An infrastructure is provided for gathering diagnostic data that is relevant to an error or other conditions detected in a monitored system. A diagnosability framework is provided that automates the gathering of relevant diagnostic data upon occurrence of the condition in the monitored system. In one embodiment, context data is determined for the condition detected in the monitored system. A rule-based engine is provided that is configured to automatically determine one or more actions to be performed for the condition detected in the monitored system based on the determined context data. The actions may include performing tasks that gather diagnostic data that is relevant to the detected condition, store the gathered diagnostic data in a repository, recommend one or more diagnostic actions to a user, and other diagnostic related actions.