Are you looking for push notifications or something like that?
Most iCal.ics-based calendars on the Internet suggest that they will be used in poll-like models similar to RSS or ATOM, in which the client will periodically check if any changes have been made and, accordingly, upload new content. I also understand that WebDAV-enabled servers may be able to allow some clients to directly modify these .ics files, but clients are still responsible for polling and updating their local calendar snapshot when they subscribe to it.
I donโt have much experience with Outlook calendar support for iCal, but I use Google Calendar, the built-in iPhone Calendar application quite widely, and I also used the Calendar Sunbird application in the past and they all work quite reliably, showing me updates when I check them .
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