diff --git a/compiler/src/dotty/tools/dotc/reporting/ErrorMessageID.scala b/compiler/src/dotty/tools/dotc/reporting/ErrorMessageID.scala
index e3613e3f783a..cb5e8a7b314c 100644
--- a/compiler/src/dotty/tools/dotc/reporting/ErrorMessageID.scala
+++ b/compiler/src/dotty/tools/dotc/reporting/ErrorMessageID.scala
@@ -214,6 +214,7 @@ enum ErrorMessageID(val isActive: Boolean = true) extends java.lang.Enum[ErrorMe
   case UnusedSymbolID // errorNumber: 198
   case TailrecNestedCallID //errorNumber: 199
   case FinalLocalDefID // errorNumber: 200
+  case NonNamedArgumentInJavaAnnotationID // errorNumber: 201
 
   def errorNumber = ordinal - 1
 
diff --git a/compiler/src/dotty/tools/dotc/reporting/messages.scala b/compiler/src/dotty/tools/dotc/reporting/messages.scala
index 1d906130d4e4..f112b6fb5aa7 100644
--- a/compiler/src/dotty/tools/dotc/reporting/messages.scala
+++ b/compiler/src/dotty/tools/dotc/reporting/messages.scala
@@ -3288,3 +3288,25 @@ object UnusedSymbol {
     def privateMembers(using Context): UnusedSymbol = new UnusedSymbol(i"unused private member")
     def patVars(using Context): UnusedSymbol = new UnusedSymbol(i"unused pattern variable")
 }
+
+class NonNamedArgumentInJavaAnnotation(using Context) extends SyntaxMsg(NonNamedArgumentInJavaAnnotationID):
+
+  override protected def msg(using Context): String = 
+    "Named arguments are required for Java defined annotations"
+
+  override protected def explain(using Context): String = 
+    i"""Starting from Scala 3.6.0, named arguments are required for Java defined annotations.
+        |Java defined annotations don't have an exact constructor representation 
+        |and we previously relied on the order of the fields to create one. 
+        |One possible issue with this representation is the reordering of the fields.
+        |Lets take the following example:
+        |
+        |  public @interface Annotation {
+        |    int a() default 41;
+        |    int b() default 42;
+        |  }
+        |
+        |Reordering the fields is binary-compatible but it might affect the meaning of @Annotation(1)
+        """
+
+end NonNamedArgumentInJavaAnnotation
diff --git a/compiler/src/dotty/tools/dotc/typer/Checking.scala b/compiler/src/dotty/tools/dotc/typer/Checking.scala
index 421f00e61584..cbeaf95b91fc 100644
--- a/compiler/src/dotty/tools/dotc/typer/Checking.scala
+++ b/compiler/src/dotty/tools/dotc/typer/Checking.scala
@@ -1527,6 +1527,17 @@ trait Checking {
       // TODO: Add more checks here
     }
 
