In this article, through comparing two highly skilled migrant groups in London, we explore how new types of information and communication technologies (ICTs) shape the form and content of transnational practices through time and space. In so doing, we aim to contribute to several debates in the field of migration studies. First, our findings highlight enduring practical constraints emanating from everyday routines and responsibilities, thus questioning the extent to which ICTs may be shrinking the globe and freeing people, even highly skilled ones, from spatial and temporal fixity. Second, we challenge assumptions about the ease of transnationalism by exploring the range and complexity of long‐distance interpersonal relationships and their dynamics over time. Third, by focusing on a comparison of relatively affluent, highly skilled migrants, we question the usefulness of the category of ‘middling migrants’. Our findings illustrate that, within this general and wide ranging category, there are diverse experiences, expectations and opportunities of maintaining contact with friends and family at home.