diff --git a/pkg/styles/theme.go b/pkg/styles/theme.go
index 504db7475fd..8a4be34d989 100644
--- a/pkg/styles/theme.go
+++ b/pkg/styles/theme.go
@@ -48,6 +48,7 @@ package styles
 
 import (
 	"os"
+	"runtime"
 
 	lipgloss "charm.land/lipgloss/v2"
 	"charm.land/lipgloss/v2/compat"
@@ -59,8 +60,36 @@ func configureLipglossCompat() {
 	compat.Profile = colorprofile.Detect(os.Stderr, os.Environ())
 }
 
+func shouldConfigureLipglossCompat(goos string, stderrMode os.FileMode, statErr error) bool {
+	// On Windows, querying terminal capabilities against redirected/pipe handles
+	// can hang under some wrapper environments. Skip startup probing unless stderr
+	// is attached to a character device.
+	if goos == "windows" {
+		if statErr != nil {
+			return false
+		}
+		return stderrMode&(os.ModeDevice|os.ModeCharDevice) == (os.ModeDevice | os.ModeCharDevice)
+	}
+	return true
+}
+
 func init() {
-	configureLipglossCompat()
+	stderrInfo, statErr := os.Stderr.Stat()
+	// Defensive fallback: Stat should not normally return (nil, nil). Treat that
+	// impossible state as an invalid stderr handle so Windows startup probing is
+	// safely skipped.
+	if statErr == nil && stderrInfo == nil {
+		statErr = os.ErrInvalid
+	}
+	// Zero mode means "unknown/unset"; on Windows this keeps the startup probe
+	// disabled unless stderr is explicitly confirmed as a character device.
+	stderrMode := os.FileMode(0)
+	if stderrInfo != nil {
+		stderrMode = stderrInfo.Mode()
+	}
+	if shouldConfigureLipglossCompat(runtime.GOOS, stderrMode, statErr) {
+		configureLipglossCompat()
+	}
 }
 
 // Hex color constants for light and dark variants.
diff --git a/pkg/styles/theme_test.go b/pkg/styles/theme_test.go
index d797cb6e8a2..583d0d09a36 100644
--- a/pkg/styles/theme_test.go
+++ b/pkg/styles/theme_test.go
@@ -280,6 +280,63 @@ func TestConfigureLipglossCompatUsesStderr(t *testing.T) {
 	}
 }
 
+func TestShouldConfigureLipglossCompat(t *testing.T) {
+	tests := []struct {
+		name       string
+		goos       string
+		stderrMode os.FileMode
+		statErr    error
+		want       bool
+	}{
+		{
+			name:       "windows character device",
+			goos:       "windows",
+			stderrMode: os.ModeDevice | os.ModeCharDevice,
+			want:       true,
+		},
+		{
+			name:       "windows redirected pipe",
+			goos:       "windows",
+			stderrMode: os.ModeNamedPipe,
+			want:       false,
+		},
+		{
+			name:       "windows zero mode stat success",
+			goos:       "windows",
+			stderrMode: os.FileMode(0),
+			want:       false,
+		},
+		{
+			name:    "windows stat error",
+			goos:    "windows",
+			statErr: os.ErrPermission,
+			want:    false,
+		},
+		{
+			name:    "windows ErrInvalid fallback",
+			goos:    "windows",
+			statErr: os.ErrInvalid,
+			want:    false,
+		},
+		{
+			name:       "non-windows still configures",
+			goos:       "linux",
+			stderrMode: os.ModeNamedPipe,
+			statErr:    os.ErrPermission,
+			want:       true,
+		},
+	}
+
+	for _, tt := range tests {
+		t.Run(tt.name, func(t *testing.T) {
+			got := shouldConfigureLipglossCompat(tt.goos, tt.stderrMode, tt.statErr)
+			if got != tt.want {
+				t.Fatalf("shouldConfigureLipglossCompat(%q, %v, %v) = %v, want %v", tt.goos, tt.stderrMode, tt.statErr, got, tt.want)
+			}
+		})
+	}
+}
+
 // TestBordersExist verifies that all expected border definitions are defined
 func TestBordersExist(t *testing.T) {
 	borders := map[string]lipgloss.Border{