Cooperation across national borders is of paramount importance for the security in border close regions. Timely and adequate training, reflection, and preparation are core tools for facilitating and stimulating such interregional cooperation. Hence, NetAgora, a service oriented web portal for security cooperation, was designed. In NetAgora there is first a service package with accident- and emergency scenarios. Here multi-actors can train their cooperation and decision making skills. The R-statistics open source package is applied for recording and analyzing data from those training occasions. In subsequent debriefing sessions this is used for post-learning. Further, from anticipatory modeling and simulation it is found that rescue operations are delayed and misguided due to shortcomings in the communication between security command and communication centers. Hence, the NetAgora Learning System is designed and prototyped in order to overcome that problem. It will facilitate and stimulate reflection in action and double loop learning and aims at improving communication patterns by anticipatory pre-learning.