In 1994, Jonathan Grudin wrote his famous paper Eight Challenges for Groupware Developers; The question is whether these challenges still persist, or have we moved on here 30 years later? We revisit the challenges empirically through ethnographic observations in two companies examining their work practices, organizational structure, and cooperative setups concerning their use of groupware technologies. Today, groupware is seamlessly integrated into organizations, considered essential infrastructure that becomes part of the daily work routine. Contextualizing the original challenges proposed by Grudin, we categorize them into cooperative challenges, social challenges, and organizational challenges, and refine their phrasings to reflect present and future considerations faced by developers of groupware technologies. While the main arguments of the social and organizational challenges remain consistent, we rephrase the cooperative challenges as emergent exception handling and exaggerated accessibility to reflect the emerging characteristics associated with the ubiquity and seamless integration of groupware.