diff --git a/src/modules/poweraccent/PowerAccent.Core/PowerAccent.cs b/src/modules/poweraccent/PowerAccent.Core/PowerAccent.cs
index b7ffcbc8e7..e419bd07b7 100644
--- a/src/modules/poweraccent/PowerAccent.Core/PowerAccent.cs
+++ b/src/modules/poweraccent/PowerAccent.Core/PowerAccent.cs
@@ -62,7 +62,7 @@ public class PowerAccent : IDisposable
     private void ShowToolbar(LetterKey letterKey)
     {
         _visible = true;
-        _characters = WindowsFunctions.IsCapitalState() ? ToUpper(SettingsService.GetDefaultLetterKey(letterKey)) : SettingsService.GetDefaultLetterKey(letterKey);
+        _characters = (WindowsFunctions.IsCapsLockState() || WindowsFunctions.IsShiftState()) ? ToUpper(SettingsService.GetDefaultLetterKey(letterKey)) : SettingsService.GetDefaultLetterKey(letterKey);
         Task.Delay(_settingService.InputTime).ContinueWith(
             t =>
             {
@@ -144,16 +144,27 @@ public class PowerAccent : IDisposable
             }
         }
 
-        if (triggerKey == TriggerKey.Left && _selectedIndex > 0)
+        if (triggerKey == TriggerKey.Left)
         {
             --_selectedIndex;
         }
 
-        if (triggerKey == TriggerKey.Right && _selectedIndex < _characters.Length - 1)
+        if (triggerKey == TriggerKey.Right)
         {
             ++_selectedIndex;
         }
 
+        // Wrap around at beginning and end of _selectedIndex range
+        if (_selectedIndex < 0)
+        {
+            _selectedIndex = _characters.Length - 1;
+        }
+
+        if (_selectedIndex > _characters.Length - 1)
+        {
+            _selectedIndex = 0;
+        }
+
         OnSelectCharacter?.Invoke(_selectedIndex, _characters[_selectedIndex]);
     }
 
diff --git a/src/modules/poweraccent/PowerAccent.Core/Tools/WindowsFunctions.cs b/src/modules/poweraccent/PowerAccent.Core/Tools/WindowsFunctions.cs
index 21f7a44c86..ccecc2ac3e 100644
--- a/src/modules/poweraccent/PowerAccent.Core/Tools/WindowsFunctions.cs
+++ b/src/modules/poweraccent/PowerAccent.Core/Tools/WindowsFunctions.cs
@@ -70,10 +70,15 @@ internal static class WindowsFunctions
         return (monitorInfo.rcWork.Location, monitorInfo.rcWork.Size, dpi);
     }
 
-    public static bool IsCapitalState()
+    public static bool IsCapsLockState()
     {
         var capital = User32.GetKeyState((int)User32.VK.VK_CAPITAL);
+        return capital != 0;
+    }
+
+    public static bool IsShiftState()
+    {
         var shift = User32.GetKeyState((int)User32.VK.VK_SHIFT);
-        return capital != 0 || shift < 0;
+        return shift < 0;
     }
 }