Answer: There's no real trick to transplanting jade cuttings. Perhaps the potting soil is too moist? If you tend to overwater plants, try growing your cuttings in a cactus mix rather than regular potting soil. Cactus mix has sand and grit which helps it drain quickly. Or, it could be your timing. Jade has a need for a slight period of dormancy in winter, so reduce watering to once a month and no fertilizing during winter months from November through March.
Here's how I propagate my jade plant: Make a cut just below a node and put the cutting aside for a few days to allow the wound to dry completely. Then plant the cutting in a suitable medium and it'll take root.
Water liberally, depending on a finger soil test (checking for moisture one-half inch below the surface) but allow soil to become nearly dry between thorough waterings. Over-watering may encourage rot so water only when soil is nearly dry to touch. Remove any excess water after watering by preventing the pot from sitting in water.
Hope this information helps!
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