diff --git a/pom.xml b/pom.xml
index 6f315ad8f4..98dd6a91e8 100644
--- a/pom.xml
+++ b/pom.xml
@@ -88,8 +88,9 @@
         <jackson.annotations.version>${jackson.version}</jackson.annotations.version>
 
         <!--JAKARTA-->
-        <com.sun.jakarta.mail.version>2.0.1</com.sun.jakarta.mail.version>
         <jakarta.persistence.version>3.1.0</jakarta.persistence.version>
+        <jakarta.mail.version>2.1.1</jakarta.mail.version>
+        <angus.mail.version>2.0.1</angus.mail.version>
         <jakarta.servlet.version>6.0.0</jakarta.servlet.version>
         <jakarta.ws.rs.version>3.1.0</jakarta.ws.rs.version>
         <jakarta.xml.ws.version>4.0.0</jakarta.xml.ws.version>
@@ -175,7 +176,7 @@
         <oracle-jdbc.version>21.5.0.0</oracle-jdbc.version>
 
         <!-- Test -->
-        <greenmail.version>2.0.0-alpha-3</greenmail.version>
+        <greenmail.version>2.1.0-alpha-1</greenmail.version>
         <hamcrest.version>2.2</hamcrest.version>
         <jmeter.version>2.10</jmeter.version>
         <junit.version>4.13.2</junit.version>
@@ -426,9 +427,15 @@
 
             <!--JAKARTA-->
             <dependency>
-                <groupId>com.sun.mail</groupId>
-                <artifactId>jakarta.mail</artifactId>
-                <version>${com.sun.jakarta.mail.version}</version>
+                <groupId>jakarta.mail</groupId>
+                <artifactId>jakarta.mail-api</artifactId>
+                <version>${jakarta.mail.version}</version>
+            </dependency>
+            <!--Implementation of the Jakarta Mail API-->
+            <dependency>
+                <groupId>org.eclipse.angus</groupId>
+                <artifactId>angus-mail</artifactId>
+                <version>${angus.mail.version}</version>
             </dependency>
             <dependency>
                 <groupId>jakarta.ws.rs</groupId>
diff --git a/quarkus/runtime/pom.xml b/quarkus/runtime/pom.xml
index 0ead7c82bc..aec085780b 100644
--- a/quarkus/runtime/pom.xml
+++ b/quarkus/runtime/pom.xml
@@ -584,8 +584,12 @@
             </exclusions>
         </dependency>
         <dependency>
-            <groupId>com.sun.mail</groupId>
-            <artifactId>jakarta.mail</artifactId>
+            <groupId>jakarta.mail</groupId>
+            <artifactId>jakarta.mail-api</artifactId>
+        </dependency>
+        <dependency>
+            <groupId>org.eclipse.angus</groupId>
+            <artifactId>angus-mail</artifactId>
         </dependency>
         <dependency>
             <groupId>org.apache.santuario</groupId>
diff --git a/services/pom.xml b/services/pom.xml
index 75141773f2..088303caa5 100755
--- a/services/pom.xml
+++ b/services/pom.xml
@@ -56,8 +56,12 @@
             <scope>provided</scope>
         </dependency>
         <dependency>
-            <groupId>com.sun.mail</groupId>
-            <artifactId>jakarta.mail</artifactId>
+            <groupId>jakarta.mail</groupId>
+            <artifactId>jakarta.mail-api</artifactId>
+        </dependency>
+        <dependency>
+            <groupId>org.eclipse.angus</groupId>
+            <artifactId>angus-mail</artifactId>
         </dependency>
         <dependency>
             <groupId>org.keycloak</groupId>
diff --git a/services/src/main/java/org/keycloak/email/DefaultEmailSenderProvider.java b/services/src/main/java/org/keycloak/email/DefaultEmailSenderProvider.java
index 2bbf006e7d..102ae77092 100644
--- a/services/src/main/java/org/keycloak/email/DefaultEmailSenderProvider.java
+++ b/services/src/main/java/org/keycloak/email/DefaultEmailSenderProvider.java
@@ -17,7 +17,7 @@
 
 package org.keycloak.email;
 
-import com.sun.mail.smtp.SMTPMessage;
+import jakarta.mail.internet.MimeUtility;
 import org.jboss.logging.Logger;
 import org.keycloak.models.KeycloakSession;
 import org.keycloak.models.UserModel;
@@ -30,18 +30,23 @@ import jakarta.mail.Address;
 import jakarta.mail.MessagingException;
 import jakarta.mail.Multipart;
 import jakarta.mail.Session;
+import jakarta.mail.Message;
 import jakarta.mail.Transport;
 import jakarta.mail.internet.AddressException;
 import jakarta.mail.internet.InternetAddress;
 import jakarta.mail.internet.MimeBodyPart;
 import jakarta.mail.internet.MimeMultipart;
+import jakarta.mail.internet.MimeMessage;
 import javax.net.ssl.SSLContext;
 import javax.net.ssl.SSLSocketFactory;
 import java.io.UnsupportedEncodingException;
+import java.nio.charset.StandardCharsets;
 import java.util.Date;
 import java.util.Map;
 import java.util.Properties;
 
+import static org.keycloak.utils.StringUtil.isNotBlank;
+
 /**
  * @author <a href="mailto:sthorger@redhat.com">Stian Thorgersen</a>
  */
@@ -123,19 +128,21 @@ public class DefaultEmailSenderProvider implements EmailSenderProvider {
                 multipart.addBodyPart(htmlPart);
             }
 
-            SMTPMessage msg = new SMTPMessage(session);
+            Message msg = new MimeMessage(session);
             msg.setFrom(toInternetAddress(from, fromDisplayName));
 
             msg.setReplyTo(new Address[]{toInternetAddress(from, fromDisplayName)});
-            if (replyTo != null && !replyTo.isEmpty()) {
+
+            if (isNotBlank(replyTo)) {
                 msg.setReplyTo(new Address[]{toInternetAddress(replyTo, replyToDisplayName)});
             }
-            if (envelopeFrom != null && !envelopeFrom.isEmpty()) {
-                msg.setEnvelopeFrom(envelopeFrom);
+
+            if (isNotBlank(envelopeFrom)) {
+                props.setProperty("mail.smtp.from", envelopeFrom);
             }
 
             msg.setHeader("To", address);
-            msg.setSubject(subject, "utf-8");
+            msg.setSubject(MimeUtility.encodeText(subject, StandardCharsets.UTF_8.name(), null));
             msg.setContent(multipart);
             msg.saveChanges();
             msg.setSentDate(new Date());
diff --git a/testsuite/utils/pom.xml b/testsuite/utils/pom.xml
index 8dd6f140a9..a47a1dfa3c 100755
--- a/testsuite/utils/pom.xml
+++ b/testsuite/utils/pom.xml
@@ -36,8 +36,12 @@
 
     <dependencies>
         <dependency>
-            <groupId>com.sun.mail</groupId>
-            <artifactId>jakarta.mail</artifactId>
+            <groupId>jakarta.mail</groupId>
+            <artifactId>jakarta.mail-api</artifactId>
+        </dependency>
+        <dependency>
+            <groupId>org.eclipse.angus</groupId>
+            <artifactId>angus-mail</artifactId>
         </dependency>
         <dependency>
             <groupId>org.bouncycastle</groupId>
@@ -285,7 +289,6 @@
             <artifactId>mssql-jdbc</artifactId>
             <version>${mssql-jdbc.version}</version>
         </dependency>
-
     </dependencies>