diff --git a/.azure-pipelines/azure-pipelines.yml b/.azure-pipelines/azure-pipelines.yml
index e3df5b7388b..a22e98e5ac1 100644
--- a/.azure-pipelines/azure-pipelines.yml
+++ b/.azure-pipelines/azure-pipelines.yml
@@ -69,8 +69,6 @@ stages:
           nameFormat: Server {0}
           testFormat: windows/{0}/1
           targets:
-            - name: 2016 WinRM HTTP WinPS
-              test: 2016/winrm/http/5.1
             - name: 2019 WinRM HTTPS WinPS
               test: 2019/winrm/https/5.1
             - name: 2022 WinRM HTTPS WinPS
@@ -234,8 +232,6 @@ stages:
           nameFormat: Server {0}
           testFormat: i/windows/{0}
           targets:
-            - name: 2016 WinRM HTTP WinPS
-              test: 2016/winrm/http/5.1
             - name: 2019 WinRM HTTPS WinPS
               test: 2019/winrm/https/5.1
             - name: 2022 WinRM HTTPS WinPS
diff --git a/changelogs/fragments/ansible-test-windows-server-2016.yml b/changelogs/fragments/ansible-test-windows-server-2016.yml
new file mode 100644
index 00000000000..fefdd209073
--- /dev/null
+++ b/changelogs/fragments/ansible-test-windows-server-2016.yml
@@ -0,0 +1,2 @@
+minor_changes:
+  - ansible-test - Remove support for Windows Server 2016 managed remote.
diff --git a/changelogs/fragments/psrp-2016.yml b/changelogs/fragments/psrp-2016.yml
new file mode 100644
index 00000000000..28574b3f1a7
--- /dev/null
+++ b/changelogs/fragments/psrp-2016.yml
@@ -0,0 +1,2 @@
+minor_changes:
+  - psrp connection plugin - Remove explicit error handling support for Windows Server 2016.
diff --git a/lib/ansible/plugins/connection/psrp.py b/lib/ansible/plugins/connection/psrp.py
index 6ec36728fb6..abfd71d1305 100644
--- a/lib/ansible/plugins/connection/psrp.py
+++ b/lib/ansible/plugins/connection/psrp.py
@@ -746,17 +746,7 @@ class Connection(ConnectionBase):
             # NativeCommandError and NativeCommandErrorMessage are special
             # cases used for stderr from a subprocess, we will just print the
             # error message
-            if error.fq_error == 'NativeCommandErrorMessage' and not error.target_name:
-                # This can be removed once Server 2016 is EOL and no longer
-                # supported. PS 5.1 on 2016 will emit 1 error record under
-                # NativeCommandError being the first line, subsequent records
-                # are the raw stderr up to 4096 chars. Each entry is the raw
-                # stderr value without any newlines appended so we just use the
-                # value as is. We know it's 2016 as the target_name is empty in
-                # this scenario.
-                stderr_list.append(str(error))
-                continue
-            elif error.fq_error in ['NativeCommandError', 'NativeCommandErrorMessage']:
+            if error.fq_error in ['NativeCommandError', 'NativeCommandErrorMessage']:
                 stderr_list.append(f"{error}\r\n")
                 continue
 
diff --git a/test/integration/targets/module_utils_Ansible.Basic/library/ansible_basic_tests.ps1 b/test/integration/targets/module_utils_Ansible.Basic/library/ansible_basic_tests.ps1
index a013513f541..968f455ab0b 100644
--- a/test/integration/targets/module_utils_Ansible.Basic/library/ansible_basic_tests.ps1
+++ b/test/integration/targets/module_utils_Ansible.Basic/library/ansible_basic_tests.ps1
@@ -2045,33 +2045,10 @@ test_no_log - Invoked with:
             $output = [Ansible.Basic.AnsibleModule]::FromJson($_.Exception.InnerException.Output)
         }
 
-        if ([System.Environment]::OSVersion.Version -lt [Version]'10.0') {
-            # Older hosts can only do delete on close. This means Dir1 and its
-            # file will still be present but Dir2 should be deleted.
-            $expected_msg = "Failure cleaning temp path '$actual_tmpdir': IOException Directory contains files still open by other processes"
-            $output.warnings.Count | Assert-Equal -Expected 1
-            $output.warnings[0] | Assert-Equal -Expected $expected_msg
+        (Test-Path -LiteralPath $actual_tmpdir -PathType Container) | Assert-Equal -Expected $false
+        $output.warnings.Count | Assert-Equal -Expected 0
 
