A tubing assembly for entering multiple boreholes includes an outer shroud having an axial throughbore, and an inner tubular member disposed in the axial throughbore, wherein the tubular member is releasably coupled to the shroud, and wherein the outer diameter of the shroud is adjustable. A tubing assembly for entering multiple boreholes may also include a shroud having an axial throughbore, a movable tubular member disposed in the axial throughbore, and a releasable coupling between the shroud and the tubular member, wherein the releasable coupling includes a retracted position allowing entry of the tubing assembly into a junction between two boreholes, wherein the releasable coupling includes an expanded position allowing movement of the tubular member relative to the shroud and prevents re-entry of the tubing assembly into the junction.