There are two main reasons why pumpkin rolls crack.  Make sure to follow the tips below to prevent it. One, the cake was too cold.  It's important to roll it up while it's still hot from the oven and to let it cool in the rolled-up state.  Otherwise, it won't be flexible and will crack when rolled. The other cause is the cake was overbaked.  A dried-out sponge will be brittle and crack much more easily.  Make sure to bake it just long enough for a toothpick inserted into the middle to come out clean (about 12-15 minutes at 350 F).