For Square, adding a tip bigger than the order's total amount is possible. To do so, the order's amount must be higher than $1.10 dollar.
For example:
If the approved amount is $1, you can give $1 as a maximum tip to capture the final amount up to $2.
But if the approved amount is $1.10 or more, it is possible to add a tip that captures a maximum final amount of $400.
For example:
If the approved amount is $1.10, you can give a $398.90 tip with a final amount of $400.