An electronic device such as a wristwatch may include a housing with a dielectric rear wall. Wireless circuitry in the device may include an antenna formed on or over the rear wall. Matching circuitry may match the impedance of the antenna to the rest of the wireless circuitry. Processing circuitry may gather receive signal strength information and/or phase and magnitude information from radio-frequency signals received through the rear wall. The processing circuitry may track the position of the device and accumulate user statistics over time. The processing circuitry may determine whether changes in loading of the antenna through the dielectric rear housing wall have occurred based on the receive signal strength information, user statistics, and/or phase and magnitude information. If a change is detected, the processing circuitry may adjust the matching circuitry to mitigate any potential antenna detuning as a result of the change.