A wellbore tractor is capable of being positioned in a wellbore that includes a cased section, a first uncased section downhole of the cased section, and a second uncased section downhole of the first uncased section. The wellbore tractor is capable of self-propelling itself through the wellbore. An anchoring system is connected to the wellbore tractor. The anchoring system includes an appendage. When the wellbore tractor is in the cased section, the anchoring system is capable of extending the appendage from the cased section through the first uncased section into the second uncased section, anchoring the appendage in the second uncased section, and guiding the wellbore tractor from the cased section past the first uncased section and into the second uncased section.