Definitely a hell of an experience in the worse way. Apple Watch Series 4 iPhone 11 Mac Neo I had 0 issues developing/deploying to Pixel WearOS, but obstacles after obstacles, developing for and deploying to Apple WatchOS. After several days of working around each obstacle with the help of Gemini, I'm adding the summary of what I had to do so far to get to initial deployment in case this helps Apple/others with fix/workarounds: Here is the complete technical post-mortem for the development environment setup. This summarizes the specific hurdles cleared to get a Watch Series 4 (watchOS 10.6.2) communicating with your Mac via a No-SIM iPhone bridge. 🛠️ Environment Recovery Summary The Networking Layer The primary blocker was extreme network instability on the default 10.0.0.x gateway. The Symptom: ping tests showed 62% packet loss and 1,000ms+ latency. The Fix: Migrated all devices to a clean 192.168.86.x subnet. The Result: Achieved 0% packet loss and ~13ms latency, providing the stable "pipe" required for the cryptographic DDI handshake. The "Physical" Overrides (Critical Breakthroughs) Even with a good network, the Series 4 hardware required specific environmental states to stay "Ready": Bluetooth Disabling: You had to turn off Bluetooth on the iPhone. This forced the Watch to stop trying to tunnel through the low-bandwidth Bluetooth LE connection and instead use its internal Wi-Fi radio for a direct high-speed link to the Mac. The "Puck" Requirement: The Watch had to be left on the magnetic charger. On the Series 4, watchOS 10 aggressively throttles the Wi-Fi chip to save battery; the charger acts as a "High Performance Mode" toggle, keeping the radio active for the 500MB+ disk image mount. Security & Software Gatekeepers Since the Watch had been recently reset, several security "flags" had to be manually toggled: Passcode Enforcement: You set a 4-digit passcode. watchOS 10 often refuses to mount a developer partition if the "Secure Enclave" isn't active. Developer Mode Loop: You performed a "hard refresh" of the Developer Mode toggle (Off -> Restart -> On -> Restart) to force the Watch to re-provision itself on the new subnet. Daemon Flush: We cleared the "zombie" states on the Mac by killing remotepairingd, remoted, and flushing the CoreDevice cache in ~/Library/Developer/. Additionally, I had to unlock 100's of times both phone and watch and keep the watch in wake state. Oh, I ended up purchasing a Neo since the MBP 2015 was out of support and expect to spend $99/y for Apple Developer Program. Compared to one time $25 Android Development Fee and nothings else. Also, I've been able to get Claude to build/deploy on AndroidStudio via CLI but many steps needed to be done manually on XCode. For context, I started my Google/Apple phone/watch development journey last month at the same time and feel the need to convey the differences in developer experience between platforms. I'm looking forward to closing the gap, Apple.