Following the release of the November update for Outlook, users are reporting that Outlook crashes when an iCloud calendar is subscribed as an Internet Calendar. (Calendars synced using the iCloud addin are not affected by this bug.)
The cause: the iCloud sends a gzip encoded response but Outlook is not expecting gzip. Outlook tries to decode it, but crashes because the response body is within a stream and not a buffer.
Microsoft is working on a fix, until then, use this work-around: go into File, Account Settings, Account Settings, and click on Internet Calendars and remove the iCloud calendar.
Outlook crashes on launch when you have an iCloud Internet Calendar in your profile (MSKB)
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