This paper describes the challenges of introducing a digital tool to trainee teachers. A group of nineteen undergraduate students studying primary education and in their third year of a four year course was introduced to PebblePad5. PebblePad is an online tool which is not new in the world of ITE. However, the latest version has more useful features and is less ‘clunky’ than older versions. The students each had their own private account where eventually they would be expected to store all of their placement files, add multi-modal content and then choose to share some or all of this content publically or by personal invitation via email. One of the benefits for us as an ITE provider is that we can view our students’ files electronically and comment on them without necessarily making the one/two hour round trip to the placement school. Although students used some technology, this research shows that students need more training in using technology competently in the workplace setting. Phase One of the project was to encourage the students to write their reflections on placement digitally. It was hoped that the students would be enthusiastic about using PebblePad and I would see an improvement in the levels of engagement with the reflective process and thus, the quality of teaching and learning as a result of this. Data obtained from questionnaires and a focus group indicate that PebblePad was viewed as a useful tool, but training issues and time constraints of the project meant it was not as successful for this cohort as was hoped. This paper discusses the issues that arose and the plan to overcome these barriers in the next phase of the implementation of PebblePad.