Hi McBean,
Thank you for sharing your question. I get how annoying it is when your calendar won't upload to Outlook, especially after you've tried everything.
It sounds like you're trying to see or import a calendar file (.ics) into Outlook, but you can't figure out how. That's a pain.
Usually, this happens because importing calendars is different on Outlook online versus the Outlook program on your computer. Some things, like importing calendars from the internet, are easier on the web version.
To fix this fast, use Outlook on the web (Outlook.com) or pick the right thing in the computer program. Here's how, made easy:
On Outlook Online
Go to Outlook.com or your work's web page and go to the Calendar.
Click Add calendar, then Upload from file.
Find your .ics file and follow the steps to import. This often skips the login problems you get on the computer program.
On the Outlook Program (Classic Outlook)
Go to File > Open & Export > Import/Export.
Pick Import an iCalendar (.ics) or vCalendar file (.vcs) and hit Next.
Choose the file from your computer and click Open as New to import the calendar stuff.
On the New Outlook on Windows
Open the Calendar, click Add calendar, and pick Upload from file.
Choose your .ics file and do what it tells you to import it.
If you're trying to add a calendar with a link (an internet calendar), pick From Internet instead of uploading a file. Then, paste the iCal link and sign up.
I hope this helps.
Best Regards,
Noel