In this study we investigate whether speakers, in line with the predictions of the Hyper- and Hypospeech theory, speed up most during the least informative parts and less during the more informative parts, when they are asked to speak faster. We expected listeners to benefit from these changes in timing, and our main goal was to find out whether making the temporal organisation of artificially time-compressed speech more like that of natural fast speech would improve intelligibility over linear time compression. Our production study showed that speakers reduce unstressed syllables more than stressed syllables, thereby making the prosodic pattern more pronounced. We extrapolated fast speech timing to even faster rates because we expected that the more salient prosodic pattern could be exploited in difficult listening situations. However, at very fast speech rates, applying fast speech timing worsens intelligibility. We argue that the non-uniform way of speeding up may not be due to an underlying communicative principle, but may result from speakers’ inability to speed up otherwise. As both prosodic and segmental information contribute to word recognition, we conclude that extrapolating fast speech timing to extremely fast rates distorts this balance between prosodic and segmental information.