This study examines the impact of a newly developed structured training on Singapore paramedics’ psychological comfort before the implementation of a prehospital termination of resuscitation (TOR) protocol. Following a before and after study design, the paramedics underwent a self-administered questionnaire to assess their psychological comfort level applying the TOR protocol, 22 months before and one month after a 3-h structured training session. The questionnaire addressed five domains: sociocultural attitudes on resuscitation and TOR, multi-tasking, feelings towards resuscitation and TOR, interactions with colleagues and bystanders and informing survivors. Overall psychological comfort total (PCT) scores and domain-specific scores were compared using the paired t-test with higher scores representing greater comfort. Ninety-six of the 345 eligible paramedics responded. There was no statistically significant change in the mean PCT scores at baseline and post-training; however, the “feelings towards resuscitation and TOR” domain improved by 4.77% (95% CI 1.42 to 8.13 and p = 0.006) and the multi-tasking domain worsened by 4.11% (95% CI −7.82 to −0.41 and p = 0.030). While the structured training did not impact on the overall psychological comfort levels, it led to improvements in the feelings of paramedics towards resuscitation and TOR. Challenges remain in improving paramedics’ psychological comfort levels towards TOR.