diff --git a/packages/prettier-plugin-java/src/printers/helpers.ts b/packages/prettier-plugin-java/src/printers/helpers.ts
index 8677cb152..bf0ec40c7 100644
--- a/packages/prettier-plugin-java/src/printers/helpers.ts
+++ b/packages/prettier-plugin-java/src/printers/helpers.ts
@@ -304,26 +304,30 @@ export function printClassType(
   path: AstPath<JavaNonTerminal & { children: ClassTypeCtx }>,
   print: JavaPrintFn
 ) {
-  return flatMap(
-    path,
-    childPath => {
-      const { node, isLast } = childPath;
-      const child = [print(childPath)];
-      if (isTerminal(node)) {
-        if (!isLast) {
-          child.push(".");
+  const { children } = path.node;
+  return definedKeys(children, ["annotation", "Identifier", "typeArguments"])
+    .flatMap(child =>
+      children[child]!.map((node, index) => ({
+        child,
+        index,
+        startOffset: parser.locStart(node)
+      }))
+    )
+    .sort((a, b) => a.startOffset - b.startOffset)
+    .flatMap(({ child, index: childIndex }, index, array) => {
+      const node = children[child]![childIndex];
+      const next = array.at(index + 1);
+      const nextNode = next && children[next.child]![next.index];
+      const docs = [call(path, print, child, childIndex)];
+      if (nextNode) {
+        if (isNonTerminal(node)) {
+          docs.push(node.name === "annotation" ? " " : ".");
+        } else if (isTerminal(nextNode) || nextNode.name === "annotation") {
+          docs.push(".");
         }
-      } else if (node.name === "annotation") {
-        child.push(" ");
       }
-      return child;
-    },
-    definedKeys(path.node.children, [
-      "annotation",
-      "Identifier",
-      "typeArguments"
-    ])
-  );
+      return docs;
+    });
 }
 
 export function isBinaryExpression(expression: ExpressionCstNode) {
diff --git a/packages/prettier-plugin-java/test/unit-test/types/_input.java b/packages/prettier-plugin-java/test/unit-test/types/_input.java
index 213d4b9f2..7163ef0ef 100644
--- a/packages/prettier-plugin-java/test/unit-test/types/_input.java
+++ b/packages/prettier-plugin-java/test/unit-test/types/_input.java
@@ -23,4 +23,8 @@ public void dataTypes() {
     String stringVariable;
   }
 
+  public void complexTypes() {
+    @A B.C<D>.@E @F G.H h;
+  }
+
 }
diff --git a/packages/prettier-plugin-java/test/unit-test/types/_output.java b/packages/prettier-plugin-java/test/unit-test/types/_output.java
index 425f492a4..8052ddedf 100644
--- a/packages/prettier-plugin-java/test/unit-test/types/_output.java
+++ b/packages/prettier-plugin-java/test/unit-test/types/_output.java
@@ -22,4 +22,9 @@ public void dataTypes() {
     Boolean booleanVariable;
     String stringVariable;
   }
+
+  public void complexTypes() {
+    @A
+    B.C<D>.@E @F G.H h;
+  }
 }