diff --git a/CHANGELOG.md b/CHANGELOG.md
index 2df2b1993d..8c86abcb13 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -14,6 +14,7 @@ and this project adheres to [Semantic Versioning](http://semver.org/).
 - Tooltips are now cleared when the related widget is no longer under them https://github.com/Textualize/textual/issues/3045
 - Simplified tree-sitter highlight queries for HTML, which also seems to fix segfault issue https://github.com/Textualize/textual/pull/4195
 - Fixed `DirectoryTree.path` no longer reacting to new values https://github.com/Textualize/textual/issues/4208
+- Fixed content size cache with Pretty widget https://github.com/Textualize/textual/pull/4211
 
 ## [0.52.1] - 2024-02-20
 
diff --git a/src/textual/widget.py b/src/textual/widget.py
index 157e0cb930..665e50ab01 100644
--- a/src/textual/widget.py
+++ b/src/textual/widget.py
@@ -577,6 +577,19 @@ def __exit__(
         else:
             self.app._composed[-1].append(composed)
 
+    def clear_cached_dimensions(self) -> None:
+        """Clear cached results of `get_content_width` and `get_content_height`.
+
+        Call if the widget's renderable changes size after the widget has been created.
+
+        !!! note
+
+            This is not required if you are extending [`Static`][textual.widgets.Static].
+
+        """
+        self._content_width_cache = (None, 0)
+        self._content_height_cache = (None, 0)
+
     def get_loading_widget(self) -> Widget:
         """Get a widget to display a loading indicator.
 
@@ -3278,8 +3291,7 @@ def refresh(
 
         if repaint:
             self._set_dirty(*regions)
-            self._content_width_cache = (None, 0)
-            self._content_height_cache = (None, 0)
+            self.clear_cached_dimensions()
             self._rich_style_cache.clear()
             self._repaint_required = True
 
diff --git a/src/textual/widgets/_pretty.py b/src/textual/widgets/_pretty.py
index 34d88b3964..ffa89819d8 100644
--- a/src/textual/widgets/_pretty.py
+++ b/src/textual/widgets/_pretty.py
@@ -59,4 +59,5 @@ def update(self, object: Any) -> None:
             object: The object to pretty-print.
         """
         self._renderable = PrettyRenderable(object)
+        self.clear_cached_dimensions()
         self.refresh(layout=True)
diff --git a/src/textual/widgets/_static.py b/src/textual/widgets/_static.py
index a9f485345b..3ccd43c3df 100644
--- a/src/textual/widgets/_static.py
+++ b/src/textual/widgets/_static.py
@@ -78,6 +78,7 @@ def renderable(self, renderable: RenderableType) -> None:
                 self._renderable = Text(renderable)
         else:
             self._renderable = renderable
+        self.clear_cached_dimensions()
 
     def render(self) -> RenderableType:
         """Get a rich renderable for the widget's content.