Converting left-handers to their non-dominant right hand was previously widespread, particularly for handwriting. The present study aimed to explore the extent to which adult, converted left-handers can learn writing with their dominant left hand during a 2-year training program. Eleven converted left-handers participated in the training. Handwriting kinematics were assessed at regular intervals (seven sessions) and compared to those of 11 innate left-handed controls matched for age, gender, and overall handedness score for basic (Finger, Wrist, Circle) and complex (Sentence, Copy) handwriting tasks. Regarding basic tasks in the training group, we found rapid increases in left and right-hand frequency and no significant differences between both hands at any time point, indicating successful hand transfer. After 24 months, training participants significantly surpassed controls for writing frequency in basic tasks with their left hand. For complex tasks, we identified significant increases in the training groups’ left-hand writing frequency and duration between the first and last session. While training participants’ left-hand writing remained significantly slower than their right-hand writing, statistics confirmed final differences between hands only for the duration of the Sentence task. Importantly, left-hand writing in the training group was characterized by lower frequency, lower automaticity, and prolonged duration after 24 months compared to innate left-handers. With training participants’ left-hand writing skills significantly increasing for complex tasks and no final statistically significant differences between hands for frequency and automaticity, the program was considered effective. Nevertheless, within 2 years, training participants did not reach innate left-handers handwriting proficiency for complex tasks. Underlying reasons may be various, such as a non-optimal training program, a sensitive period for learning to write, irreversible neural changes during conversion in childhood, age-related decline of motor learning capacity, or retrograde interference between right- and left-hand writing.