Apple Watch can't always reconnect

Resetting the wi-fi seems to do the trick.

The solution to the issue for me was to restart the computer

Always the same problem. Does not stop.

I submitted a report, but that sys file just kept saying "gathering..." for a long time, and I didn't see a reference number to offer

But, turning the WiFi off and on is working for me as well

I face this problem daily and have not found any way to fix other than building 1000 times and eventually it connects. I lose so much time over it, I really wish it would get fixed.

Any updates here? This is the first watch app I've built and it requires testing on a device and I'm simply unable to do it.

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...

Will this problem ever be solved? The Apple Watch was released in 2014 — it’s now 2025, and this issue still hasn’t been fixed. Maybe that’s why there are so few apps for the Watch: because the debugging process simply doesn't work properly.

I’ve been struggling with WatchConnectivity for three weeks. I need to use transferFile, but it doesn’t work on the simulator. I sit for 8 hours a day staring at the message: "Previous preparation error: Transport error."

Once in 200 attempts, Xcode might manage to launch the app on a real Watch — and even then, the connection drops within 10–15 seconds. Not a single one of the thousand workaround tips fixes the problem. Endless reboots of my Mac, iPhone, and Watch; switching Wi-Fi and Bluetooth — it’s all useless.

Maybe you could finally release a Watch that can be connected via a cable? Maybe that would solve the problem?

I've noticed this always happens when the watchOS updates. This error was happening continuously after a watchOS update, I restarted the computer, then all the shared cached symbols have to be slowly copied from watch to macos.

Now facing this problem as new Apple Watch developer. What a pain. Nothings helps. Restarted, put WIFI on mobile hotspot etc.