A method of removing a drilling assembly from a wellbore, wherein the drilling assembly includes a transition region between a first section including a first cross-sectional area and a second section including a second cross-sectional area, wherein the first cross-sectional area is less than the second cross-sectional area, wherein the first section is farther from a terminal end of the drilling assembly than the second section, and further wherein the drilling assembly includes a fluid conduit configured to transmit a drilling fluid stream, the method comprising:
- withdrawing at least a portion of the drilling assembly from the wellbore;
- detecting a variable associated with packoff within the wellbore;
- and
- providing a fluidizing stream to a portion of a cuttings bed proximal the transition region, wherein the fluidizing stream includes a portion of the drilling fluid stream, and further wherein the providing includes selectively providing the fluidizing stream based at least in part on the variable associated with packoff.