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The time children spend with their parents affects their development. Parenting programs can help parents use that time more effectively. Text-messaged-based parenting curricula have proven an effective means of supporting positive parenting practices by providing easy and fun activities that reduce informational and behavioral barriers. These programs may be more effective if delivered during times when parents are particularly in need of support or alternatively when parents have more time to interact with their child. This study compares the effects of an early childhood text-messaging program sent during the weekend to the same program sent on weekdays. We find that sending the texts on the weekend is, on average, more beneficial to children’s literacy and math development. This effect is particularly strong for initially lower achieving children, while the weekday texts show some benefits for higher achieving children on higher order skills. Results are consistent with the hypothesis that the parents of lower achieving students, on average, face such high barriers during weekdays that supports are not enough to overcome these barriers, while for parents of higher achieving students, weekday texts are more effective because weekdays are more challenging, but not so difficult as to be untenable for positive parenting.