diff --git a/CHANGELOG.md b/CHANGELOG.md
index 821adfa63433e..26b4287f0ab0b 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -22,6 +22,7 @@ The format is based on [Keep a Changelog](https://keepachangelog.com/en/1.0.0/),
 - Onboarding new maven snapshots publishing to s3 ([#19619](https://github.com/opensearch-project/OpenSearch/pull/19619))
 - Remove MultiCollectorWrapper and use MultiCollector in Lucene instead ([#19595](https://github.com/opensearch-project/OpenSearch/pull/19595))
 - Change implementation for `percentiles` aggregation for latency improvement ([#19648](https://github.com/opensearch-project/OpenSearch/pull/19648))
+- Wrap checked exceptions in painless.DefBootstrap to support JDK-25 ([#19706](https://github.com/opensearch-project/OpenSearch/pull/19706))
 - Refactor the ThreadPoolStats.Stats class to use the Builder pattern instead of constructors ([#19306](https://github.com/opensearch-project/OpenSearch/pull/19306))
 
 ### Fixed
diff --git a/modules/lang-painless/src/main/java/org/opensearch/painless/DefBootstrap.java b/modules/lang-painless/src/main/java/org/opensearch/painless/DefBootstrap.java
index 0726881b1297f..89d3d62baf714 100644
--- a/modules/lang-painless/src/main/java/org/opensearch/painless/DefBootstrap.java
+++ b/modules/lang-painless/src/main/java/org/opensearch/painless/DefBootstrap.java
@@ -112,6 +112,17 @@ private DefBootstrap() {} // no instance!
      */
     public static final int OPERATOR_EXPLICIT_CAST = 1 << 2;
 
+    /**
+     * ClassValue.getFromHashMap will wrap checked exceptions with Errors. To get
+     * around that we wrap any checked exceptions with this RuntimeException and
+     * unwrap them later.
+     */
+    static final class WrappedCheckedException extends RuntimeException {
+        private WrappedCheckedException(Exception cause) {
+            super(cause);
+        }
+    }
+
     /**
      * CallSite that implements the polymorphic inlining cache (PIC).
      */
@@ -204,7 +215,10 @@ protected MethodHandle computeValue(Class<?> receiverType) {
                     try {
                         return lookup(flavor, name, receiverType).asType(type);
                     } catch (Throwable t) {
-                        Def.rethrow(t);
+                        switch (t) {
+                            case Exception e -> throw new WrappedCheckedException(e);
+                            default -> Def.rethrow(t);
+                        }
                         throw new AssertionError();
                     }
                 }
diff --git a/modules/lang-painless/src/main/java/org/opensearch/painless/PainlessScript.java b/modules/lang-painless/src/main/java/org/opensearch/painless/PainlessScript.java
index 766d9baaa0b1a..885282cead156 100644
--- a/modules/lang-painless/src/main/java/org/opensearch/painless/PainlessScript.java
+++ b/modules/lang-painless/src/main/java/org/opensearch/painless/PainlessScript.java
@@ -65,14 +65,18 @@ public interface PainlessScript {
     /**
      * Adds stack trace and other useful information to exceptions thrown
      * from a Painless script.
-     * @param t The throwable to build an exception around.
+     * @param originalThrowable The throwable to build an exception around.
      * @return The generated ScriptException.
      */
-    default ScriptException convertToScriptException(Throwable t, Map<String, List<String>> extraMetadata) {
+    default ScriptException convertToScriptException(Throwable originalThrowable, Map<String, List<String>> extraMetadata) {
+        final Throwable unwrapped = switch (originalThrowable) {
+            case DefBootstrap.WrappedCheckedException w -> w.getCause();
+            default -> originalThrowable;
+        };
         // create a script stack: this is just the script portion
         List<String> scriptStack = new ArrayList<>();
         ScriptException.Position pos = null;
-        for (StackTraceElement element : t.getStackTrace()) {
+        for (StackTraceElement element : unwrapped.getStackTrace()) {
             if (WriterConstants.CLASS_NAME.equals(element.getClassName())) {
                 // found the script portion
                 int originalOffset = element.getLineNumber();
@@ -106,7 +110,14 @@ default ScriptException convertToScriptException(Throwable t, Map<String, List<S
                 scriptStack.add(element.toString());
             }
         }
-        ScriptException scriptException = new ScriptException("runtime error", t, scriptStack, getName(), PainlessScriptEngine.NAME, pos);
+        ScriptException scriptException = new ScriptException(
+            "runtime error",
+            unwrapped,
+            scriptStack,
+            getName(),
+            PainlessScriptEngine.NAME,
+            pos
+        );
         for (Map.Entry<String, List<String>> entry : extraMetadata.entrySet()) {
             scriptException.addMetadata(entry.getKey(), entry.getValue());
         }
diff --git a/modules/lang-painless/src/test/java/org/opensearch/painless/DefBootstrapTests.java b/modules/lang-painless/src/test/java/org/opensearch/painless/DefBootstrapTests.java
index ae860d177cce1..58c1c35f15b42 100644
--- a/modules/lang-painless/src/test/java/org/opensearch/painless/DefBootstrapTests.java
+++ b/modules/lang-painless/src/test/java/org/opensearch/painless/DefBootstrapTests.java
@@ -46,6 +46,8 @@
 import java.util.Collections;
 import java.util.HashMap;
 
+import static org.hamcrest.Matchers.instanceOf;
+
 public class DefBootstrapTests extends OpenSearchTestCase {
     private final PainlessLookup painlessLookup = PainlessLookupBuilder.buildFromAllowlists(Allowlist.BASE_ALLOWLISTS);
 
@@ -157,9 +159,11 @@ public void testMegamorphic() throws Throwable {
         map.put("a", "b");
         assertEquals(2, (int) handle.invokeExact((Object) map));
 
-        final IllegalArgumentException iae = expectThrows(IllegalArgumentException.class, () -> {
+        final DefBootstrap.WrappedCheckedException wrapped = expectThrows(DefBootstrap.WrappedCheckedException.class, () -> {
             Integer.toString((int) handle.invokeExact(new Object()));
         });
+        assertThat(wrapped.getCause(), instanceOf(IllegalArgumentException.class));
+        final IllegalArgumentException iae = (IllegalArgumentException) wrapped.getCause();
         assertEquals("dynamic method [java.lang.Object, size/0] not found", iae.getMessage());
         assertTrue("Does not fail inside ClassValue.computeValue()", Arrays.stream(iae.getStackTrace()).anyMatch(e -> {
             return e.getMethodName().equals("computeValue") && e.getClassName().startsWith("org.opensearch.painless.DefBootstrap$PIC$");