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The alerts involve the in-game calendar, so
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The calendar is LoadOnDemand so won't actually be loaded and it's functions/data available until after the user clicks the calendar button.
You could try at PLAYER_ENTERING_WORLD:
Code:
if not IsAddOnLoaded("Blizzard_Calendar") then
UIParentLoadAddOn("Blizzard_Calendar")
end
--- Your code goes here