diff --git a/mangooio-core/src/main/java/io/mangoo/configuration/Config.java b/mangooio-core/src/main/java/io/mangoo/configuration/Config.java
index 99dcbcdf3b..af99023520 100644
--- a/mangooio-core/src/main/java/io/mangoo/configuration/Config.java
+++ b/mangooio-core/src/main/java/io/mangoo/configuration/Config.java
@@ -4,6 +4,8 @@
 import java.io.FileInputStream;
 import java.io.IOException;
 import java.io.InputStream;
+import java.util.ArrayList;
+import java.util.List;
 import java.util.Map;
 import java.util.Map.Entry;
 import java.util.Objects;
@@ -130,25 +132,27 @@ private void load(String parentKey, Map<String, Object> map) {
      * Decrypts all encrypted config value
      */
     private void decrypt() {
-        String key = null;
         Crypto crypto = new Crypto(this);
 
         for (final Entry<String, String> entry : this.values.entrySet()) {
             if (isEncrypted(entry.getValue())) {
-                if (StringUtils.isBlank(key)) {
-                    key = getMasterKey();
+                List<String> keys = getMasterKeys();
+                
+                String value = StringUtils.substringBetween(entry.getValue(), "cryptex[", "]");
+                String [] cryptex = value.split(",");
+                
+                String decryptedValue = null;
+                if (cryptex.length == 1) {
+                    decryptedValue = crypto.decrypt(cryptex[0].trim(), keys.get(0));
+                } else if (cryptex.length == 2) {
+                    decryptedValue = crypto.decrypt(cryptex[0].trim(), keys.get(Integer.valueOf(cryptex[1].trim()) - 1));
                 }
-
-                if (StringUtils.isNotBlank(key)) {
-                    final String decryptedText = crypto.decrypt(StringUtils.substringBetween(entry.getValue(), "cryptex[", "]"), key);
-                    if (StringUtils.isNotBlank(decryptedText)) {
-                        this.values.put(entry.getKey(), decryptedText);
-                    } else {
-                        decrypted = false;
-                    }
+                
+                if (StringUtils.isNotBlank(decryptedValue)) {
+                    this.values.put(entry.getKey(), decryptedValue);
                 } else {
-                    LOG.error("Found encrypted config value '" + entry.getKey() + "' but no masterkey was set.");
-                    decrypted = false;
+                    LOG.error("Failed to decrypt a config value");
+                    this.decrypted = false;
                 }
             }
         }
@@ -164,22 +168,26 @@ public boolean isDecrypted() {
     /**
      * @return The master key for encrypted config value, returns a default value if in test mode
      */
-    public String getMasterKey() {
+    public List<String> getMasterKeys() {
         String masterkey = System.getProperty(Jvm.APPLICATION_MASTERKEY.toString());
-        if (StringUtils.isBlank(masterkey)) {
+        List<String> keys = new ArrayList<>();
+        
+        if (StringUtils.isNotBlank(masterkey)) {
+            keys.add(masterkey);
+        } else {
             String masterkeyFile = this.values.get(Key.APPLICATION_MASTERKEY_FILE.toString());
             if (StringUtils.isNotBlank(masterkeyFile)) {
                 try {
-                    masterkey = FileUtils.readFileToString(new File(masterkeyFile), Default.ENCODING.toString()); //NOSONAR
-                } catch (final IOException e) {
-                    LOG.error("Failed to read master key", e);
+                    keys = FileUtils.readLines(new File(masterkeyFile), Default.ENCODING.toString());
+                } catch (IOException e) {
+                    LOG.error("Failed to load masterkey file. Please make sure to set a masterkey file if using encrypted config values");
                 }
             } else {
                 LOG.error("Failed to load masterkey file. Please make sure to set a masterkey file if using encrypted config values");
-            }
+            }  
         }
 
