diff --git a/components/webapp-authenticator-framework/org.wso2.carbon.webapp.authenticator.framework/src/main/java/org/wso2/carbon/webapp/authenticator/framework/WebappAuthenticationValve.java b/components/webapp-authenticator-framework/org.wso2.carbon.webapp.authenticator.framework/src/main/java/org/wso2/carbon/webapp/authenticator/framework/WebappAuthenticationValve.java
index c1cf0897dc2..8c837c53380 100644
--- a/components/webapp-authenticator-framework/org.wso2.carbon.webapp.authenticator.framework/src/main/java/org/wso2/carbon/webapp/authenticator/framework/WebappAuthenticationValve.java
+++ b/components/webapp-authenticator-framework/org.wso2.carbon.webapp.authenticator.framework/src/main/java/org/wso2/carbon/webapp/authenticator/framework/WebappAuthenticationValve.java
@@ -106,6 +106,14 @@ public class WebappAuthenticationValve extends CarbonTomcatValve {
     }
 
     private boolean isNonSecuredEndPoint(Request request) {
+        if (request.getCoyoteRequest() != null && request.getCoyoteRequest().getMimeHeaders() !=
+                null && request.getCoyoteRequest().getMimeHeaders().getValue(Constants
+                .HTTPHeaders.HEADER_HTTP_AUTHORIZATION) != null) {
+            //This is to handle the DEP behaviours of the same endpoint being non-secured in the
+            // first call and then being secured in the second call which comes with the basic
+            // auth header.
+            return false;
+        }
         String uri = request.getRequestURI();
         if (uri == null) {
             uri = "";
@@ -146,8 +154,9 @@ public class WebappAuthenticationValve extends CarbonTomcatValve {
             String msg = "Failed to authorize incoming request";
             if (authenticationInfo.getMessage() != null && !authenticationInfo.getMessage().isEmpty()) {
                 msg = authenticationInfo.getMessage();
-                response.setHeader("WWW-Authenticate", msg);
+                response.setHeader("WWW-Authenticate", "Basic");
             }
+
             if (log.isDebugEnabled()) {
                 log.debug(msg + " , API : " + Encode.forUriComponent(request.getRequestURI()));
             }
diff --git a/components/webapp-authenticator-framework/org.wso2.carbon.webapp.authenticator.framework/src/main/java/org/wso2/carbon/webapp/authenticator/framework/authenticator/BasicAuthAuthenticator.java b/components/webapp-authenticator-framework/org.wso2.carbon.webapp.authenticator.framework/src/main/java/org/wso2/carbon/webapp/authenticator/framework/authenticator/BasicAuthAuthenticator.java
index 1b2afedc460..b0e49a7bd3c 100644
--- a/components/webapp-authenticator-framework/org.wso2.carbon.webapp.authenticator.framework/src/main/java/org/wso2/carbon/webapp/authenticator/framework/authenticator/BasicAuthAuthenticator.java
+++ b/components/webapp-authenticator-framework/org.wso2.carbon.webapp.authenticator.framework/src/main/java/org/wso2/carbon/webapp/authenticator/framework/authenticator/BasicAuthAuthenticator.java
@@ -50,9 +50,6 @@ public class BasicAuthAuthenticator implements WebappAuthenticator {
 
     @Override
     public boolean canHandle(Request request) {
-        if (!isAuthenticationSupported(request)) {
-            return false;
-        }
         if (request.getCoyoteRequest() == null || request.getCoyoteRequest().getMimeHeaders() == null) {
             return false;
         }
@@ -84,6 +81,7 @@ public class BasicAuthAuthenticator implements WebappAuthenticator {
                 authenticationInfo.setTenantDomain(Utils.getTenantDomain(tenantId));
                 authenticationInfo.setTenantId(tenantId);
             } else {
+                authenticationInfo.setMessage("Failed to authorize incoming request.");
                 authenticationInfo.setStatus(Status.FAILURE);
             }
         } catch (UserStoreException e) {