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Treatment goals in psychoanalysis often include changes in underlying psychological structures. Different patterns of change have been demonstrated in anaclitic and introjective patients. In a series of 14 cases, we took a further step and examined changes in the anaclitic–introjective personality configurations following psychoanalysis, as well as patients' experiences of these changes. Clinical case formulations were based on repeated interviews and the application of prototype-matching methodology. Patients' experiences were explored by applying inductive thematic analysis. We found a development toward more mature levels of differentiation and individuation in the anaclitic group, whereas relatedness and intimacy remained problematic in some introjective cases. Patients described their experienced changes in terms of complementary personality configuration, but the introjective group described more benefits from psychoanalysis. Several patients expressed their ambivalence toward these changes and a feeling of loss of their former selves. Patients' view of their analysts and the analytic method were congruent with patients' primary personality configuration. To reactivate developmental processes, the psychoanalytic technique has to be adjusted to the anaclitic and introjective patients' different needs and defenses.