Monarch butterflies (Danus plexippus) are well known for extraordinarily long-distance annual migrations between over-wintering grounds in Mexico and summer breeding in North America. Within the last 20 years, eastern populations of the monarch butterfly have declined by more than 80 percent, and more than a 99 percent decline in the western populations in North America. The regulatory requirements associated with the potential federal listing of the butterfly for protection under the Endangered Species Act (ESA) would lead to extensive and costly delays of VDOT general operation activities such as maintaining vegetated rights-of-way (ROW) and modernization construction activities of critical infrastructure. The University of Illinois Chicago (UIC) Rights-of-Way Habitat Working Group developed an integrated Programmatic Candidate Conservation Agreement with Assurances (CCAA) for the monarch, which is a formal, voluntary conservation agreement between the U.S. Fish and Wildlife Service (USFWS) and one or more non-federal property owner(s) in the energy and transportation sectors nationwide, with the goal to enroll up to 26 million acres of energy and transportation lands, and establish about 2.3 million acres of monarch foraging and breeding habitat in North America. In 2020, VDOT joined this effort to reestablish suitable monarch habitat by promoting conservation measures that reduce or remove key threats through proactive vegetation management practices. Many of VDOT’s roadside practices and integrated vegetation management plans are currently benefiting monarchs and pollinator habitat in general, mainly through reduced mowing (one cut/year in dormant season), or targeted herbicide spraying to remove noxious or invasive plant species. VDOT will also receive assurances from the USFWS that additional conservations measures beyond those in the CCAA will not be required and additional restrictions on covered activities will not be imposed. These factors were key buy-in talking-points for management’s decision to join as a CCAA partner. Several challenges were met during the decision making process, such as defining what ROW lands to enroll, where implementation and monitoring of conservation measures on adopted acres would be most beneficial for the monarch, and the general unavailability of GIS mapping of VDOT’s road system ROWs and roadside features. Due to considerable variation in vegetation management needs across the state, VDOT Maintenance and Environmental formed an internal District Joint Working Group to collaborate and address specific needs for the Monarch CCAA. Through this effort, VDOT updated the Maintenance Best Practices for mowing by incorporating avoidance and minimization measures to benefit the monarch and pollinators. VDOT also contracted to obtain LiDAR mapping of the entire interstate system that provided crucial details on roadside features that will be used for internal program asset tracking for intra-agency divisions, programs and operations. Enrolling in the CCAA has prompted VDOT to re-evaluate roadside maintenance and operations to ensure encumbered lands are meeting full potential and regulatory requirements.