src/vs/platform/update/electron-main/updateService.win32.ts:272

• When restoring the Ready state after an Overwriting check fails, the explicit parameter passed to State.Ready should be the original explicit value from when the update was first Ready, not the explicit parameter from the current doCheckForUpdates call. The current explicit parameter represents whether the overwrite check was explicit, not whether the original update check was explicit. This should use this.state.explicit to preserve the original state.

					this.setState(State.Ready(this.state.update, explicit, false));

src/vs/platform/update/electron-main/updateService.win32.ts:272

• When restoring the Ready state after an Overwriting check fails, the instance variable this._overwrite should be reset to false to match the overwrite flag in the state. Without this, subsequent state transitions may incorrectly use this._overwrite = true even though we're no longer in an overwrite scenario.

				// If we were checking for an overwrite update and it failed,
				// restore the Ready state with the pending update
				if (this.state.type === StateType.Overwriting) {
					this.setState(State.Ready(this.state.update, explicit, false));

src/vs/platform/update/electron-main/updateService.win32.ts:381

• The optional chaining this.availableUpdate?.updateProcess?.once('exit', ...) on line 380 could resolve to undefined, causing the Promise.race to wait indefinitely. This could happen if this.availableUpdate or this.availableUpdate.updateProcess becomes undefined between line 377 (where pid is captured) and line 380. While unlikely due to the synchronous execution, if the method is called concurrently or if there's a race with another part of the code clearing availableUpdate, this could cause the timeout to always be hit.

A safer approach would be to capture the updateProcess reference at the start of the method (alongside availableUpdate), ensuring the same object is used throughout the cancellation logic.

					new Promise<boolean>(resolve => this.availableUpdate?.updateProcess?.once('exit', () => resolve(true))),
					timeout(30 * 1000).then(() => false)