diff --git a/bom/pom.xml b/bom/pom.xml
index 3fc576fae329a..bc95cdf69a126 100644
--- a/bom/pom.xml
+++ b/bom/pom.xml
@@ -319,11 +319,6 @@ THE SOFTWARE.
         <artifactId>symbol-annotation</artifactId>
         <version>1.1</version>
       </dependency>
-      <dependency>
-        <groupId>com.sun.mail</groupId>
-        <artifactId>jakarta.mail</artifactId>
-        <version>1.6.5</version>
-      </dependency>
 
       <!--XStream-->
       <dependency>
diff --git a/core/pom.xml b/core/pom.xml
index 0b10a40a0d22f..28fbaaaf812bd 100644
--- a/core/pom.xml
+++ b/core/pom.xml
@@ -280,10 +280,6 @@ THE SOFTWARE.
       <groupId>org.apache.commons</groupId>
       <artifactId>commons-compress</artifactId>
     </dependency>
-    <dependency>
-      <groupId>com.sun.mail</groupId>
-      <artifactId>jakarta.mail</artifactId>
-    </dependency>
     <dependency>
       <groupId>jaxen</groupId>
       <artifactId>jaxen</artifactId>
diff --git a/core/src/main/java/jenkins/model/JenkinsLocationConfiguration.java b/core/src/main/java/jenkins/model/JenkinsLocationConfiguration.java
index 12aa35b0e5f61..b78d5f689e35a 100644
--- a/core/src/main/java/jenkins/model/JenkinsLocationConfiguration.java
+++ b/core/src/main/java/jenkins/model/JenkinsLocationConfiguration.java
@@ -14,12 +14,11 @@
 import hudson.util.XStream2;
 import java.io.File;
 import java.io.IOException;
+import java.io.UncheckedIOException;
 import java.lang.reflect.InvocationTargetException;
 import java.lang.reflect.Method;
 import java.util.logging.Level;
 import java.util.logging.Logger;
-import javax.mail.internet.AddressException;
-import javax.mail.internet.InternetAddress;
 import javax.servlet.ServletContext;
 import jenkins.util.SystemProperties;
 import jenkins.util.UrlHelper;
@@ -211,10 +210,40 @@ public FormValidation doCheckUrl(@QueryParameter String value) {
 
     public FormValidation doCheckAdminAddress(@QueryParameter String value) {
         try {
-            new InternetAddress(value);
+            Class<?> internetAddress = Jenkins.get().pluginManager.uberClassLoader.loadClass("javax.mail.internet.InternetAddress");
+            internetAddress.getDeclaredConstructor(String.class).newInstance(value);
             return FormValidation.ok();
-        } catch (AddressException e) {
-            return FormValidation.error(e.getMessage());
+        } catch (ClassNotFoundException x) {
+            return FormValidation.ok();
+        } catch (NoSuchMethodException x) {
+            NoSuchMethodError e = new NoSuchMethodError(x.getMessage());
+            e.initCause(x);
+            throw e;
+        } catch (IllegalAccessException x) {
+            IllegalAccessError e = new IllegalAccessError(x.getMessage());
+            e.initCause(x);
+            throw e;
+        } catch (InstantiationException x) {
+            InstantiationError e = new InstantiationError(x.getMessage());
+            e.initCause(x);
+            throw e;
+        } catch (InvocationTargetException x) {
+            Throwable t = x.getCause();
+            if (t instanceof RuntimeException) {
+                throw (RuntimeException) t;
+            } else if (t instanceof IOException) {
+                throw new UncheckedIOException((IOException) t);
+            } else if (t instanceof Exception) {
+                if (t.getClass().getName().equals("javax.mail.internet.AddressException")) {
+                    return FormValidation.error(t.getMessage());
+                } else {
+                    throw new RuntimeException(t);
+                }
+            } else if (t instanceof Error) {
+                throw (Error) t;
+            } else {
+                throw new Error(x);
+            }
         }
     }
 
diff --git a/core/src/main/resources/jenkins/split-plugin-cycles.txt b/core/src/main/resources/jenkins/split-plugin-cycles.txt
index 3cec061d7eb09..17f997f98970a 100644
--- a/core/src/main/resources/jenkins/split-plugin-cycles.txt
+++ b/core/src/main/resources/jenkins/split-plugin-cycles.txt
@@ -32,3 +32,5 @@ junit jaxb
 bouncycastle-api jaxb
 command-launcher jaxb
 jdk-tool jaxb
+
+javax-activation-api javax-mail-api
diff --git a/core/src/main/resources/jenkins/split-plugins.txt b/core/src/main/resources/jenkins/split-plugins.txt
index 0bb03189d9c87..eeab9467a13bc 100644
--- a/core/src/main/resources/jenkins/split-plugins.txt
+++ b/core/src/main/resources/jenkins/split-plugins.txt
@@ -34,3 +34,6 @@ trilead-api 2.184 1.0.4
 
 # JENKINS-64107
 sshd 2.281 3.0.1
+
+javax-activation-api 2.328 1.2.0-1
+javax-mail-api 2.328 1.6.2-1
diff --git a/test/pom.xml b/test/pom.xml
index 336a6e6322ed8..e3304968c32c0 100644
--- a/test/pom.xml
+++ b/test/pom.xml
@@ -121,6 +121,12 @@ THE SOFTWARE.
       <version>391.ve4a_38c1b_cf4b_</version>
       <scope>test</scope>
     </dependency>
+    <dependency>
+      <groupId>io.jenkins.plugins</groupId>
+      <artifactId>javax-mail-api</artifactId>
+      <version>1.6.2-1</version>
+      <scope>test</scope>
+    </dependency>
     <dependency>
       <groupId>org.jenkins-ci.plugins</groupId>
       <artifactId>matrix-auth</artifactId>
diff --git a/war/pom.xml b/war/pom.xml
index e71473d30ca03..a9c806ca30e0d 100644
--- a/war/pom.xml
+++ b/war/pom.xml
@@ -367,6 +367,18 @@ THE SOFTWARE.
                   <version>1.0.4</version>
                   <type>hpi</type>
                 </artifactItem>
+                <artifactItem>
+                  <groupId>io.jenkins.plugins</groupId>
+                  <artifactId>javax-activation-api</artifactId>
+                  <version>1.2.0-1</version>
+                  <type>hpi</type>
+                </artifactItem>
+                <artifactItem>
+                  <groupId>io.jenkins.plugins</groupId>
+                  <artifactId>javax-mail-api</artifactId>
+                  <version>1.6.2-1</version>
+                  <type>hpi</type>
+                </artifactItem>
               </artifactItems>
               <outputDirectory>${project.build.directory}/${project.build.finalName}/WEB-INF/detached-plugins</outputDirectory>
               <stripVersion>true</stripVersion>