diff --git a/changelogs/fragments/win_template-dest-dir-fix.yaml b/changelogs/fragments/win_template-dest-dir-fix.yaml
new file mode 100644
index 00000000000..84919d42a32
--- /dev/null
+++ b/changelogs/fragments/win_template-dest-dir-fix.yaml
@@ -0,0 +1,2 @@
+bugfixes:
+- win_template - fix when specifying the dest option as a directory with and without the trailing slash https://github.com/ansible/ansible/issues/39886
diff --git a/lib/ansible/modules/windows/win_copy.ps1 b/lib/ansible/modules/windows/win_copy.ps1
index a4e4e38c828..e142e5a5a20 100644
--- a/lib/ansible/modules/windows/win_copy.ps1
+++ b/lib/ansible/modules/windows/win_copy.ps1
@@ -368,7 +368,7 @@ if ($copy_mode -eq "query") {
     }
 
     # the dest parameter is a directory, we need to append original_basename
-    if ($dest.EndsWith("/") -or $dest.EndsWith("`\")) {
+    if ($dest.EndsWith("/") -or $dest.EndsWith("`\") -or (Test-Path -Path $dest -PathType Container)) {
         $remote_dest = Join-Path -Path $dest -ChildPath $original_basename
         $parent_dir = Split-Path -Path $remote_dest
 
diff --git a/lib/ansible/modules/windows/win_file.ps1 b/lib/ansible/modules/windows/win_file.ps1
index 3399b5e30bb..5ff30982ab0 100644
--- a/lib/ansible/modules/windows/win_file.ps1
+++ b/lib/ansible/modules/windows/win_file.ps1
@@ -15,6 +15,12 @@ $check_mode = Get-AnsibleParam -obj $params -name "_ansible_check_mode" -default
 $path = Get-AnsibleParam -obj $params -name "path" -type "path" -failifempty $true -aliases "dest","name"
 $state = Get-AnsibleParam -obj $params -name "state" -type "str" -validateset "absent","directory","file","touch"
 
+# used in template/copy when dest is the path to a dir and source is a file
+$original_basename = Get-AnsibleParam -obj $params -name "original_basename" -type "str"
+if ((Test-Path -Path $path -PathType Container) -and ($null -ne $original_basename)) {
+    $path = Join-Path -Path $path -ChildPath $original_basename
+}
+
 $result = @{
     changed = $false
 }
diff --git a/test/integration/targets/win_template/tasks/main.yml b/test/integration/targets/win_template/tasks/main.yml
index 1aa7995aff9..cd1829dfc4f 100644
--- a/test/integration/targets/win_template/tasks/main.yml
+++ b/test/integration/targets/win_template/tasks/main.yml
@@ -119,6 +119,105 @@
     that:
         - '"FC: no differences encountered" in diff_result.stdout'
 
+- name: create template dest directory
+  win_file:
+    path: '{{win_output_dir}}\directory'
+    state: directory
+
+- name: template src file to directory with backslash (check mode)
+  win_template:
+    src: foo.j2
+    dest: '{{win_output_dir}}\directory\'
+  check_mode: yes
+  register: template_to_dir_backslash_check
+
+- name: get result of template src file to directory with backslash (check_mode)
+  win_stat:
+    path: '{{win_output_dir}}\directory\foo.j2'
+  register: template_to_dir_backslash_result_check
+
+- name: assert template src file to directory with backslash (check mode)
+  assert:
+    that:
+    - template_to_dir_backslash_check is changed
+    - not template_to_dir_backslash_result_check.stat.exists
+
+- name: template src file to directory with backslash
+  win_template:
+    src: foo.j2
+    dest: '{{win_output_dir}}\directory\'
+  register: template_to_dir_backslash
+
+- name: get result of template src file to directory with backslash
+  win_stat:
+    path: '{{win_output_dir}}\directory\foo.j2'
+  register: template_to_dir_backslash_result
+
+- name: assert template src file to directory with backslash
+  assert:
+    that:
+    - template_to_dir_backslash is changed
+    - template_to_dir_backslash_result.stat.exists
+    - template_to_dir_backslash_result.stat.checksum == 'ed4f166b2937875ecad39c06648551f5af0b56d3'
+
+- name: template src file to directory with backslash (idempotent)
+  win_template:
+    src: foo.j2
+    dest: '{{win_output_dir}}\directory\'
+  register: template_to_dir_backslash_again
+
+- name: assert template src file to directory with backslash (idempotent)
+  assert:
+    that:
+    - not template_to_dir_backslash_again is changed
+
+- name: template src file to directory (check mode)
+  win_template:
+    src: another_foo.j2
+    dest: '{{win_output_dir}}\directory'
+  check_mode: yes
+  register: template_to_dir_check
+
+- name: get result of template src file to directory (check_mode)
+  win_stat:
+    path: '{{win_output_dir}}\directory\another_foo.j2'
+  register: template_to_dir_result_check
+
+- name: assert template src file to directory (check mode)
+  assert:
+    that:
+    - template_to_dir_check is changed
+    - not template_to_dir_result_check.stat.exists
+
+- name: template src file to directory
+  win_template:
+    src: another_foo.j2
+    dest: '{{win_output_dir}}\directory'
+  register: template_to_dir
+
+- name: get result of template src file to directory
+  win_stat:
+    path: '{{win_output_dir}}\directory\another_foo.j2'
+  register: template_to_dir_result
+
+- name: assert template src file to directory with
+  assert:
+    that:
+    - template_to_dir is changed
+    - template_to_dir_result.stat.exists
+    - template_to_dir_result.stat.checksum == 'b10b6f27290d554a77da2457b2ccd7d6de86b920'
+
+- name: template src file to directory (idempotent)
+  win_template:
+    src: another_foo.j2
+    dest: '{{win_output_dir}}\directory'
+  register: template_to_dir_again
+
+- name: assert template src file to directory (idempotent)
+  assert:
+    that:
+    - not template_to_dir_again is changed
+
 # VERIFY MODE
 # can't set file mode on windows so commenting this test out
 #- name: set file mode
diff --git a/test/integration/targets/win_template/templates/another_foo.j2 b/test/integration/targets/win_template/templates/another_foo.j2
new file mode 100644
index 00000000000..4ee9bca2d76
--- /dev/null
+++ b/test/integration/targets/win_template/templates/another_foo.j2
@@ -0,0 +1,3 @@
+ABC
+{{ templated_var }}
+DEF