This paper hopes to enhance understanding about entrenched grievance in a couple of ways: (a) Initially, the paper reviews how entrenched grievance reflects melancholic states of mind in terms of its avoidance of the pain of loss and change. But the main contribution of the paper is likely to be found in (b), that is, via detailed clinical material, the paper illustrates how earnest efforts on the part of the analyst to bring understanding may lead to cognitive entrapments such as the convictions incumbent in the “knowing” analyst. Further, that this knowing analyst may need to become aggrieved, that is, narrow, impatient and concrete towards her patient’s entrenchment, and then to recogize this plight in herself before she can genuinely hear her patient’s grievance about her from a wider view, that is as a complaint from the “lively self”, deserving recognition. The clinical detail demonstrates that such recognition softened the patient’s grievance, allowing both members of the dyad to become more collaborative and open to the pains and growth available from mourning states of mind.