See the following minimal example (I'm not trying to typeset urls or filesystem paths in this way, just regular text): %%%%%%%%%%%%%%%%%%%%%%%%%%%% \def\myslash{/\penalty-5000} \starttext \type{/} {\bfd Love/Hate/Play/Love/Hate/Play/Love/Hate/Play/Love/Hate/Play} \type{\slash} {\bfd Love\slash Hate\slash Play\slash Love\slash Hate\slash Play\slash Love\slash Hate\slash Play\slash Love\slash Hate\slash Play} \type{\textslash} {\bfd Love\textslash Hate\textslash Play\textslash Love\textslash Hate\textslash Play\textslash Love\textslash Hate\textslash Play\textslash Love\textslash Hate\textslash Play} \type{\myslash} {\bfd Love\myslash Hate\myslash Play\myslash Love\myslash Hate\myslash Play\myslash Love\myslash Hate\myslash Play\myslash Love\myslash Hate\myslash Play} \stoptext %%%%%%%%%%%%%%%%%%%%%%%%%%%% Neither one of the first three solutions above give me the right thing, because the line won't break at /. What am I missing? A workaround seems to be \def\myslash{/\penalty-5000} and then using \myslash instead of \slash, but I'm pretty sure I'm not doing this right. Thanks in advance -- Marco