Expectation-related bias may configure individuals’ perception of their surrounding environment and of the elements present in it. This study aimed to determine the repercussions of environmental (weather elements) or subject-inherent factors (sex, age, or personality features) on judgment bias. A cognitive bias test was performed in eight Miniature jennies and four jacks. Test comprised habituation, training and testing phases during which subjects were trained on how to complete the test and scored based on their latency to approach an ambiguous stimulus. A questionnaire evaluating eleven personality features was parallelly completed by three caretakers, five operators and two care assistants to determine the links between personality features and judgment bias. Adjusted latencies did not significantly differ between sexes (Mann–Whitney test, p > 0.05). Although Miniature donkeys can discriminate positive/negative stimuli, inter-individual variability evidences were found. Such discrimination is evidenced by significant latency differences to approach positive/negative stimuli (33.7 ± 43.1 vs. 145.5 ± 53.1 s) (Mann–Whitney test, p < 0.05). Latencies significantly increased with patience, indicative of an expression of pessimism. Better understanding judgement bias mechanisms and implications may help optimize routine handling practices in the framework of animal welfare.