diff --git a/jOOQ/src/main/java/org/jooq/InsertOnDuplicateStep.java b/jOOQ/src/main/java/org/jooq/InsertOnDuplicateStep.java
index 8883db4849..f73a6c8c94 100644
--- a/jOOQ/src/main/java/org/jooq/InsertOnDuplicateStep.java
+++ b/jOOQ/src/main/java/org/jooq/InsertOnDuplicateStep.java
@@ -39,6 +39,7 @@ package org.jooq;
 
 import static org.jooq.SQLDialect.CUBRID;
 // ...
+import static org.jooq.SQLDialect.H2;
 import static org.jooq.SQLDialect.HSQLDB;
 // ...
 import static org.jooq.SQLDialect.MARIADB;
@@ -123,9 +124,9 @@ public interface InsertOnDuplicateStep<R extends Record> extends InsertReturning
      * {@link DSLContext#mergeInto(Table)}).</li>
      * </ul>
      * <p>
-     * These are the dialects that fulfill the above requirements:
+     * H2 supports this clause in MySQL mode.
      */
-    @Support({ CUBRID, HSQLDB, MARIADB, MYSQL, POSTGRES_9_5 })
+    @Support({ CUBRID, H2, HSQLDB, MARIADB, MYSQL, POSTGRES_9_5 })
     InsertOnDuplicateSetStep<R> onDuplicateKeyUpdate();
 
     /**
diff --git a/jOOQ/src/main/java/org/jooq/InsertQuery.java b/jOOQ/src/main/java/org/jooq/InsertQuery.java
index 3c9fe2fe32..73612049fa 100644
--- a/jOOQ/src/main/java/org/jooq/InsertQuery.java
+++ b/jOOQ/src/main/java/org/jooq/InsertQuery.java
@@ -154,7 +154,7 @@ public interface InsertQuery<R extends Record> extends StoreQuery<R>, Insert<R>
      *
      * @see InsertOnDuplicateStep#onDuplicateKeyUpdate()
      */
-    @Support({ CUBRID, HSQLDB, MARIADB, MYSQL, POSTGRES_9_5 })
+    @Support({ CUBRID, H2, HSQLDB, MARIADB, MYSQL, POSTGRES_9_5 })
     void onDuplicateKeyUpdate(boolean flag);
 
     /**
@@ -218,7 +218,7 @@ public interface InsertQuery<R extends Record> extends StoreQuery<R>, Insert<R>
      *
      * @see InsertOnDuplicateStep#onDuplicateKeyUpdate()
      */
-    @Support({ CUBRID, HSQLDB, MARIADB, MYSQL, POSTGRES_9_5 })
+    @Support({ CUBRID, H2, HSQLDB, MARIADB, MYSQL, POSTGRES_9_5 })
     <T> void addValueForUpdate(Field<T> field, T value);
 
     /**
@@ -227,7 +227,7 @@ public interface InsertQuery<R extends Record> extends StoreQuery<R>, Insert<R>
      *
      * @see InsertOnDuplicateStep#onDuplicateKeyUpdate()
      */
-    @Support({ CUBRID, HSQLDB, MARIADB, MYSQL, POSTGRES_9_5 })
+    @Support({ CUBRID, H2, HSQLDB, MARIADB, MYSQL, POSTGRES_9_5 })
     <T> void addValueForUpdate(Field<T> field, Field<T> value);
 
     /**
@@ -240,7 +240,7 @@ public interface InsertQuery<R extends Record> extends StoreQuery<R>, Insert<R>
      *
      * @see InsertOnDuplicateStep#onDuplicateKeyUpdate()
      */
-    @Support({ CUBRID, HSQLDB, MARIADB, MYSQL, POSTGRES_9_5 })
+    @Support({ CUBRID, H2, HSQLDB, MARIADB, MYSQL, POSTGRES_9_5 })
     void addValuesForUpdate(Map<?, ?> map);
 
     /**
diff --git a/jOOQ/src/main/java/org/jooq/impl/InsertQueryImpl.java b/jOOQ/src/main/java/org/jooq/impl/InsertQueryImpl.java
index 0d836038e6..cb1e6f8d6c 100644
--- a/jOOQ/src/main/java/org/jooq/impl/InsertQueryImpl.java
+++ b/jOOQ/src/main/java/org/jooq/impl/InsertQueryImpl.java
@@ -44,6 +44,7 @@ import static org.jooq.Clause.INSERT_ON_DUPLICATE_KEY_UPDATE;
 import static org.jooq.Clause.INSERT_ON_DUPLICATE_KEY_UPDATE_ASSIGNMENT;
 import static org.jooq.Clause.INSERT_RETURNING;
 import static org.jooq.Clause.INSERT_SELECT;
+import static org.jooq.SQLDialect.H2;
 import static org.jooq.SQLDialect.MARIADB;
 import static org.jooq.SQLDialect.MYSQL;
 // ...
@@ -256,15 +257,26 @@ final class InsertQueryImpl<R extends Record> extends AbstractStoreQuery<R> impl
 
                 // MySQL has a nice syntax for this
                 case CUBRID:
+                case H2:
                 case MARIADB:
                 case MYSQL: {
+
+                    // [#2508] In H2, this syntax is supported in MySQL MODE (we're assuming users will
+                    //         set this mode in order to profit from this functionality). Up until
+                    //         H2 1.4.197, qualification of columns in the ON DUPLICATE KEY UPDATE clause
+                    //         wasn't supported (see https://github.com/h2database/h2database/issues/1027)
+                    boolean oldQualify = ctx.qualify();
+                    boolean newQualify = ctx.family() == H2 ? false : oldQualify;
+
                     toSQLInsert(ctx);
                     ctx.formatSeparator()
                        .start(INSERT_ON_DUPLICATE_KEY_UPDATE)
                        .visit(K_ON_DUPLICATE_KEY_UPDATE)
                        .formatIndentStart()
                        .formatSeparator()
+                       .qualify(newQualify)
                        .visit(updateMap)
+                       .qualify(oldQualify)
                        .formatIndentEnd()
                        .end(INSERT_ON_DUPLICATE_KEY_UPDATE);
 
@@ -330,11 +342,6 @@ final class InsertQueryImpl<R extends Record> extends AbstractStoreQuery<R> impl
                     break;
                 }
 
-                // Some dialects can't really handle this clause. Emulation should be done in two steps
-                case H2: {
-                    throw new SQLDialectNotSupportedException("The ON DUPLICATE KEY UPDATE clause cannot be emulated for " + ctx.dialect());
-                }
-
                 // Some databases allow for emulating this clause using a MERGE statement