Acoustic signals play a fundamental role in avian territory defence and mate attraction. Several studies have now shown that spectral properties of bird song differ between urban and rural environments. Previously this has been attributed to competition for acoustic space as a result of low-frequency noise present in cities. However, the physical structure of urban areas may have a contributory effect. Here we investigate the sound degradation properties of woodland and city environments using both urban and rural great tit song. We show that although urban surroundings caused significantly less degradation to both songs, the transmission efficiency of rural song compared to urban song was significantly lower in the city. While differences between the two songs in woodland were generally minimal, some measures of the transmission efficiency of rural song were significantly lower than those of urban song, suggesting additional benefits to singing rural songs in this setting. In an attempt to create artificial urban song, we mimicked the increase in minimum frequency found several times previously in urban song. However, this did not replicate the same transmission properties as true urban song, suggesting changes in other song characteristics, such as temporal adjustments, are needed to further increase transmission of an avian signal in the city. We suggest that the structure of the acoustic environment, in addition to the background noise, plays an important role in signal adaptation.