Loosen the mascarpone: In a large mixing bowl, add the mascarpone cheese and about ¼ of whipping cream. Whisk until the mascarpone is very creamy and thinned out.
Whip the cream: Add the rest of the whipping cream, espresso powder, and vanilla extract. Whisk vigorously until it becomes firm peaks.
Fold in condensed milk: Slowly pour the condensed milk into the whipped cream while folding it all together with a spatula until no streaks of condensed milk remain.
Add ladyfingers: Crumble the ladyfingers into small pieces and fold them into the whipped cream mixture until distributed.
Fill pan: Pour the mixture into a loaf pan. Use a fine mesh sieve to dust the top with cocoa powder.
Freeze: Cover and freeze the ice cream mixture for at least 6 hours or until firm. When scooping the ice cream, let it sit at room temperature for 10-15 minutes. Run an ice cream scoop under hot water before scooping.