Health information portals (HIP) are now common place. Governments and other health agencies are using HIPs extensively to reduce costs and distribute information more effectively. Generally, HIPs are not very technically sophisticated specifically in terms of options for improving searching. There are many ways in which searching and retrieving relevant information can be improved. This paper presents an exploratory study which investigated five HIPs. Each HIP offered a range of features and functionality to assist with searching. Our research explored the features and functionality of each HIP. Through usability evaluations we compared the response of users to each HIP and identified users’ preferences for improved searching. We found that HIPs with improved search functionality and other features that assisted searching were better received by the users. Users regarded these portals as easier to understand, easier to use, required fewer steps in retrieving information and were more likely to say they would return. Comments from users are provided to illustrate further the importance of providing effective functionality. The paper concludes with recommendations for Health Information Portal builders on what is needed to improve the user search experience.