diff --git a/CHANGELOG.md b/CHANGELOG.md
index a4447de29..25eb9a908 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -10,6 +10,7 @@ and this project adheres to [Semantic Versioning](https://semver.org/spec/v2.0.0
 ### Changed
 
 - Bumped minimum Python version to 3.7 https://github.com/Textualize/rich/pull/2567
+- Pretty-printing of "tagged" `__repr__` results is now greedy when matching tags https://github.com/Textualize/rich/pull/2565
 
 ## [12.6.0] - 2022-10-02
 
diff --git a/tests/test_highlighter.py b/tests/test_highlighter.py
index a9d036ba9..804efb369 100644
--- a/tests/test_highlighter.py
+++ b/tests/test_highlighter.py
@@ -5,10 +5,10 @@
 import pytest
 
 from rich.highlighter import (
+    ISO8601Highlighter,
     JSONHighlighter,
     NullHighlighter,
     ReprHighlighter,
-    ISO8601Highlighter,
 )
 from rich.text import Span, Text
 
@@ -30,6 +30,26 @@ def test_wrong_type():
             Span(4, 5, "repr.tag_end"),
         ],
     ),
+    (
+        "<foo: 23>",
+        [
+            Span(0, 1, "repr.tag_start"),
+            Span(1, 5, "repr.tag_name"),
+            Span(5, 8, "repr.tag_contents"),
+            Span(8, 9, "repr.tag_end"),
+            Span(6, 8, "repr.number"),
+        ],
+    ),
+    (
+        "<foo: <bar: 23>>",
+        [
+            Span(0, 1, "repr.tag_start"),
+            Span(1, 5, "repr.tag_name"),
+            Span(5, 15, "repr.tag_contents"),
+            Span(15, 16, "repr.tag_end"),
+            Span(12, 14, "repr.number"),
+        ],
+    ),
     (
         "False True None",
         [