Crisis Information Management Systems (CIMS) have been used in Emergency and Disaster Response Management for decades. However, while these systems have emerged and improved over time, they still appear to provide lower efficacy when incidents become more complex, and, in particular, when used in the context of multijurisdictional responses to large and growing incidents and extreme events. Most CIMS like E Team, Veoci, or WebEOC are commercial off-the-shelf systems (COTS), which allow for and also require from emergency response units the customization of the application to their own specific needs. This survey-informed study took a look at practitioners’ experiences with one of the most widely used CIMS, that is, WebEOC. The results were mixed at best and confirm other studies, which pointed at WebEOC’s lack of scalability, interoperability, network security, and ease of use. The study concludes that in the face of ever more frequent incidents of greater magnitude the case for developing and deploying securely interoperable and scalable CIMS is compelling and has to be addressed.