Index: AbstractGrailsMojo.java
===================================================================
--- AbstractGrailsMojo.java	(.../src/main/java/org/grails/maven/plugin/AbstractGrailsMojo.java)	(revision 3494)
+++ AbstractGrailsMojo.java	(.../trunk/src/main/java/org/grails/maven/plugin/AbstractGrailsMojo.java)	(revision 3507)
@@ -207,7 +207,25 @@
         try {
             classpath = new URL[deps.size() + 1];
             int index = 0;
-            for (Iterator iter = deps.iterator(); iter.hasNext();) {
+            
+            // See GRAILS-4969
+          	// patch markus.kramer@neofonie.de start
+            // make sure grails-bootstrap comes first
+          	Artifact[] sortedDeps = new Artifact[deps.size()];
+           	int i = 1;
+           	for (Iterator iter = deps.iterator(); iter.hasNext();) {
+           	    Artifact artifact = (Artifact) iter.next();
+           	    if ("org.grails".equals(artifact.getGroupId()) && "grails-bootstrap".equals(artifact.getArtifactId())) {
+           	        sortedDeps[0] = artifact;
+           	    } else {
+           	        sortedDeps[i] = artifact;
+           	        i++;
+          	    }
+           	}
+            
+        	for (Iterator iter = Arrays.asList(sortedDeps).iterator(); iter.hasNext();) {
+        		// patch markus.kramer@neofonie.de end
+        		// was: for (Iterator iter = deps.iterator(); iter.hasNext();) {
                 classpath[index++] = ((Artifact) iter.next()).getFile().toURI().toURL();
             }