On watchOS, the Developer Mode entry under Settings -> Privacy & Security is hidden by default and only appears after Xcode has attempted to connect to the watch as a development device. In my case, once Xcode triggers that surfacing, opening Settings -> Privacy & Security on the watch prompts for a 4-digit Screen Time passcode before granting access. No Screen Time passcode I set on the paired iPhone is accepted at this prompt, which prevents me from reaching the Developer Mode toggle to enable it. The passcode prompt only appears in this specific state. With no Xcode connection attempt (and therefore no Developer Mode entry surfaced in the menu), Settings → Privacy & Security opens normally on the watch with no prompt at all. Environment macOS: Tahoe 26.4.1 (Build 25E253) Xcode: 26.4.1 (24909.0.3) (Build 17E202) iPhone: iOS 26.4.2 Apple Watch: Ultra 3 running watchOS 26.4 All devices on release software (no betas). Xcode error Developer Mode disabled Domain: com.apple.dt.deviceprep Code: -28 Recovery Suggestion: To use [Watch Name] for development, enable Developer Mode in Settings → Privacy & Security. User Info: { DVTErrorCreationDateKey = "2026-04-30 09:38:57 +0000"; "com.apple.dt.DVTCoreDevice.operationName" = checkDeveloperMode; } Reproduction Pair Apple Watch to iPhone (paired fresh, set up as new, not restored from backup). Connect iPhone to Mac running Xcode 26.4.1. Before any Xcode connection attempt, open Settings -> Privacy & Security on the watch. The menu opens normally with no passcode prompt. There is no Developer Mode entry visible. In Xcode, attempt to use the Apple Watch as a run destination. Xcode returns the -28 / Developer Mode disabled error above and instructs me to enable Developer Mode in Settings -> Privacy & Security on the watch. After this attempt, the Developer Mode entry is surfaced in Settings -> Privacy & Security on the watch. Open Settings -> Privacy & Security on the watch in this surfaced state. The menu now prompts for a 4-digit Screen Time passcode before allowing access. The passcodes I have set on the paired iPhone are rejected. The passcode prompt is therefore conditional on the Developer Mode entry having been surfaced by a recent Xcode connection attempt. In step 3 (no surfacing) the menu opens freely; in step 6 (surfacing in effect) the menu is gated. What I have already tried Confirmed Screen Time is disabled on the paired iPhone. Confirmed Share Across Devices is enabled. Confirmed Content & Privacy Restrictions is off on the iPhone. Confirmed I am an adult in my Family Sharing group (not a managed/child account). Confirmed there are no configuration profiles installed (Settings -> General -> VPN & Device Management is empty). Set a fresh Screen Time passcode on the iPhone. Not accepted by the watch prompt. Used Forgot Passcode? → Apple ID authentication to reset the Screen Time passcode and set a new one. Not accepted by the watch prompt. Turned the Screen Time passcode off entirely on the iPhone. The watch still prompts for one when Xcode is connecting. Unpaired the Apple Watch and re-paired as new (not restored from backup). Issue persists. Tried entering the watch's own device passcode at the prompt. Not accepted. Question What credential is the watch's Privacy & Security menu actually checking against once the Developer Mode entry has been surfaced, and how can it be reset or cleared from a paired iPhone? Is anyone else seeing this conditional gating where the menu is only locked in the post-surfacing state? Any pointers from the Xcode / watchOS tools team would be appreciated. Happy to provide sysdiagnose or further details on request.