diff --git a/extensions/guacamole-auth-ldap/src/main/java/org/apache/guacamole/auth/ldap/conf/CaseInsensitivePatternDeserializer.java b/extensions/guacamole-auth-ldap/src/main/java/org/apache/guacamole/auth/ldap/conf/CaseInsensitivePatternDeserializer.java
new file mode 100644
index 000000000..0525b1dbe
--- /dev/null
+++ b/extensions/guacamole-auth-ldap/src/main/java/org/apache/guacamole/auth/ldap/conf/CaseInsensitivePatternDeserializer.java
@@ -0,0 +1,81 @@
+/*
+ * Licensed to the Apache Software Foundation (ASF) under one
+ * or more contributor license agreements.  See the NOTICE file
+ * distributed with this work for additional information
+ * regarding copyright ownership.  The ASF licenses this file
+ * to you under the Apache License, Version 2.0 (the
+ * "License"); you may not use this file except in compliance
+ * with the License.  You may obtain a copy of the License at
+ *
+ *   http://www.apache.org/licenses/LICENSE-2.0
+ *
+ * Unless required by applicable law or agreed to in writing,
+ * software distributed under the License is distributed on an
+ * "AS IS" BASIS, WITHOUT WARRANTIES OR CONDITIONS OF ANY
+ * KIND, either express or implied.  See the License for the
+ * specific language governing permissions and limitations
+ * under the License.
+ */
+
+package org.apache.guacamole.auth.ldap.conf;
+
+import com.fasterxml.jackson.core.JsonParseException;
+import com.fasterxml.jackson.core.JsonParser;
+import com.fasterxml.jackson.core.JsonProcessingException;
+import com.fasterxml.jackson.core.JsonToken;
+import com.fasterxml.jackson.databind.DeserializationContext;
+import com.fasterxml.jackson.databind.deser.std.StdScalarDeserializer;
+import com.fasterxml.jackson.databind.type.LogicalType;
+import java.io.IOException;
+import java.io.Serializable;
+import java.util.regex.Pattern;
+import java.util.regex.PatternSyntaxException;
+
+/**
+ * Custom JSON (or YAML) deserializer for Jackson that deserializes string
+ * values as Patterns with the case insensitive flag set by default. Jackson
+ * will actually handle deserialization of Patterns automatically, but does not
+ * provide for setting the default flags.
+ */
+public class CaseInsensitivePatternDeserializer extends StdScalarDeserializer<Pattern> {
+
+    /**
+     * Unique version identifier of this {@link Serializable} class.
+     */
+    private static final long serialVersionUID = 1L;
+
+    /**
+     * Creates a new CaseInsensitivePatternDeserializer which deserializes
+     * string values to Pattern objects with the case insensitive flag set.
+     */
+    public CaseInsensitivePatternDeserializer() {
+        super(Pattern.class);
+    }
+
+    @Override
+    public LogicalType logicalType() {
+        return LogicalType.Textual;
+    }
+
+    @Override
+    public boolean isCachable() {
+        return true;
+    }
+
+    @Override
+    public Pattern deserialize(JsonParser parser, DeserializationContext context)
+            throws IOException, JsonProcessingException {
+
+        if (!parser.hasToken(JsonToken.VALUE_STRING))
+            throw new JsonParseException(parser, "Regular expressions may only be represented as strings.");
+
+        try {
+            return Pattern.compile(parser.getText(), Pattern.CASE_INSENSITIVE);
+        }
+        catch (PatternSyntaxException e) {
+            throw new JsonParseException(parser, "Invalid regular expression.", e);
+        }
+
+    }
+
+}
diff --git a/extensions/guacamole-auth-ldap/src/main/java/org/apache/guacamole/auth/ldap/conf/ConfigurationService.java b/extensions/guacamole-auth-ldap/src/main/java/org/apache/guacamole/auth/ldap/conf/ConfigurationService.java
index fab1a7027..f1e560ec1 100644
--- a/extensions/guacamole-auth-ldap/src/main/java/org/apache/guacamole/auth/ldap/conf/ConfigurationService.java
+++ b/extensions/guacamole-auth-ldap/src/main/java/org/apache/guacamole/auth/ldap/conf/ConfigurationService.java
@@ -21,6 +21,7 @@ package org.apache.guacamole.auth.ldap.conf;
 
 import com.fasterxml.jackson.core.type.TypeReference;
 import com.fasterxml.jackson.databind.ObjectMapper;
+import com.fasterxml.jackson.databind.module.SimpleModule;
 import com.fasterxml.jackson.dataformat.yaml.YAMLFactory;
 import com.google.inject.Inject;
 import com.google.inject.Singleton;
@@ -29,6 +30,7 @@ import java.io.IOException;
 import java.util.Collection;
 import java.util.Collections;
 import java.util.concurrent.atomic.AtomicLong;
+import java.util.regex.Pattern;
 import org.apache.guacamole.GuacamoleException;
 import org.apache.guacamole.GuacamoleServerException;
 import org.apache.guacamole.environment.Environment;
@@ -49,7 +51,8 @@ public class ConfigurationService {
     /**
      * ObjectMapper for deserializing YAML.
      */
-    private final ObjectMapper mapper = new ObjectMapper(new YAMLFactory());
+    private final ObjectMapper mapper = new ObjectMapper(new YAMLFactory())
+            .registerModule(new SimpleModule().addDeserializer(Pattern.class, new CaseInsensitivePatternDeserializer()));
 
     /**
      * The name of the file within GUACAMOLE_HOME that defines each available