Our goal is to provide empirical support for assumptions of the Doane, Kintsch, & Poison (1989; 1990) consuuciion integration model for generating complex commands in UNIX. In so doing we designed a methodology that may be used to examine the assumptions of other cognitive models. The planning task studied was the generation of complex sequences of UhfIX commands. The sequences were novel, and as such could not be recalled from memory. W e asked users whose VNIX experience varied to produce complex UNIX commands, and then provided help prompts when the commands they produced were erroneous. The help prompts were designed to assist the subjects with both knowledge and processes which our UNIX modeling efforts have suggested were lacking in less expert users. There are two major findings. First, it appears that experts respond to different prompts than do novices. Expert performance is helped by the presentation of abstract information, while novice and intermediate performance is modified by presentation of concrete information. Second, while presentation of specific prompts aids the less expert, it does not appear to be sufficient information to obtain optimal performance. To do this, the less expert subjects require information about the ordering of the items in a command. Our analyses suggest that information about the ordering of prompts helps the less expert with memory load problems in a manner coiuistent with skill acquisition theories.