Early winter or late winter.
During dormancy, the cambium of juniper retracts and it's attached better to the tissue below. In active growing seasons like spring and summer, they separate more easily.
If your winters are wet and not that cold, consider using rubber/gummi tape/bicycle inner tyre. Raffia can hold a lot of water and it can activate dormant root tips on the trunk.. I've had a couple junipers produce roots on the trunk when I left raffia on. Some people remove it a couple weeks after they made their bends. I don't know how they do that.
I switched to rubber this year and I'm quite happy with how good it closes wounds by being flexible and pushing tissue back onto the trunk. Raffia wrapping takes some practice and when making extreme bends, it does create spots where there is little contact. I blame that entirely on my poor raffia wrapping skills, but with rubber I don't have that issue at all.