diff --git a/CHANGELOG.md b/CHANGELOG.md
index c64b20a4..f0e1dcea 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -7,6 +7,12 @@ and this project adheres to [Semantic Versioning](https://semver.org/spec/v2.0.0
 
 ## [1.0.1] - 2020-05-08
 
+### Fixed
+
+- Issue with Windows legacy support https://github.com/willmcgugan/rich/issues/59
+
+## [1.0.1] - 2020-05-08
+
 ### Changed
 
 - Applied console markup after highlighting
diff --git a/pyproject.toml b/pyproject.toml
index a74bc9cd..3099f743 100644
--- a/pyproject.toml
+++ b/pyproject.toml
@@ -2,7 +2,7 @@
 name = "rich"
 homepage = "https://github.com/willmcgugan/rich"
 documentation = "https://rich.readthedocs.io/en/latest/"
-version = "1.0.1"
+version = "1.0.2"
 description = "Render rich text, tables, progress bars, syntax highlighting, markdown and more to the terminal"
 authors = ["Will McGugan <willmcgugan@gmail.com>"]
 license = "MIT"
diff --git a/rich/console.py b/rich/console.py
index ff9ee66c..d3e1b548 100644
--- a/rich/console.py
+++ b/rich/console.py
@@ -210,8 +210,12 @@ class ConsoleThreadLocals(threading.local):
     control: List[str] = field(default_factory=list)
 
 
-def _enable_legacy_windows_support() -> None:
-    """Initialize Windows legacy support."""
+def detect_legacy_windows() -> bool:
+    """Detect legacy Windows."""
+    return "WINDIR" in os.environ and "WT_SESSION" not in os.environ
+
+
+if detect_legacy_windows():
     from colorama import init
 
     init()
@@ -266,12 +270,11 @@ class Console:
         self._markup = markup
         self._emoji = emoji
         self._highlight = highlight
-        self.legacy_windows: bool = "WINDIR" in os.environ and not "WT_SESSION" in os.environ
+        self.legacy_windows: bool = detect_legacy_windows()
 
         self._color_system: Optional[ColorSystem]
         self._force_terminal = force_terminal
         if self.legacy_windows:
-            _enable_legacy_windows_support()
             self.file = file or sys.stdout
             self._color_system = COLOR_SYSTEMS["windows"]
         else: