diff --git a/jOOQ/src/main/java/org/jooq/impl/FieldMapsForInsert.java b/jOOQ/src/main/java/org/jooq/impl/FieldMapsForInsert.java
index bb61ba8b11..f0b7bc9622 100644
--- a/jOOQ/src/main/java/org/jooq/impl/FieldMapsForInsert.java
+++ b/jOOQ/src/main/java/org/jooq/impl/FieldMapsForInsert.java
@@ -103,16 +103,16 @@ import org.jooq.impl.Tools.BooleanDataKey;
  * @author Lukas Eder
  */
 final class FieldMapsForInsert extends AbstractQueryPart implements UNotYetImplemented {
-    private static final Set<SQLDialect> CASTS_NEEDED     = SQLDialect.supportedBy(POSTGRES, YUGABYTEDB);
+    static final Set<SQLDialect>        CASTS_NEEDED = SQLDialect.supportedBy(POSTGRES, YUGABYTEDB);
 
-    final Table<?>                       table;
-    final Map<Field<?>, Field<?>>        empty;
+    final Table<?>                      table;
+    final Map<Field<?>, Field<?>>       empty;
     // Depending on whether embeddable types are allowed, this data structure
     // needs to be flattened with duplicates removed, prior to consumption
     // [#2530] [#6124] [#10481] TODO: Refactor and optimise these flattening algorithms
-    final Map<Field<?>, List<Field<?>>>  values;
-    int                                  rows;
-    int                                  nextRow          = -1;
+    final Map<Field<?>, List<Field<?>>> values;
+    int                                 rows;
+    int                                 nextRow      = -1;
 
     FieldMapsForInsert(Table<?> table) {
         this.table = table;
diff --git a/jOOQ/src/main/java/org/jooq/impl/InsertQueryImpl.java b/jOOQ/src/main/java/org/jooq/impl/InsertQueryImpl.java
index b1ba763927..b762827f99 100644
--- a/jOOQ/src/main/java/org/jooq/impl/InsertQueryImpl.java
+++ b/jOOQ/src/main/java/org/jooq/impl/InsertQueryImpl.java
@@ -59,6 +59,7 @@ import static org.jooq.SQLDialect.MYSQL;
 // ...
 import static org.jooq.SQLDialect.POSTGRES;
 // ...
+// ...
 import static org.jooq.SQLDialect.SQLITE;
 // ...
 // ...
diff --git a/jOOQ/src/main/java/org/jooq/impl/Values.java b/jOOQ/src/main/java/org/jooq/impl/Values.java
index 6e16674146..77707d7c6c 100644
--- a/jOOQ/src/main/java/org/jooq/impl/Values.java
+++ b/jOOQ/src/main/java/org/jooq/impl/Values.java
@@ -53,6 +53,7 @@ import static org.jooq.SQLDialect.MARIADB;
 import static org.jooq.SQLDialect.MYSQL;
 // ...
 // ...
+import static org.jooq.SQLDialect.POSTGRES;
 // ...
 // ...
 // ...
@@ -60,6 +61,7 @@ import static org.jooq.SQLDialect.MYSQL;
 // ...
 import static org.jooq.conf.ParamType.INLINED;
 import static org.jooq.impl.DSL.name;
+import static org.jooq.impl.DSL.row;
 import static org.jooq.impl.Keywords.K_MULTISET;
 import static org.jooq.impl.Keywords.K_ROW;
 import static org.jooq.impl.Keywords.K_STRUCT;
@@ -69,7 +71,9 @@ import static org.jooq.impl.Keywords.K_VALUES;
 import static org.jooq.impl.QueryPartListView.wrap;
 import static org.jooq.impl.SubqueryCharacteristics.DERIVED_TABLE;
 import static org.jooq.impl.Tools.EMPTY_ROW;
+import static org.jooq.impl.Tools.anyMatch;
 import static org.jooq.impl.Tools.isEmpty;
+import static org.jooq.impl.Tools.isVal;
 import static org.jooq.impl.Tools.map;
 import static org.jooq.impl.Tools.visitSubquery;
 
@@ -101,9 +105,10 @@ implements
     QOM.Values<R>
 {
 
-    static final Set<SQLDialect>    NO_SUPPORT_VALUES      = SQLDialect.supportedUntil(FIREBIRD, MARIADB);
-    static final Set<SQLDialect>    REQUIRE_ROWTYPE_CAST   = SQLDialect.supportedBy(FIREBIRD);
-    static final Set<SQLDialect>    NO_SUPPORT_PARENTHESES = SQLDialect.supportedBy();
+    static final Set<SQLDialect>    NO_SUPPORT_VALUES             = SQLDialect.supportedUntil(FIREBIRD, MARIADB);
+    static final Set<SQLDialect>    REQUIRE_ROWTYPE_CAST          = SQLDialect.supportedBy(FIREBIRD);
+    static final Set<SQLDialect>    REQUIRE_ROWTYPE_CAST_ON_NULLS = SQLDialect.supportedBy(POSTGRES);
+    static final Set<SQLDialect>    NO_SUPPORT_PARENTHESES        = SQLDialect.supportedBy();
 
     private final Row[]             rows;
     private transient DataType<?>[] types;
@@ -198,6 +203,27 @@ implements
         return result;
     }
 
+    private final Row castNullLiteralToRowType(Context<?> ctx, Row row) {
+        if (anyMatch(row.fields(), f -> rendersNullLiteral(ctx, f))) {
+            Field<?>[] result = new Field[row.size()];
+
+            for (int i = 0; i < result.length; i++)
+                if (rendersNullLiteral(ctx, row.field(i)) && rowType()[i].getType() != Object.class)
+                    result[i] = row.field(i).cast(rowType()[i]);
+                else
+                    result[i] = row.field(i);
+
+            return row(result);
+        }
+        else
+            return row;
+    }
+
+    private final boolean rendersNullLiteral(Context<?> ctx, Field<?> field) {
+        return isVal(field) && ((Val<?>) field).getValue() == null && ((Val<?>) field).isInline(ctx)
+            || field instanceof NullCondition;
+    }
+
     @Override
     public final void accept(Context<?> ctx) {
 
@@ -266,7 +292,11 @@ implements
 
 
 
-                ctx.visit(rows[i]);
+                // [#11015] NULL literals of known type should be cast in PostgreSQL in the first row
+                if (i == 0 && ctx.family() == POSTGRES)
+                    ctx.visit(castNullLiteralToRowType(ctx, rows[i]));
+                else
+                    ctx.visit(rows[i]);
             }
 
             if (rows.length > 1)