diff --git a/jOOQ/src/main/java/org/jooq/impl/AbstractRow.java b/jOOQ/src/main/java/org/jooq/impl/AbstractRow.java
index 935184054f..d4ce30d43d 100644
--- a/jOOQ/src/main/java/org/jooq/impl/AbstractRow.java
+++ b/jOOQ/src/main/java/org/jooq/impl/AbstractRow.java
@@ -45,6 +45,7 @@ import static org.jooq.impl.Names.N_ROW;
 import static org.jooq.impl.QueryPartListView.wrap;
 import static org.jooq.impl.Tools.extractVal;
 import static org.jooq.impl.Tools.isVal;
+import static org.jooq.impl.Tools.isVal1;
 import static org.jooq.impl.Tools.nullSafe;
 
 import java.util.Collection;
@@ -224,7 +225,8 @@ implements
 
         findConversionCandidates: {
             for (int i = 0; i < size; i++)
-                if (isVal(fields.field(i)) && !isVal(row.field(i)))
+                if (isVal1(fields.field(i), v -> v.inferredDataType)
+                    && !isVal1(row.field(i), v -> v.inferredDataType))
                     break findConversionCandidates;
 
             return this;
@@ -233,10 +235,12 @@ implements
         Field<?>[] result = new Field[size];
         for (int i = 0; i < size; i++) {
             Field<?> f = fields.field(i);
-            Val<?> v;
+            Val<?> val;
 
-            if ((v = extractVal(f)) != null)
-                result[i] = v.convertTo(row.field(i).getDataType());
+            if (isVal1(fields.field(i), v -> v.inferredDataType)
+                    && !isVal1(row.field(i), v -> v.inferredDataType)
+                    && (val = extractVal(f)) != null)
+                result[i] = val.convertTo(row.field(i).getDataType());
             else
                 result[i] = f;
         }
diff --git a/jOOQ/src/main/java/org/jooq/impl/DefaultDataType.java b/jOOQ/src/main/java/org/jooq/impl/DefaultDataType.java
index dd18e5c989..3ac2d66f19 100644
--- a/jOOQ/src/main/java/org/jooq/impl/DefaultDataType.java
+++ b/jOOQ/src/main/java/org/jooq/impl/DefaultDataType.java
@@ -843,14 +843,34 @@ public class DefaultDataType<T> extends AbstractDataTypeX<T> {
     private static final class DiscouragedStaticTypeRegistryUsage extends RuntimeException {}
 
     public static final <T> DataType<T> getDataType(SQLDialect dialect, Class<T> type, DataType<T> fallbackDataType) {
-        return check(getDataType0(dialect, type, fallbackDataType));
+        return getDataType0(dialect, type, fallbackDataType);
     }
 
-    private static final <T> DataType<T> check(DataType<T> result) {
+    static final <T> DataType<T> check(DataType<T> result) {
 
         // [#5713] [#15286] TODO: Move this to a dynamic type registry and make warning configurable
-        if (result instanceof ConvertedDataType || result instanceof LegacyConvertedDataType)
-            getDataType.warn("Static type registry", "The deprecated static type registry was being accessed for a non-built-in data type: " + result + ". It is strongly recommended not looking up DataType<T> references from Class<T> references by relying on the internal static type registry. See https://github.com/jOOQ/jOOQ/issues/15286 for details.", new DiscouragedStaticTypeRegistryUsage());
+        if (result instanceof LegacyConvertedDataType) {
+            DiscouragedStaticTypeRegistryUsage e = new DiscouragedStaticTypeRegistryUsage();
+
+            getDataType.warn("Static type registry", """
+                The deprecated static type registry was being accessed for a non-built-in data type: {result}.
+
+                It is strongly recommended not looking up DataType<T> references from Class<T> references by
+                relying on the internal static type registry. For example, avoid calling DSL.val(Object) or
+                DSL.val(Object, Class), and call DSL.val(Object, DataType), providing an explicit DataType
+                reference to jOOQ if your DataType uses a Converter or a Binding. If you think jOOQ should
+                be able to infer your user type in your particular query, please report a bug here:
+                https://jooq.org/bug
+
+                See https://github.com/jOOQ/jOOQ/issues/15286 for more details.
+                """.replace("{result}", "" + result), e);
+
+            // [#16090] [#16425]
+            // An undocumented flag to throw the logged exception to help with faster fixing of this problem
+            // Users should not rely on this flag as it may be removed without announcement when it isn't needed anymore.
+            if ("true".equals(System.getProperty("org.jooq.throw-on-discouraged-static-type-registry-access")))
+                throw e;
+        }
 
         if (result instanceof ArrayDataType<?> a)
             check(a.elementType);
diff --git a/jOOQ/src/main/java/org/jooq/impl/Val.java b/jOOQ/src/main/java/org/jooq/impl/Val.java
index e0ce74568c..027b538d9e 100644
--- a/jOOQ/src/main/java/org/jooq/impl/Val.java
+++ b/jOOQ/src/main/java/org/jooq/impl/Val.java
@@ -177,6 +177,11 @@ final class Val<T> extends AbstractParam<T> implements UEmpty {
 
     @Override
     public void accept(Context<?> ctx) {
+    	
+    	// [#16090] [#16425] Inferred user types shouldn't rely on static type registry
+        if (inferredDataType)
+            DefaultDataType.check(getDataType());
+
         if (getDataType().isEmbeddable()) {
 
             // TODO [#12021] [#12706] ROW must consistently follow MULTISET emulation