I was hoping someone here might have seen this problem before..

I am trying to upload my Outlook calendar into Google, with about 8
years of data.  Since i have > 20k entries, I need to break it up into
about 15 files to keep each under 1 MB.

I've chosen to break it up approximately be year or half-year.

The problem seems to be that repeating events in Outlook, saved as ICS
files, override each other when imported into Google.

That is, I import the 2005 file and someone's birthday comes up fine.
Then I import the 2006 file and the birthday only shows up in 2006 and
is deleted (in Google) from 2005.  Interestingly, if I then import
2004, it moves back to 2004 and deletes 2006.

This seems ridiculous to me - how do I import repeating events when I
have to break it up into so many files?

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