Many tasks require humans to manipulate dynamically complex objects and maintain appropriate safety margins, such as placing a cup of coffee on a coaster without spilling. This study examined how humans learn such safety margins and how they are shaped by task constraints and changing variability with improved skill. Eighteen subjects used a manipulandum to transport a shallow virtual cup containing a ball to a target without losing the ball. Half were to complete the cup transit in a comfortable target time of 2 s (a redundant task with infinitely many equivalent solutions), and the other half in minimum time (a nonredundant task with one explicit cost to optimize). The safety margin was defined as the ball energy relative to escape, i.e., as an energy margin. The first hypothesis, that subjects converge to a single strategy in the minimum-time task but choose different strategies in the less constrained target-time task, was not supported. Both groups developed individualized strategies with practice. The second hypothesis, that subjects decrease safety margins in the minimum-time task but increase them in the target-time task, was supported. The third hypothesis, that in both tasks subjects modulate energy margins according to their execution variability, was partially supported. In the target-time group, changes in energy margins correlated positively with changes in execution variability; in the minimum-time group, such a relation was observed only at the end of practice, not across practice. These results show that when learning a redundant object manipulation task, most subjects increase their safety margins and shape their movement strategies in accordance with their changing variability.