diff --git a/jOOQ/src/main/java/org/jooq/MergeMatchedThenStep.java b/jOOQ/src/main/java/org/jooq/MergeMatchedThenStep.java
new file mode 100644
index 0000000000..068f6d5a36
--- /dev/null
+++ b/jOOQ/src/main/java/org/jooq/MergeMatchedThenStep.java
@@ -0,0 +1,93 @@
+/*
+ * Licensed under the Apache License, Version 2.0 (the "License");
+ * you may not use this file except in compliance with the License.
+ * You may obtain a copy of the License at
+ *
+ *  http://www.apache.org/licenses/LICENSE-2.0
+ *
+ * Unless required by applicable law or agreed to in writing, software
+ * distributed under the License is distributed on an "AS IS" BASIS,
+ * WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+ * See the License for the specific language governing permissions and
+ * limitations under the License.
+ *
+ * Other licenses:
+ * -----------------------------------------------------------------------------
+ * Commercial licenses for this work are available. These replace the above
+ * ASL 2.0 and offer limited warranties, support, maintenance, and commercial
+ * database integrations.
+ *
+ * For more information, please visit: http://www.jooq.org/licenses
+ *
+ *
+ *
+ *
+ *
+ *
+ *
+ *
+ *
+ *
+ *
+ *
+ *
+ *
+ *
+ *
+ */
+package org.jooq;
+
+// ...
+import static org.jooq.SQLDialect.DERBY;
+import static org.jooq.SQLDialect.H2;
+import static org.jooq.SQLDialect.HSQLDB;
+// ...
+// ...
+// ...
+
+/**
+ * This type is used for the {@link Merge}'s DSL API.
+ * <p>
+ * Example: <code><pre>
+ * DSLContext create = DSL.using(configuration);
+ *
+ * create.mergeInto(table)
+ *       .using(select)
+ *       .on(condition)
+ *       .whenMatchedThenUpdate()
+ *       .set(field1, value1)
+ *       .set(field2, value2)
+ *       .whenNotMatchedThenInsert(field1, field2)
+ *       .values(value1, value2)
+ *       .execute();
+ * </pre></code>
+ * <p>
+ * <h3>Referencing <code>XYZ*Step</code> types directly from client code</h3>
+ * <p>
+ * It is usually not recommended to reference any <code>XYZ*Step</code> types
+ * directly from client code, or assign them to local variables. When writing
+ * dynamic SQL, creating a statement's components dynamically, and passing them
+ * to the DSL API statically is usually a better choice. See the manual's
+ * section about dynamic SQL for details: <a href=
+ * "https://www.jooq.org/doc/latest/manual/sql-building/dynamic-sql">https://www.jooq.org/doc/latest/manual/sql-building/dynamic-sql</a>.
+ * <p>
+ * Drawbacks of referencing the <code>XYZ*Step</code> types directly:
+ * <ul>
+ * <li>They're operating on mutable implementations (as of jOOQ 3.x)</li>
+ * <li>They're less composable and not easy to get right when dynamic SQL gets
+ * complex</li>
+ * <li>They're less readable</li>
+ * <li>They might have binary incompatible changes between minor releases</li>
+ * </ul>
+ *
+ * @author Lukas Eder
+ */
+public interface MergeMatchedThenStep<R extends Record> {
+
+    /**
+     * Add the <code>WHEN MATCHED THEN UPDATE</code> clause to the
+     * <code>MERGE</code> statement.
+     */
+    @Support({ DERBY, H2, HSQLDB })
+    MergeMatchedSetStep<R> thenUpdate();
+}
diff --git a/jOOQ/src/main/java/org/jooq/impl/ParserImpl.java b/jOOQ/src/main/java/org/jooq/impl/ParserImpl.java
index a2ea33cc3f..69ec3c4d7a 100644
--- a/jOOQ/src/main/java/org/jooq/impl/ParserImpl.java
+++ b/jOOQ/src/main/java/org/jooq/impl/ParserImpl.java
@@ -457,7 +457,6 @@ import org.jooq.LikeEscapeStep;
 import org.jooq.Merge;
 import org.jooq.MergeFinalStep;
 import org.jooq.MergeMatchedStep;
-import org.jooq.MergeNotMatchedStep;
 import org.jooq.MergeUsingStep;
 import org.jooq.Meta;
 import org.jooq.Name;
@@ -2047,18 +2046,30 @@ final class ParserImpl implements Parser {
         List<Field<?>> insertValues = null;
         Condition insertWhere = null;
         Map<Field<?>, Object> updateSet = null;
+        Condition updateAnd = null;
         Condition updateWhere = null;
 
+        MergeUsingStep<?> s1 = (with == null ? ctx.dsl.mergeInto(target) : with.mergeInto(target));
+        MergeMatchedStep<?> s2 = s1.using(usingTable).on(on);
+
         for (;;) {
-            if (!update && (update = parseKeywordIf(ctx, "WHEN MATCHED"))) {
+            if (parseKeywordIf(ctx, "WHEN MATCHED")) {
+                update = true;
+
                 if (parseKeywordIf(ctx, "AND"))
-                    updateWhere = parseCondition(ctx);
+                    updateAnd = parseCondition(ctx);
 
                 parseKeyword(ctx, "THEN UPDATE SET");
                 updateSet = parseSetClauseList(ctx);
 
-                if (updateWhere == null && parseKeywordIf(ctx, "WHERE"))
+                if (updateAnd == null && parseKeywordIf(ctx, "WHERE"))
                     updateWhere = parseCondition(ctx);
+
+                s2 = updateAnd != null
+                   ? s2.whenMatchedAnd(updateAnd).thenUpdate().set(updateSet)
+                   : updateWhere != null
+                   ? s2.whenMatchedThenUpdate().set(updateSet).where(updateWhere)
+                   : s2.whenMatchedThenUpdate().set(updateSet);
             }
             else if (!insert && (insert = parseKeywordIf(ctx, "WHEN NOT MATCHED"))) {
                 if (parseKeywordIf(ctx, "AND"))
@@ -2093,21 +2104,13 @@ final class ParserImpl implements Parser {
 
         // TODO support multi clause MERGE
         // TODO support DELETE
-
-        MergeUsingStep<?> s1 = (with == null ? ctx.dsl.mergeInto(target) : with.mergeInto(target));
-        MergeMatchedStep<?> s2 = s1.using(usingTable).on(on);
-        MergeNotMatchedStep<?> s3 = update
-            ? updateWhere != null
-                ? s2.whenMatchedThenUpdate().set(updateSet).where(updateWhere)
-                : s2.whenMatchedThenUpdate().set(updateSet)
-            : s2;
-        MergeFinalStep<?> s4 = insert
+        MergeFinalStep<?> s3 = insert
             ? insertWhere != null
-                ? s3.whenNotMatchedThenInsert(insertColumns).values(insertValues).where(insertWhere)
-                : s3.whenNotMatchedThenInsert(insertColumns).values(insertValues)
-            : s3;
+                ? s2.whenNotMatchedThenInsert(insertColumns).values(insertValues).where(insertWhere)
+                : s2.whenNotMatchedThenInsert(insertColumns).values(insertValues)
+            : s2;
 
-        return s4;
+        return s3;
     }
 
     private static final Query parseSet(ParserContext ctx) {