diff --git a/CHANGELOG.md b/CHANGELOG.md
index 8191a7767..c86bf324c 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -16,6 +16,7 @@ and this project adheres to [Semantic Versioning](https://semver.org/spec/v2.0.0
 ### Fixed
 
 - Fixed issue with Segment._split_cells https://github.com/Textualize/rich/pull/3506
+- Fix auto detection of terminal size on Windows https://github.com/Textualize/rich/pull/2916
 
 ### Added
 
diff --git a/CONTRIBUTORS.md b/CONTRIBUTORS.md
index 9294136fa..4dd14dde1 100644
--- a/CONTRIBUTORS.md
+++ b/CONTRIBUTORS.md
@@ -87,5 +87,6 @@ The following people have contributed to the development of Rich:
 - [Pierro](https://github.com/xpierroz)
 - [Bernhard Wagner](https://github.com/bwagner)
 - [Aaron Beaudoin](https://github.com/AaronBeaudoin)
+- [L. Yeung](https://github.com/lewis-yeung)
 - [chthollyphile](https://github.com/chthollyphile)
 - [Jonathan Helmus](https://github.com/jjhelmus)
diff --git a/rich/console.py b/rich/console.py
index 9e697327b..9ef0d60bb 100644
--- a/rich/console.py
+++ b/rich/console.py
@@ -1005,19 +1005,13 @@ def size(self) -> ConsoleDimensions:
         width: Optional[int] = None
         height: Optional[int] = None
 
-        if WINDOWS:  # pragma: no cover
+        for file_descriptor in _STD_STREAMS_OUTPUT if WINDOWS else _STD_STREAMS:
             try:
-                width, height = os.get_terminal_size()
+                width, height = os.get_terminal_size(file_descriptor)
             except (AttributeError, ValueError, OSError):  # Probably not a terminal
                 pass
-        else:
-            for file_descriptor in _STD_STREAMS:
-                try:
-                    width, height = os.get_terminal_size(file_descriptor)
-                except (AttributeError, ValueError, OSError):
-                    pass
-                else:
-                    break
+            else:
+                break
 
         columns = self._environ.get("COLUMNS")
         if columns is not None and columns.isdigit():