diff --git a/lua/nvim-tree/utils.lua b/lua/nvim-tree/utils.lua
index 936982ec0a7..194845f5c1f 100644
--- a/lua/nvim-tree/utils.lua
+++ b/lua/nvim-tree/utils.lua
@@ -70,6 +70,23 @@ local function has_parentheses_and_brackets(path)
   return false
 end
 
+--- Path normalizations for windows only
+local function win_norm_path(path)
+  if path == nil then
+    return path
+  end
+  local norm_path = path
+  -- Normalize for issue #2862 and #2961
+  if has_parentheses_and_brackets(norm_path) then
+    norm_path = norm_path:gsub("/", "\\")
+  end
+  -- Normalize the drive letter
+  norm_path = norm_path:gsub("^%l:", function(drive)
+    return drive:upper()
+  end)
+  return norm_path
+end
+
 --- Get a path relative to another path.
 ---@param path string
 ---@param relative_to string|nil
@@ -80,8 +97,8 @@ function M.path_relative(path, relative_to)
   end
 
   local norm_path = path
-  if M.is_windows and has_parentheses_and_brackets(path) then
-    norm_path = path:gsub("/", "\\")
+  if M.is_windows then
+    norm_path = win_norm_path(norm_path)
   end
 
   local _, r = norm_path:find(M.path_add_trailing(relative_to), 1, true)