In the extension Giveaways (Chat), when a giveaway is configured to allow N entries per user, then it is possible to enter up to 2*N-1 times.
Steps:
- Broadcaster uses
!setentries 5, then!rungiveaway - User does
!enter 4 - Same user does
!enter 5
Result: chat sees Thank you User for entering the Giveaway, you have -4 entries left. and user is entered 9 times (user is listed 9 times in the data\gaveaway\ListEntries.txt file)