Error management training (EMT) encourages trainees to make errors by combining low structure training with error-encouraging prompts. The current study aimed to investigate whether self-regulation, which is the theoretical driver of EMT’s effectiveness, can be prompted without explicitly encouraging errors, retaining the benefits of EMT without the potentially harmful effects of error encouragement. A sample of 153 adults (18-70 years old, Mage = 41.80, SDage = 13.43, 62.7% female, 60.1% White) participated in an online Google Sheets training program in one of three experimental conditions. The conditions differed based on prompts that participants heard and read during practice: error management prompts, self-regulatory prompts (encouraging self-regulation without encouraging errors), or a control condition with no prompts. I hypothesized that EMT and self-regulatory prompts would lead to better post-training assessment performance than the control, and that the self-regulatory prompts would lead to better post-training assessment performance than the EMT prompts. I also hypothesized that age would interact with condition such that older trainees would either show worse performance due to the EMT prompts, which could be attributed to error encouragement, or from the presence of prompts in general, which could point to the distracting nature of prompts more broadly. No significant differences in post-training assessment performance by condition were found, nor did age interact with condition to impact post-training assessment performance. Therefore, the new theoretically-derived self-regulatory prompts were not more effective than EMT prompts, and perhaps more surprisingly, the broadly accepted benefit of EMT prompts over the control condition was not supported. This study contributes to the training literature by suggesting that error management training has important, unexplored boundary conditions to its effectiveness.