diff --git a/jOOQ/src/main/java/org/jooq/impl/Tools.java b/jOOQ/src/main/java/org/jooq/impl/Tools.java
index af0ba97f6a..ff5bbdf7a2 100644
--- a/jOOQ/src/main/java/org/jooq/impl/Tools.java
+++ b/jOOQ/src/main/java/org/jooq/impl/Tools.java
@@ -6166,8 +6166,14 @@ final class Tools {
             }
         }
 
+        String typeName = type.getTypeName(ctx.configuration());
+
         // [#5807] These databases cannot use the DataType.getCastTypeName() (which is simply char in this case)
-        if (type.getFromType() == UUID.class && NO_SUPPORT_CAST_TYPE_IN_DDL.contains(ctx.dialect())) {
+        // [#18965] Or, they require a length, but UUID.hasLength() is false
+        if (type.getFromType() == UUID.class && (
+            NO_SUPPORT_CAST_TYPE_IN_DDL.contains(ctx.dialect())
+            || typeName.startsWith("varchar")
+        )) {
             toSQLDDLTypeDeclaration(ctx, VARCHAR(36));
             return;
         }
@@ -6182,7 +6188,6 @@ final class Tools {
         }
 
         DataType<?> elementType = type.getArrayBaseDataType();
-        String typeName = type.getTypeName(ctx.configuration());