I'm developing using my old Series 4 and experienced similar issues: endless "transport failures", connection issues, connection drops, etc. What you need to understand is that all those issues are likely to be caused by your wifi infrastructure. For example: Series 4 can only connect to 2.4GHz wifi... while your Mac and/or phone can do both 2.4GHz and 5GHz. The thing is that in more and more places, both networks are joined under a single hotspot name... My Optimum ISP even calls this "SmartWiFi". Well, let me say that: there is nothing smart about it. On paper, your MacBook, phone, and watch are connected to the same network, but in fact, some of them could be on 2.4 and others could be on 5GHz networks. Thats what always causes those issues with debugging. If you have a similar situation, you need to ask your ISP or network administrator to separate 2.4 and 5GHz networks into different names and make sure all your devices connect to the same network. In my case I connected everything to 2.4 and haven't had connection issues ever since. There is also a workaround if you work in a public space where you cannot do anything about it. The solution is to use your phone as a hotspot and manually tell your watch and MacBook to connect to it. Hope that helps...