The lack of digital infrastructure in rural communities hinders the capacity to adopt flexible workplace practices such as telecommuting and teleworking. Individuals and businesses that reside in underserved communities in rural Ontario are left behind in today’s digital age due to the inability to meet minimum bandwidth speeds (50/10 Mbps), as prescribed by the Canadian Radio-Television and Telecommunications Commission (CRTC). While the Greater Toronto Hamilton Area (GTHA) remains unaffordable, the solution of urban sprawl in peri-urban and rural areas fosters various economic benefits, such as the investment of broadband internet. This research will examine the socio-economic impacts of rural broadband, specifically telecommuting and teleworking, through a regional planning lens. Results from this research will support the recommendation and development of telecommuting and teleworking policy frameworks within municipal Official Plans and private organizations. Thus, current broadband deployment initiatives must accommodate the rural telecommuter and further bridge the urban-rural digital divide.