Configuring preferences and options in Outlook.com
I discovered the solution (as at April 2025):
- Click "Add Calendar" in the Calendar window
- Click "Upload from File"
- Browse to your ICS file and "open"
- Select a calendar to import to
- Click "import". You'll get a confirmation at the bottom of the screen.
They need to change the wording here. You would think this screen just adds calendars, not calendar items.