Several explanations could apply crossing psychology and linguistics:
Cognitive: It is perhaps bold to suggest that there could be a perfectly constructed error message. Reading comprehension and interpretation is impacted by a diverse array of cognitive processes, including literal, inferential and evaluative cognitive processes(Basaraba et al., 2013). Despite having comprehensive vocabulary and general knowledge, individuals may still encounter difficulties with text comprehension due to metacognitive deficits with memory and reading strategies(Oakhill et al., 2015), diversity of cultural background(Yousef et al., 2014), and developmental opportunity(Paris & Hamilton, 2009). Given the extensive array of cognitive processes required to comprehend text, it is not surprising that a range of interpretations will exist, no matter how well constructed the response is.
Opportunity cost: The amount of time an individual will devote to solving the conundrum of the error message is dependent on their other priorities(Kurzban et al., 2013). The individual is unlikely to know in advance how much time it will take to comply with the error message, so they are likely to make assumptions. If the opportunity cost associated with the estimated time is less than the value the individual estimates is associated with other opportunities, then they are unlikely to respond in the manner expected.
Learned behaviours will also be involved. If the user has learned from prior interactions that the same result can be achieved through non-compliance, then they are likely to repeat this learned behavior in the future.
In addition to the above, self-efficacy(Bandura & Locke, 2003) and embarrassment avoidance(Jiang et al., 2018) may have a role to play.
Bandura, A., & Locke, E. A. (2003). Negative self-efficacy and goal effects revisited [Review of Negative self-efficacy and goal effects revisited]. The Journal of Applied Psychology, 88(1), 87–99. psycnet.apa.org. https://doi.org/10.1037/0021-9010.88.1.87
Basaraba, D., Yovanoff, P., Alonzo, J., & Tindal, G. (2013). Examining the structure of reading comprehension: do literal, inferential, and evaluative comprehension truly exist? Reading and Writing, 26(3), 349–379. https://doi.org/10.1007/s11145-012-9372-9
Jiang, L., Drolet, A., & Scott, C. A. (2018). Countering embarrassment-avoidance by taking an observer’s perspective. Motivation and Emotion, 42(5), 748–762. https://doi.org/10.1007/s11031-018-9673-7
Kurzban, R., Duckworth, A., Kable, J. W., & Myers, J. (2013). An opportunity cost model of subjective effort and task performance. The Behavioral and Brain Sciences, 36(6), 661–679. https://doi.org/10.1017/S0140525X12003196
Oakhill, J. V., Berenhaus, M. S., & Cain, K. (2015). Children’s reading comprehension and comprehension difficulties. In A. Pollatsek & R. Treiman (Eds.), The Oxford Handbook of Reading (pp. 344–360). Oxford.
Paris, S. G., & Hamilton, E. E. (2009). The Development of Children’s Reading Comprehension. In S. E. Israel & G. G. Duffy (Eds.), Handbook of Research on Reading Comprehension (pp. 32–53). Routledge.
Yousef, H., Karimi, L., & Janfeshan, K. (2014). The Relationship between Cultural Background and Reading Comprehension. Theory and Practice in Language Studies, 4(4). https://doi.org/10.4304/tpls.4.4.707-714