+  /** check that parameters of a java defined annotations are all named arguments if we have more than one parameter */
+  def checkNamedArgumentForJavaAnnotation(annot: untpd.Tree)(using Context): Unit = 
+    assert(annot.symbol.is(JavaDefined))
+    annot match
+      case untpd.Apply(_, params) if params.length > 1 => 
+        for param <- params
+        if !param.isInstanceOf[untpd.NamedArg]
+        do report.error(NonNamedArgumentInJavaAnnotation(), param)
+      case _ => 
+  end checkNamedArgumentForJavaAnnotation
+
   /** Check that symbol's external name does not clash with symbols defined in the same scope */
   def checkNoTargetNameConflict(stats: List[Tree])(using Context): Unit =
     var seen = Set[Name]()
diff --git a/compiler/src/dotty/tools/dotc/typer/Typer.scala b/compiler/src/dotty/tools/dotc/typer/Typer.scala
index 32f04c13a3d6..dea675cef71c 100644
--- a/compiler/src/dotty/tools/dotc/typer/Typer.scala
+++ b/compiler/src/dotty/tools/dotc/typer/Typer.scala
@@ -2737,6 +2737,8 @@ class Typer(@constructorOnly nestingLevel: Int = 0) extends Namer
     lazy val annotCtx = annotContext(mdef, sym)
     // necessary in order to mark the typed ahead annotations as definitely typed:
     for (annot <- mdef.mods.annotations)
+      if (annot.symbol.is(JavaDefined)) then
+        checkNamedArgumentForJavaAnnotation(annot)
       val annot1 = typedAnnotation(annot)(using annotCtx)
       checkAnnotApplicable(annot1, sym)
       if Annotations.annotClass(annot1) == defn.NowarnAnnot then
diff --git a/tests/neg/i20554.check b/tests/neg/i20554.check
new file mode 100644
index 000000000000..4faa4da6fd09
--- /dev/null
+++ b/tests/neg/i20554.check
@@ -0,0 +1,42 @@
+-- [E201] Syntax Error: tests/neg/i20554/Test.scala:3:12 ---------------------------------------------------------------
+3 |@Annotation(3, 4) // error // error
+  |            ^
+  |            Named arguments are required for Java defined annotations
+  |---------------------------------------------------------------------------------------------------------------------
+  | Explanation (enabled by `-explain`)
+  |- - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - -
+  | Starting from Scala 3.6.0, named arguments are required for Java defined annotations.
+  | Java defined annotations don't have an exact constructor representation 
+  | and we previously relied on the order of the fields to create one. 
+  | One possible issue with this representation is the reordering of the fields.
+  | Lets take the following example:
+  |
+  |   public @interface Annotation {
+  |     int a() default 41;
+  |     int b() default 42;
+  |   }
+  |
+  | Reordering the fields is binary-compatible but it might affect the meaning of @Annotation(1)
+  |         
+   ---------------------------------------------------------------------------------------------------------------------
+-- [E201] Syntax Error: tests/neg/i20554/Test.scala:3:15 ---------------------------------------------------------------
+3 |@Annotation(3, 4) // error // error
+  |               ^
+  |               Named arguments are required for Java defined annotations
+  |---------------------------------------------------------------------------------------------------------------------
+  | Explanation (enabled by `-explain`)
+  |- - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - -
+  | Starting from Scala 3.6.0, named arguments are required for Java defined annotations.
+  | Java defined annotations don't have an exact constructor representation 
+  | and we previously relied on the order of the fields to create one. 
+  | One possible issue with this representation is the reordering of the fields.
+  | Lets take the following example:
+  |
+  |   public @interface Annotation {
+  |     int a() default 41;
+  |     int b() default 42;
+  |   }
+  |
+  | Reordering the fields is binary-compatible but it might affect the meaning of @Annotation(1)
+  |         
+   ---------------------------------------------------------------------------------------------------------------------
diff --git a/tests/neg/i20554/Annotation.java b/tests/neg/i20554/Annotation.java
new file mode 100644
index 000000000000..3f8389517eae
--- /dev/null
+++ b/tests/neg/i20554/Annotation.java
@@ -0,0 +1,5 @@
+public @interface Annotation {
+    int a() default 41;
+    int b() default 42;
+    int c() default 43;
+}
diff --git a/tests/neg/i20554/Test.scala b/tests/neg/i20554/Test.scala
new file mode 100644
index 000000000000..ee4adc2bbbea
--- /dev/null
+++ b/tests/neg/i20554/Test.scala
@@ -0,0 +1,4 @@
+//> using options -explain
+
+@Annotation(3, 4) // error // error
+class Test
\ No newline at end of file
diff --git a/tests/pos/i20554/Annotation.java b/tests/pos/i20554/Annotation.java
new file mode 100644
index 000000000000..3f8389517eae
--- /dev/null
+++ b/tests/pos/i20554/Annotation.java
@@ -0,0 +1,5 @@
+public @interface Annotation {
+    int a() default 41;
+    int b() default 42;
+    int c() default 43;
+}
diff --git a/tests/pos/i20554/Container.java b/tests/pos/i20554/Container.java
new file mode 100644
index 000000000000..047363d52bac
--- /dev/null
+++ b/tests/pos/i20554/Container.java
@@ -0,0 +1,3 @@
+public @interface Container {
+    SimpleAnnotation[] value();
+}
diff --git a/tests/pos/i20554/SimpleAnnotation.java b/tests/pos/i20554/SimpleAnnotation.java
new file mode 100644
index 000000000000..33c114c2dfad
--- /dev/null
+++ b/tests/pos/i20554/SimpleAnnotation.java
@@ -0,0 +1,6 @@
+import java.lang.annotation.Repeatable;
+
+@Repeatable(Container.class)
+public @interface SimpleAnnotation {
+    int a() default 1;
+}
diff --git a/tests/pos/i20554/Test.scala b/tests/pos/i20554/Test.scala
new file mode 100644
index 000000000000..427700a963c4
--- /dev/null
+++ b/tests/pos/i20554/Test.scala
@@ -0,0 +1,4 @@
+
+@Container(Array(new SimpleAnnotation(), new SimpleAnnotation(1), new SimpleAnnotation(a = 1)))
+@Annotation(a = 1, b = 2)
+class Test
\ No newline at end of file