diff --git a/hibernate-core/src/main/java/org/hibernate/type/descriptor/java/LocalDateTimeJavaDescriptor.java b/hibernate-core/src/main/java/org/hibernate/type/descriptor/java/LocalDateTimeJavaDescriptor.java
index 1760393c25..aa3c760fef 100644
--- a/hibernate-core/src/main/java/org/hibernate/type/descriptor/java/LocalDateTimeJavaDescriptor.java
+++ b/hibernate-core/src/main/java/org/hibernate/type/descriptor/java/LocalDateTimeJavaDescriptor.java
@@ -55,8 +55,14 @@ public class LocalDateTimeJavaDescriptor extends AbstractTypeDescriptor<LocalDat
 		}
 
 		if ( java.sql.Timestamp.class.isAssignableFrom( type ) ) {
-			Instant instant = value.atZone( ZoneId.systemDefault() ).toInstant();
-			return (X) java.sql.Timestamp.from( instant );
+			/*
+			 * Workaround for HHH-13266 (JDK-8061577).
+			 * We used to do Timestamp.from( value.atZone( ZoneId.systemDefault() ).toInstant() ),
+			 * but on top of being more complex than the line below, it won't always work.
+			 * Timestamp.from() assumes the number of milliseconds since the epoch
+			 * means the same thing in Timestamp and Instant, but it doesn't, in particular before 1900.
+			 */
+			return (X) Timestamp.valueOf( value );
 		}
 
 		if ( java.sql.Date.class.isAssignableFrom( type ) ) {
@@ -98,7 +104,14 @@ public class LocalDateTimeJavaDescriptor extends AbstractTypeDescriptor<LocalDat
 
 		if ( Timestamp.class.isInstance( value ) ) {
 			final Timestamp ts = (Timestamp) value;
-			return LocalDateTime.ofInstant( ts.toInstant(), ZoneId.systemDefault() );
+			/*
+			 * Workaround for HHH-13266 (JDK-8061577).
+			 * We used to do LocalDateTime.ofInstant( ts.toInstant(), ZoneId.systemDefault() ),
+			 * but on top of being more complex than the line below, it won't always work.
+			 * ts.toInstant() assumes the number of milliseconds since the epoch
+			 * means the same thing in Timestamp and Instant, but it doesn't, in particular before 1900.
+			 */
+			return ts.toLocalDateTime();
 		}
 
 		if ( Long.class.isInstance( value ) ) {