I think I may have an amusing Outlook bug for you.
I call it "Future to the back".
1. Verify you use the latest Outlook 365 (may be relevant to other versions as well, I didn't try)
2. Go to the Calendar section
3. Use the keyboard combination of "CTRL+G" (Go To Date)
4. I use a date format of dd/mm/yy, so I typed 31.12.29 (or 31/12/29, . or / will do the same). Please do the same and submit. You will be transferred to the the last day of December 2029, cool, that's fine. It is just for reference
5. Now do almost the same, but this time type the next day of the day from above - type 1.1.30 and submit. POW…! You are now at the first day of January 1930…
It looks like any year submitted that is about 30, via 00 (2000) and until 22 will be in the range of 1930-2022, so the future for Outlook "Go To Date" command is only from 2022 until the end of 2029.