Trying to find a better way of finding something rather then looping through list from top to bottom.
Can your context rules be precomputed into any sort of hierarchical match tree once at application initialization?

HashMap&lt;String, HashMap&lt;String, List&lt;ContextRule&gt;&gt;&gt; contextRuleMap

public boolean match (Context context, Map&lt;String, Map&lt;String, List&lt;ContextRule&gt;&gt; contextRuleMap)
{
    Map&lt;String, List&lt;ContextRule&gt;&gt; rulesByApplication = contextRuleMap[context.getUser()];

    for (ContextRule contextRule : rulesByApplication[context.getApplication()]) {
         // Existing logic for remaining 'match' of service and operation
    }

    return false;
}


You can pre-compute your 'match tree' to as many 'levels deep' as you need to by User -> Application -> Service -> Operation to achieve the necessary performance.