This narrative study examined the experiences of three pre-service teachers with different writing proficiency levels in conducting a cyclical self-assessment process in Academic Writing mediated by Scribo. The study interweaves three theories, namely the cyclical self-assessment process (Yan & Brown, 2017), reflection-on-action (Schön, 1987), and the writing process (Hyland, 2003). The data was obtained from the pre-service teachers’ reflective notes, artifacts, and semi-structured interviews. The present study revealed that three pre-service teachers with different writing proficiency levels showed that they engaged in the same stages proposed by Yan and Brown (2017), namely: (1) adopting formal criteria or internal goals; (2) seeking external feedback from Automated Written Corrective Feedback (AWCF) and internalizing the feedback; (3) self-reflection; (4) calibration process. Through their reflection-on-action, it was found that they faced some difficulties during the cyclical self-assessment process due to a lack of external feedback to reflect on the quality of their work, engage in revising process, and confirm their revision. Additionally, their level of trust in Scribo also plays a big role in engaging, effective cyclical self-assessment. The pre-service teacher with low trust in Scribo was likely to engage in an effective self-assessment process. Lastly, their metacognition was enhanced through the cyclical self-assessment process they had done which is proved by the strategy they plan to improve some stages of the cyclical self-assessment process in the future learning so that they could improve their writing result.