diff --git a/jOOQ/src/main/java/org/jooq/impl/ParserImpl.java b/jOOQ/src/main/java/org/jooq/impl/ParserImpl.java
index 05d14f547f..5983f4add1 100644
--- a/jOOQ/src/main/java/org/jooq/impl/ParserImpl.java
+++ b/jOOQ/src/main/java/org/jooq/impl/ParserImpl.java
@@ -11860,7 +11860,7 @@ final class DefaultParseContext extends AbstractScope implements ParseContext {
         return null;
     }
 
-    private final Field<Boolean> parseBooleanValueExpressionIf() {
+    private final Field<?> parseBooleanValueExpressionIf() {
         TruthValue truth = parseTruthValueIf();
 
         if (truth != null) {
@@ -11869,8 +11869,10 @@ final class DefaultParseContext extends AbstractScope implements ParseContext {
                     return inline(true);
                 case T_FALSE:
                     return inline(false);
+
+                // [#16368] We cannot decide the data type at this point
                 case T_NULL:
-                    return inline((Boolean) null);
+                    return inline(null, OTHER);
                 default:
                     throw exception("Truth value not supported: " + truth);
             }
diff --git a/jOOQ/src/main/java/org/jooq/impl/Patterns.java b/jOOQ/src/main/java/org/jooq/impl/Patterns.java
index c489fb7801..a89f3f59c2 100644
--- a/jOOQ/src/main/java/org/jooq/impl/Patterns.java
+++ b/jOOQ/src/main/java/org/jooq/impl/Patterns.java
@@ -2692,24 +2692,6 @@ package org.jooq.impl;
 
 
 
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
 
 
 
diff --git a/jOOQ/src/main/java/org/jooq/impl/Tools.java b/jOOQ/src/main/java/org/jooq/impl/Tools.java
index 0bdc59bf34..60f80f6eb4 100644
--- a/jOOQ/src/main/java/org/jooq/impl/Tools.java
+++ b/jOOQ/src/main/java/org/jooq/impl/Tools.java
@@ -3979,6 +3979,28 @@ final class Tools {
             || field instanceof ConvertedVal && ((ConvertedVal<?>) field).delegate instanceof Val;
     }
 
+    static final boolean isVal(QueryPart p, Predicate<? super Val<?>> predicate) {
+        if (p instanceof Val<?> v) {
+            return predicate.test(v);
+        }
+        else if (p instanceof ConvertedVal<?> v) {
+            return isVal(v.delegate, predicate);
+        }
+        else
+            return false;
+    }
+
+    static final <T> boolean isVal0(Field<T> p, Predicate<? super Val<T>> predicate) {
+        if (p instanceof Val<T> v) {
+            return predicate.test(v);
+        }
+        else if (p instanceof ConvertedVal<T> v) {
+            return isVal0((Field<T>) v.delegate, predicate);
+        }
+        else
+            return false;
+    }
+
     static final boolean isWindow(QueryPart part) {
         return part instanceof AbstractWindowFunction && ((AbstractWindowFunction<?>) part).isWindow();
     }