-            (Test-Path -LiteralPath $actual_tmpdir -PathType Container) | Assert-Equal -Expected $true
-            (Test-Path -LiteralPath $dir1 -PathType Container) | Assert-Equal -Expected $true
-            # Test-Path tries to open the file in a way that fails if it's marked as deleted
-            (Get-ChildItem -LiteralPath $dir1 -File).Count | Assert-Equal -Expected 1
-            (Test-Path -LiteralPath $dir2 -PathType Container) | Assert-Equal -Expected $false
-            (Test-Path -LiteralPath $file3 -PathType Leaf) | Assert-Equal -Expected $false
-
-            # Releasing the file handle releases the lock on the file deleting
-            # it. Unfortunately the parent dir will still be present
-            $fs.Dispose()
-            (Test-Path -LiteralPath $dir1 -PathType Container) | Assert-Equal -Expected $true
-            (Test-Path -LiteralPath $file1 -PathType Leaf) | Assert-Equal -Expected $false
-        }
-        else {
-            # Server 2016+ can use the POSIX APIs which will delete it straight away
-            (Test-Path -LiteralPath $actual_tmpdir -PathType Container) | Assert-Equal -Expected $false
-            $output.warnings.Count | Assert-Equal -Expected 0
-
-            $fs.Dispose()
-        }
+        $fs.Dispose()
 
         Remove-Item -LiteralPath $remote_tmp -Force -Recurse
     }
diff --git a/test/integration/targets/win_app_control/main.yml b/test/integration/targets/win_app_control/main.yml
index 7dd1ca958cf..4297284191c 100644
--- a/test/integration/targets/win_app_control/main.yml
+++ b/test/integration/targets/win_app_control/main.yml
@@ -20,14 +20,7 @@
       - ansible_install_dir is defined
       - local_tmp_dir is defined
 
-  - name: get OS version
-    ansible.windows.win_powershell:
-      script: (Get-Item -LiteralPath $env:SystemRoot\System32\kernel32.dll).VersionInfo.ProductVersion.ToString()
-    register: os_version
-
-  - name: setup and test block for 2019 and later
-    when:
-    - os_version.output[0] is version('10.0.17763', '>=')  # 2019+
+  - name: setup and test block
     block:
     - name: get test remote tmp dir
       import_role:
diff --git a/test/integration/targets/win_script/tasks/main.yml b/test/integration/targets/win_script/tasks/main.yml
index e27760395d0..c2aecb9e1e3 100644
--- a/test/integration/targets/win_script/tasks/main.yml
+++ b/test/integration/targets/win_script/tasks/main.yml
@@ -335,9 +335,9 @@
     that:
     - script_stderr.rc == 0
     - script_stderr.stdout == ""
-    # SSH includes debug output in stderr, and WinRM on 2016 includes a trailing newline
+    # SSH includes debug output in stderr and includes a trailing newline
     # Use a simple search to ensure the expected stderr is present but ignoring any extra output
-    - script_stderr.stderr is search("stderr 1\r\nstderr 2\r\n")
+    - script_stderr.stderr == "stderr 1\r\nstderr 2\r\n"
 
 - name: run script with non-ASCII contents
   script: test_script_unicode.ps1
diff --git a/test/lib/ansible_test/_data/completion/windows.txt b/test/lib/ansible_test/_data/completion/windows.txt
index a822dcecf10..7ade69e27e5 100644
--- a/test/lib/ansible_test/_data/completion/windows.txt
+++ b/test/lib/ansible_test/_data/completion/windows.txt
@@ -1,4 +1,3 @@
-windows/2016 provider=aws arch=x86_64 connection=winrm+http
 windows/2019 provider=aws arch=x86_64 connection=winrm+https
 windows/2022 provider=aws arch=x86_64 connection=winrm+https
 windows/2025 provider=aws arch=x86_64 connection=psrp+http alias=windows/latest