having this problem before and the issue was it could only add all the sessions if you used a very regular schedule. One that had a 'recurrance pattern' that Outlook would recognize. So something like "every Monday" or "monthly on day x of the month"....
It worked great once we adjusted to that.