Thanks to an email from Martin, I had a strong indicator of where to look. I 
checked out tomcat 8 from trunk and  validated in eclipse in debug mode. (FYI is broken due to missing commons pool, had to tweak a 

From snippet below (line 737), jars[] does not only 
contain jars, but also any other resources. i added a howTo.txt file in 
WEB-INF/lib, which results in  jars.length will NEVER equal 

Fix is simple - just filter out the non-jar, non-executable elements b4 
comparing. Workaround is equally trivial - remove said elements from the the 
lib folder.
Hope this helps,

        // Check if JARs have been added or removed
        WebResource[] jars = resources.listResources("/WEB-INF/lib");

        if (jars.length > jarModificationTimes.size()) {
            return true;
        } else if (jars.length < jarModificationTimes.size()){
            return true;

        for (WebResource jar : jars) {
            if (jar.getName().endsWith(".jar") && jar.isFile() && 
jar.canRead()) {

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