Here is the portion of your regex which actually consumes the input:
[A-Za-zd$@$!%*?&].{8,}
This means that the password must start with one of the characters in the above character class. It also means that a valid password must have nine or more characters, because the class counts for one, and {8,}
means 8 or more. So the following would fail because it does not begin with any such character:
1oB!gb0s5
The second example you gave fails for a different reason, because it only has 8 characters:
Pass@123
I don't know exactly what logic you want here. If you just want to ensure that a password has a lowercase, uppercase, number, and special character, then maybe you can remove the leading character class and just stick with the lookaheads:
(?=.*[a-z])(?=.*[A-Z])(?=.*[0-9])(?=.*[$@$!%*?&]).{8,}
Here is a demo which shows that your two example passwords would pass using the above pattern.
Demo