New
#591
From my testing, there is definitely a limit on how many times you can transfer a digital licence to a new device (only three times) - in my tests I was using a digital licence upgraded from a retail licence. When it would not let me do it, I simply entered the retail key as normal and it activated - I then though perhaps the digital transfer count had been reset but no - still would not let me!
As far as I can tell, the digital licence does not carry the history of how it was created i.e. from an oem licence or retail. This is presumably why you can transfer a digital licence even if original was oem.
Whilst Windows still allows you to use original 7/8 retail key to activate windows 10, then none of this is is a problem. However, if and when they stop that (it will be interesting to see if CU version still allows old keys), then there will be some people who get caught with the limit.
Best advice I can give people if they install Windows on a new PC, try to use a product key first, as that sets up a new digital licence with transfer count set to zero. Only use the activation troubleshooter method when you have to e.g. you do not have a product key to save using up a valuable transfer count.