Access obstruction in conflict settings has emerged as a critical operational and policy concern across the humanitarian sector, but there remains a dearth of analysis regarding the ways in which humanitarian organizations perpetuate self-inflicted access obstacles. Drawing on qualitative interviews conducted with local and international actors negotiating frontline humanitarian access in Somalia, this paper will examine the ways in which this context elucidates this phenomenon. Toward this end, this paper examines two dimensions of humanitarian access obstruction in this context. The first set of dynamics consists of externally imposed obstacles that stem from governmental actors, Al-Shabaab, access "gatekeepers" motivated by financial gain, and the insecure nature of the environment. The second set of dynamics consists of self-inflicted dimensions of access obstruction that emanate from decisions that international humanitarian organizations (IHOs) have made at the strategic or policy level. These issues include the physical "bunkerization" of IHOs, programmatic shortcomings, the discounting of local humanitarian actors' agency, and the ways that IHOs exhibit programmatic partiality in response to donors' interests and counterterrorism legislation. Through examining these issues, this paper highlights fact that, although the discourse on humanitarian access obstruction tends to emphasize difficulties arising from externally imposed obstacles, it is also important to interrogate the value and methods of humanitarian programming itself.