This report discusses the advantages and challenges in using direct psychological personality profile and psychodynamic assessments (corresponding to Otto Kernberg’s model of personally organization) of suicide bombers and lone actors. Two studies that administered various psychological instruments (i.e., self-report inventories, semi-structured interviews, and projective tests) were used to assess these subjects in a prison setting, before or after their trial. Main findings showed that suicide bombers displayed low levels of ego strength with dependent and/or avoidant personality styles, while most of the lone actors presented evidence of psychiatric histories. Also, the main methodological advantages and challenges of the assessment procedures and instruments utilized are discussed. Self-report inventories were found to be less valid. In contrast, semi-structured interviews assisted in identifying a more comprehensive theoretical understanding of both personality dynamics and the discerning of traumatic experiences in participants’ background related primarily to their family history. Projective tests had limited and restricted responses i.e., lacked the necessary complexity. This pattern likely reflected those participants with either limited mental resources, maladaptive personality styles, or hostile responses toward their assessors. Future directions are discussed in a psycho-cultural theoretical perspective regarding the development risk/threat assessment instruments to discern potential perpetrators who are victims of trauma in families living under specific cultural contexts. We assume that these victims’ manifest dissociation defences, present tendencies to activate mobilization, and immobilization energetic systems. These systems evoke complex behaviour patterns triggering suicidal tendencies coupled with rage tendencies aiming to end the lives of others, in this context, perceived political enemies.