Although the principle of legitimate expectations appeared in earlier drafts of the newest Serbian law on general administrative procedure, it was eventually downplayed to the level of guaranteeing predictability in administrative practice. The inclusion of the new principle was justified by harmonization of Serbian legislation with the principles of a common European Administrative Space. The contribution explores the notion of legitimate expectations in comparative law – ranging from so-called procedural to substantive expectations, with the possibility of contra legem effect of the principle. European administrative law scholars have long ago posed questions relating to the tension between the law and legal certainty and satisfying individual parties’ (legitimate) expectations. Parties to administrative proceedings should, in line with the request for legal certainty, be aware of what type of action they can expect from the administration. On the other hand, life often necessitates changes in legislation and, even on occasions before that, adaptations to administrative behaviour. In comparative analysis, particular attention shall be paid to legislation and caselaw of the former Yugoslav states, since they share a history of common administrative legislation. The author aims to situate the Serbian version of this legal institute within the given range and, with an optimistic view to existent caselaw of the Constitutional Court, to point towards possibilities for its future implementation in the caselaw of the Administrative Court and in administrative practice.