diff --git a/LICENSE b/LICENSE
index d703157e..126ceb1a 100644
--- a/LICENSE
+++ b/LICENSE
@@ -1,6 +1,6 @@
 MIT License
 
-Copyright (C) 2024, Twilio SendGrid, Inc. <help@twilio.com>
+Copyright (C) 2025, Twilio SendGrid, Inc. <help@twilio.com>
 
 Permission is hereby granted, free of charge, to any person obtaining a copy of
 this software and associated documentation files (the "Software"), to deal in
diff --git a/pom.xml b/pom.xml
index dad3a41a..bc9110ad 100644
--- a/pom.xml
+++ b/pom.xml
@@ -20,7 +20,7 @@
     </license>
   </licenses>
   <properties>
-    <jackson.version>2.14.0</jackson.version>
+    <jackson.version>2.19.0</jackson.version>
   </properties>
   <scm>
     <url>https://github.com/sendgrid/sendgrid-java</url>
@@ -100,7 +100,7 @@
           <plugin>
             <groupId>org.apache.maven.plugins</groupId>
             <artifactId>maven-shade-plugin</artifactId>
-            <version>3.2.4</version>
+            <version>3.6.0</version>
             <configuration>
               <relocations>
                 <relocation>
@@ -145,8 +145,8 @@
         <artifactId>maven-compiler-plugin</artifactId>
         <version>3.8.1</version>
         <configuration>
-          <source>1.8</source>
-          <target>1.8</target>
+          <source>21</source>
+          <target>21</target>
         </configuration>
       </plugin>
       <plugin>
@@ -209,7 +209,7 @@
       <plugin>
         <groupId>org.apache.maven.plugins</groupId>
         <artifactId>maven-shade-plugin</artifactId>
-        <version>3.2.4</version>
+        <version>3.6.0</version>
         <configuration>
           <relocations>
             <relocation>
@@ -262,7 +262,7 @@
     <dependency>
       <groupId>com.sendgrid</groupId>
       <artifactId>java-http-client</artifactId>
-      <version>4.5.0</version>
+      <version>4.5.1</version>
     </dependency>
     <dependency>
       <groupId>com.fasterxml.jackson.core</groupId>
diff --git a/src/main/java/com/sendgrid/helpers/mail/Mail.java b/src/main/java/com/sendgrid/helpers/mail/Mail.java
index ea2b9739..7fd9ec4a 100644
--- a/src/main/java/com/sendgrid/helpers/mail/Mail.java
+++ b/src/main/java/com/sendgrid/helpers/mail/Mail.java
@@ -117,6 +117,10 @@ public class Mail {
   @JsonProperty("reply_to")
   public Email replyTo;
 
+  /** The email's list of reply to addresses. */
+  @JsonProperty("reply_to_list")
+  public List<Email> replyToList;
+
   private static final ObjectMapper SORTED_MAPPER = new ObjectMapper();
 
   static {
@@ -505,6 +509,32 @@ public void setReplyTo(Email replyTo) {
     this.replyTo = replyTo;
   }
 
+  /**
+   * Get the email's reply to list.
+   *
+   * @return the reply to list.
+   */
+  @JsonProperty("reply_to_list")
+  public List<Email> getReplyToList() { return replyToList; }
+
+  /**
+   * Set the email's reply to list addresses.
+   *
+   * @param replyToList a list of reply to address.
+   */
+  public void setReplyTo(List<Email> replyToList) {
+    this.replyToList = replyToList;
+  }
+
+  /**
+   * Add a reply to address to the list.
+   *
+   * @param replyTo a reply to address.
+   */
+  public void addReplyTo(Email replyTo) {
+    this.replyToList = addToList(replyTo, this.replyToList);
+  }
+
   /**
    * Create a string representation of the Mail object JSON.
    *