It is clear from the case law of Croatian courts that intentional disadvantaging the creditors (regulated in Article 202 of the Insolvency Act) is the most commonly used ground for contesting the legal transactions of an insolvent debtor. On this ground, all legal transactions undertaken in the suspect period of as long as ten years before the submission of the application for opening (pre-)insolvency proceedings until the opening insolvency proceedings can be contested. The authorized contester, however, in litigation has a tall order of proving not only that the debtor took action with the intent to disadvantage its creditors but also that the opponent of the contestation was aware of that intent. The debtor’s intent to disadvantage its creditors and the awareness of the opponent of the contestation are both determined on the basis of objective indications that are at the heart of the analysis of this paper. Incongruent settlement, the unequal value of consideration, unusual contractual clauses, the proximity of the insolvency debtor and the opponent of the contestation, and the debtor’s (threatening) inability to pay his debts are most often recognized in case law as indications of intentional disadvantaging the creditors of an insolvent debtor. In addition to certain objections to the normative regulation of the institute itself, especially regarding the drafting of presumptions that make it easier to prove the contester’s awareness of the debtor’s intention to disadvantage its creditors, the paper presents a critical assessment of case law that could facilitate its harmonization and serve as a guide to authorized contesters as to whether it is appropriate to engage in contestation or not.