Wildcard not working, and some pdf redirects

Hi,

I need to redirect all references to /meetings/board/(.*) to /board-meetings/ (clicking regex)

I’ve tried it that way, but also /meetings/board/board_meeting.asp to /board-meetings/ and
https://mysite.com/meetings/board/board_meeting.asp to https://mysite.com/board-meetings/, which it automatically shortens to /meetings/board/board_meeting.asp to https://mysite.com/board-meetings/. None of these are working, but there are plenty of other redirections that are working.

Another strange thing is that most of my pdf redirections work, but some do not.

How do I troubleshoot both issues?

Thx.