diff --git a/src/main/java/org/rundeck/client/Rundeck.java b/src/main/java/org/rundeck/client/Rundeck.java
index b1f6878a..de67c7ef 100644
--- a/src/main/java/org/rundeck/client/Rundeck.java
+++ b/src/main/java/org/rundeck/client/Rundeck.java
@@ -1,12 +1,11 @@
 package org.rundeck.client;
 
-import okhttp3.*;
+import okhttp3.HttpUrl;
+import okhttp3.JavaNetCookieJar;
+import okhttp3.OkHttpClient;
 import okhttp3.logging.HttpLoggingInterceptor;
 import org.rundeck.client.api.RundeckApi;
-import org.rundeck.client.util.FormAuthInterceptor;
-import org.rundeck.client.util.Client;
-import org.rundeck.client.util.QualifiedTypeConverterFactory;
-import org.rundeck.client.util.StaticHeaderInterceptor;
+import org.rundeck.client.util.*;
 import retrofit2.Retrofit;
 import retrofit2.converter.jackson.JacksonConverterFactory;
 import retrofit2.converter.simplexml.SimpleXmlConverterFactory;
@@ -78,11 +77,21 @@ public static Client<RundeckApi> client(
             final int httpLogging
     )
     {
+        String appBaseUrl = buildBaseAppUrlForVersion(baseUrl);
         String base = buildApiUrlForVersion(baseUrl, apiVers);
 
         OkHttpClient.Builder callFactory = new OkHttpClient.Builder()
                 .addInterceptor(new StaticHeaderInterceptor("X-Rundeck-Auth-Token", authToken));
 
+        String bypassUrl = System.getProperty("rundeck.client.bypass.url", System.getenv("RUNDECK_BYPASS_URL"));
+
+        if (null != bypassUrl) {
+            //fix redirects to external Rundeck URL by rewriting as to the baseurl
+            callFactory.addNetworkInterceptor(new RedirectBypassInterceptor(
+                    appBaseUrl,
+                    bypassUrl
+            ));
+        }
         if (httpLogging > 0) {
             HttpLoggingInterceptor logging = new HttpLoggingInterceptor();
 
@@ -158,7 +167,15 @@ public static Client<RundeckApi> client(
                 )
 
         ));
-
+        String bypassUrl = System.getProperty("rundeck.client.bypass.url", System.getenv("RUNDECK_BYPASS_URL"));
+
+        if (null != bypassUrl) {
+            //fix redirects to external Rundeck URL by rewriting as to the baseurl
+            callFactory.addNetworkInterceptor(new RedirectBypassInterceptor(
+                    appBaseUrl,
+                    normalizeUrlPath(bypassUrl)
+            ));
+        }
         if (httpLogging > 0) {
             HttpLoggingInterceptor logging = new HttpLoggingInterceptor();
 
@@ -190,8 +207,13 @@ public static Client<RundeckApi> client(
      */
     private static String buildApiUrlForVersion(String baseUrl, final int apiVers) {
         if (!baseUrl.matches("^.*/api/\\d+/?$")) {
-            return baseUrl + "/api/" + (apiVers) + "/";
-        } else if (!baseUrl.matches(".*/$")) {
+            return normalizeUrlPath(baseUrl) + "api/" + (apiVers) + "/";
+        }
+        return normalizeUrlPath(baseUrl);
+    }
+
+    private static String normalizeUrlPath(String baseUrl) {
+        if (!baseUrl.matches(".*/$")) {
             return baseUrl + "/";
         }
         return baseUrl;
@@ -205,10 +227,8 @@ private static String buildApiUrlForVersion(String baseUrl, final int apiVers) {
     private static String buildBaseAppUrlForVersion(String baseUrl) {
         Matcher matcher = API_VERS_PATTERN.matcher(baseUrl);
         if (matcher.matches()) {
-            return matcher.group(1);
-        } else if (!baseUrl.matches(".*/$")) {
-            return baseUrl + "/";
+            return normalizeUrlPath(matcher.group(1));
         }
-        return baseUrl;
+        return normalizeUrlPath(baseUrl);
     }
 }
diff --git a/src/main/java/org/rundeck/client/util/RedirectBypassInterceptor.java b/src/main/java/org/rundeck/client/util/RedirectBypassInterceptor.java
new file mode 100644
index 00000000..86b16659
--- /dev/null
+++ b/src/main/java/org/rundeck/client/util/RedirectBypassInterceptor.java
@@ -0,0 +1,50 @@
+package org.rundeck.client.util;
+
+import okhttp3.Interceptor;
+import okhttp3.Response;
+
+import java.io.IOException;
+
+/**
+ * Change redirect behavior, if Location begins with the bypass url, replace that part with the app URL.
+ */
+public class RedirectBypassInterceptor implements Interceptor {
+    private String appBaseUrl;
+    private String bypassUrl;
+
+    public RedirectBypassInterceptor(final String appBaseUrl, final String bypassUrl) {
+        this.appBaseUrl = appBaseUrl;
+        this.bypassUrl = bypassUrl;
+    }
+
+    @Override
+    public Response intercept(final Chain chain) throws IOException {
+        Response originalResponse = chain.proceed(chain.request());
+        if (originalResponse.isRedirect()) {
+            String originalLocation = originalResponse.header("location");
+            String newUrl = remapUrl(originalLocation, bypassUrl, appBaseUrl);
+            if (null != newUrl) {
+                return originalResponse.newBuilder()
+                                       .header("Location", newUrl)
+                                       .build();
+            }
+        }
+        return originalResponse;
+    }
+
+    /**
+     * Replace the prefix of the originurl that starts with the bypassurl string with the appbaseurl string
+     *
+     * @param origUrl
+     * @param bypassUrl
+     * @param appBaseUrl
+     *
+     * @return
+     */
+    public static String remapUrl(final String origUrl, final String bypassUrl, final String appBaseUrl) {
+        if (origUrl.startsWith(bypassUrl)) {
+            return appBaseUrl + origUrl.substring(bypassUrl.length());
+        }
+        return null;
+    }
+}
diff --git a/src/test/groovy/org/rundeck/client/util/RedirectBypassInterceptorSpec.groovy b/src/test/groovy/org/rundeck/client/util/RedirectBypassInterceptorSpec.groovy
new file mode 100644
index 00000000..ce1a3bed
--- /dev/null
+++ b/src/test/groovy/org/rundeck/client/util/RedirectBypassInterceptorSpec.groovy
@@ -0,0 +1,23 @@
+package org.rundeck.client.util
+
+import spock.lang.Specification
+
+/**
+ * Created by greg on 9/9/16.
+ */
+class RedirectBypassInterceptorSpec extends Specification {
+    def "remap"() {
+        when:
+        String result = RedirectBypassInterceptor.remapUrl(orig, bypass, app)
+
+
+        then:
+        result == expect
+
+        where:
+        orig                    | bypass            | app               | expect
+        "http://host1/c1/path1" | "http://host1"    | "http://host2/c2" | "http://host2/c2/c1/path1"
+        "http://host1/c1/path1" | "http://host1/c1" | "http://host2/c2" | "http://host2/c2/path1"
+        "http://host1/c1/path1" | "http://host1/c1" | "http://host2"    | "http://host2/path1"
+    }
+}