My Autorank is set up correctly, to my knowledge, and when a player types /ar check, it says:

has played for 6 days 9 hours 25 minutes and is in Guest.
Requirements to be ranked up:
meets all the requirements for rank Member but has no (new) rankup.

Settings:
use advanced config: true

Advanced config (spaced correctly):
ranks:
Guest:
requirements:
time:
value: 10m
results:
rank change: Member
message: 'Congratulations, you are now a Member!'
Member:
requirements:
time:
value: 48h
results:
rank change: Normal
message: 'Congratulations, you are now a Normal!'

(I receive no errors in game or on console upon reloading the plugin.)
I don't understand whats incorrect?

It seems the player has already been ranked to the member group before.

So would resetting the playerdata.yml fix that?
Also, I'm trying to keep the data from another server, So I transferred all the times in the Data.yml, if so, should I also transfer the playerdata.yml to keep everyone at the ranks they were?

If the ranking ladder and groups are the same on the other server, you can transfer the playerdata. Otherwise, I would suggest resetting it. Tomorrow I'll add an option to disable the blocking of ranking when a group has already been ranked to.

oh I see what you mean, in an older version of Autorank, I was used to it just ranking you up, no matter if you had been ranked up to the same rank before.