--- a/web.project/src/org/netbeans/modules/web/project/resources/build-impl.xsl	
+++ a/web.project/src/org/netbeans/modules/web/project/resources/build-impl.xsl	
@@ -1347,7 +1347,7 @@ 
             
             <target name="debug">
                 <xsl:attribute name="description">Debug project in IDE.</xsl:attribute>
-                <xsl:attribute name ="depends">init,compile,compile-jsps,-do-compile-single-jsp,-pre-dist,-do-tmp-dist-with-manifest,-do-tmp-dist-without-manifest</xsl:attribute>
+                <xsl:attribute name ="depends">init,compile,compile-jsps,-do-compile-single-jsp,-pre-dist,-do-tmp-dist-with-manifest,-do-tmp-dist-without-manifest,-init-cos</xsl:attribute>
                 <xsl:attribute name="if">netbeans.home</xsl:attribute>
                 <nbstartserver debugmode="true"/>
                 <antcall target="connect-debugger"/>
@@ -1357,7 +1357,18 @@ 
             </target>
             
             <target name="connect-debugger" if="do.debug.server" unless="is.debugged">
-                <nbjpdaconnect name="${{name}}" host="${{jpda.host}}" address="${{jpda.address}}" transport="${{jpda.transport}}">
+                <condition>
+                    <xsl:attribute name="property">dos.listening.cp</xsl:attribute>
+                    <xsl:attribute name="value">
+                        <xsl:choose>
+                            <xsl:when test="/p:project/p:configuration/webproject3:data/webproject3:web-services/webproject3:web-service|/p:project/p:configuration/webproject3:data/webproject3:web-service-clients/webproject3:web-service-client">${{debug.classpath}}:${{j2ee.platform.classpath}}:${{ws.debug.classpaths}}</xsl:when>
+                            <xsl:otherwise>${debug.classpath}:${j2ee.platform.classpath}</xsl:otherwise>
+                        </xsl:choose>
+                    </xsl:attribute>
+                    <xsl:attribute name="else"/>
+                    <istrue value="${{deploy.on.save}}" />
+                </condition>
+                <nbjpdaconnect name="${{name}}" host="${{jpda.host}}" address="${{jpda.address}}" transport="${{jpda.transport}}" listeningcp="${{dos.listening.cp}}">
                     <xsl:choose>
                         <xsl:when test="/p:project/p:configuration/webproject3:data/webproject3:web-services/webproject3:web-service|/p:project/p:configuration/webproject3:data/webproject3:web-service-clients/webproject3:web-service-client">
                             <classpath>