Backdated runs

I have recently just joined this “site/community” and have about 2 years of data that needs to be transferred across. How long will this take? And will it all go across?

The amount of time depends on the service you connected to CityStrides. I’m unsure what that is, because you didn’t share your profile link.
Anything categorized as walking/running/hiking will make it into CityStrides.