-        return masterkey;
+        return keys;
     }
 
     /**
diff --git a/mangooio-integration-test/key/masterkey.txt b/mangooio-integration-test/key/masterkey.txt
index 0e309832f0..3e3c0c8188 100644
--- a/mangooio-integration-test/key/masterkey.txt
+++ b/mangooio-integration-test/key/masterkey.txt
@@ -1 +1,3 @@
-jkldjsaklKJSjskadsjkalcxynkjlds2
\ No newline at end of file
+jkldjsaklKJSjskadsjkalcxynkjlds2
+jlkfsajkbfahjbfsakbfjsakbfsjakbf
+njkfd2b2hwbdsajdsajkdsnajkdsakjc
\ No newline at end of file
diff --git a/mangooio-integration-test/src/main/resources/application.yaml b/mangooio-integration-test/src/main/resources/application.yaml
index 6d50aaf7be..9fda59a70a 100644
--- a/mangooio-integration-test/src/main/resources/application.yaml
+++ b/mangooio-integration-test/src/main/resources/application.yaml
@@ -70,6 +70,8 @@ test:
     application:
         masterkeyfile    : ./key/masterkey.txt
         foo              : cryptex[MloJcu6/zaaNs7gfpfZATg==]
+        bar              : cryptex[NtUQaVGVUAVoTsl2c1HMDw==, 2]  
+        foobar           : cryptex[WqfTFTyaEW2umq5d47Twow==, 3]               
         admin:
               enable     : true
               username   : cryptex[MloJcu6/zaaNs7gfpfZATg==]
diff --git a/mangooio-integration-test/src/test/java/io/mangoo/configuration/ConfigTest.java b/mangooio-integration-test/src/test/java/io/mangoo/configuration/ConfigTest.java
index 37a08c0049..61a1a027f7 100644
--- a/mangooio-integration-test/src/test/java/io/mangoo/configuration/ConfigTest.java
+++ b/mangooio-integration-test/src/test/java/io/mangoo/configuration/ConfigTest.java
@@ -132,6 +132,24 @@ public void testEncryptedValue() {
         assertThat(config.getString("application.foo"), equalTo("admin"));
     }
     
+    @Test
+    public void testEncryptedValueMultiKeyLineTwo() {
+        //given
+        final Config config = Application.getInstance(Config.class);
+
+        //then
+        assertThat(config.getString("application.bar"), equalTo("westeros"));
+    }
+    
+    @Test
+    public void testEncryptedValueMultiKeyLineThree() {
+        //given
+        final Config config = Application.getInstance(Config.class);
+
+        //then
+        assertThat(config.getString("application.foobar"), equalTo("essos"));
+    }
+    
     @Test
     public void testGetMasterKey() {
         //given
@@ -139,7 +157,7 @@ public void testGetMasterKey() {
         System.setProperty(Jvm.APPLICATION_MASTERKEY.toString(), "thisismymasterkey");
 
         //then
-        assertThat(config.getMasterKey(), equalTo("thisismymasterkey"));
+        assertThat(config.getMasterKeys().get(0), equalTo("thisismymasterkey"));
     }
     
     @Test
diff --git a/pom.xml b/pom.xml
index 00fb678869..d59ea5255a 100644
--- a/pom.xml
+++ b/pom.xml
@@ -25,7 +25,7 @@
 		<project.build.sourceEncoding>UTF-8</project.build.sourceEncoding>
 		<log4j.version>2.10.0</log4j.version>
 		<maven.version>3.5.2</maven.version>
-		<httpcomponents.version>4.5.4</httpcomponents.version>
+		<httpcomponents.version>4.5.5</httpcomponents.version>
 		<scribejava.version>5.1.0</scribejava.version>
 		<jackson.version>2.9.3</jackson.version>
 		<fluentlenium.version>3.4.1</fluentlenium.version>
@@ -210,7 +210,7 @@
 			<dependency>
 				<groupId>org.apache.maven.plugin-tools</groupId>
 				<artifactId>maven-plugin-annotations</artifactId>
-				<version>3.5</version>
+				<version>3.5.1</version>
 			</dependency>
 			<dependency>
 				<groupId>io.jsonwebtoken</groupId>