After the national introduction of the ePrescription in Belgium to the broader public in 2014, community pharmacists are still not satisfied completely. Reasons are (1) low acceptance of the implementation due to slow systems, (2) high reported downtimes, and (3) alert fatigue due to technical and incomprehensible error messages. Therefore, we investigated which technical errors occur in the flow of handling an ePrescription and how these errors can be avoided. A cross-sectional design was used to capture interactions of all national community pharmacists connected to the national eHealth platform on a randomly chosen working day. Per interaction, the number of errors made was observed. In total, 567,883 interactions were registered and analyzed, of which the getPrescription interaction, to download the ePrescription from the national server, was most prevalent (n = 196,433; 37.21%). A difference of 14,961 interaction calls was observed without reaching a final state (delivered or undelivered). Reasons for these differences are repetitive calls for obtaining the ePrescription or by trying to obtain the prescription again when this should no longer be possible (e.g., when an ePrescription is already delivered or archived). When looking at the markAsDelivered, markAsUndelivered or markAsArchived interactions, most of the technical handling errors are due to attempts that generate not allowed state transitions. Most of these incorrect state transitions could have been avoided by maintaining the state diagram in the pharmacist's system to enforce legal transitions and by training the community pharmacists to handle ePrescriptions appropriately.