diff --git a/changelogs/fragments/win_copy-empty-dir.yaml b/changelogs/fragments/win_copy-empty-dir.yaml
new file mode 100644
index 0000000000..dbc242d315
--- /dev/null
+++ b/changelogs/fragments/win_copy-empty-dir.yaml
@@ -0,0 +1,2 @@
+bugfixes:
+- win_copy - Fix copy of a dir that contains an empty directory - https://github.com/ansible/ansible/issues/50077
diff --git a/lib/ansible/modules/windows/win_copy.ps1 b/lib/ansible/modules/windows/win_copy.ps1
index 12cfbc9515..50ae1c61aa 100644
--- a/lib/ansible/modules/windows/win_copy.ps1
+++ b/lib/ansible/modules/windows/win_copy.ps1
@@ -127,13 +127,13 @@ Function Copy-Folder($source, $dest) {
 
 Function Get-FileSize($path) {
     $file = Get-Item -Path $path -Force
-    $size = $null
     if ($file.PSIsContainer) {
         $dir_files_sum = Get-ChildItem $file.FullName -Recurse
-        if ($dir_files_sum -eq $null -or ($dir_files_sum.PSObject.Properties.name -contains 'length' -eq $false)) {
+        $size = (Get-ChildItem -Path $file.FullName -Recurse -Force | `
+            Where-Object { $_.PSObject.Properties.Name -contains 'Length' } | `
+            Measure-Object -Property Length -Sum).Sum
+        if ($null -eq $size) {
             $size = 0
-        } else {
-            $size = ($dir_files_sum | Measure-Object -property length -sum).Sum
         }
     } else {
         $size = $file.Length
diff --git a/test/integration/targets/win_copy/tasks/remote_tests.yml b/test/integration/targets/win_copy/tasks/remote_tests.yml
index cdbf2c5dba..0a8d41e26c 100644
--- a/test/integration/targets/win_copy/tasks/remote_tests.yml
+++ b/test/integration/targets/win_copy/tasks/remote_tests.yml
@@ -412,3 +412,60 @@
     - remote_copy_folder_content_to_folder_after_change_actual.matched == 2
     - remote_copy_folder_content_to_folder_after_change_actual.files[0].checksum == 'b54ba7f5621240d403f06815f7246006ef8c7d43'
     - remote_copy_folder_content_to_folder_after_change_actual.files[1].checksum == 'c79a6506c1c948be0d456ab5104d5e753ab2f3e6'
+
+# https://github.com/ansible/ansible/issues/50077
+- name: create empty nested directory
+  win_file:
+    path: '{{ test_win_copy_path }}\source\empty-nested\nested-dir'
+    state: directory
+
+- name: copy empty nested directory (check mode)
+  win_copy:
+    src: '{{ test_win_copy_path }}\source\empty-nested'
+    dest: '{{ test_win_copy_path }}\target'
+    remote_src: True
+  check_mode: True
+  register: copy_empty_dir_check
+
+- name: get result of copy empty nested directory (check mode)
+  win_stat:
+    path: '{{ test_win_copy_path }}\target\empty-nested'
+  register: copy_empty_dir_actual_check
+
+- name: assert copy empty nested directory (check mode)
+  assert:
+    that:
+    - copy_empty_dir_check is changed
+    - copy_empty_dir_check.operation == "folder_copy"
+    - not copy_empty_dir_actual_check.stat.exists
+
+- name: copy empty nested directory
+  win_copy:
+    src: '{{ test_win_copy_path }}\source\empty-nested'
+    dest: '{{ test_win_copy_path }}\target'
+    remote_src: True
+  register: copy_empty_dir
+
+- name: get result of copy empty nested directory
+  win_stat:
+    path: '{{ test_win_copy_path }}\target\empty-nested\nested-dir'
+  register: copy_empty_dir_actual
+
+- name: assert copy empty nested directory
+  assert:
+    that:
+    - copy_empty_dir is changed
+    - copy_empty_dir.operation == "folder_copy"
+    - copy_empty_dir_actual.stat.exists
+
+- name: copy empty nested directory (idempotent)
+  win_copy:
+    src: '{{ test_win_copy_path }}\source\empty-nested'
+    dest: '{{ test_win_copy_path }}\target'
+    remote_src: True
+  register: copy_empty_dir_again
+
+- name: assert copy empty nested directory (idempotent)
+  assert:
+    that:
+    - not copy_empty_dir_again is changed