diff --git a/.azure-pipelines/azure-pipelines.yml b/.azure-pipelines/azure-pipelines.yml
index 7ed7a312b49..bf4482333d9 100644
--- a/.azure-pipelines/azure-pipelines.yml
+++ b/.azure-pipelines/azure-pipelines.yml
@@ -68,9 +68,11 @@ stages:
           nameFormat: Server {0}
           testFormat: windows/{0}/1
           targets:
-            - test: 2016
-            - test: 2019
-            - test: 2022
+            - test: 2016/winrm/http
+            - test: 2019/winrm/https
+            - test: 2022/winrm/https
+            - test: 2022/psrp/http
+            - test: 2022/ssh/key
   - stage: Remote
     dependsOn: []
     jobs:
@@ -181,9 +183,11 @@ stages:
           nameFormat: Server {0}
           testFormat: i/windows/{0}
           targets:
-            - test: 2016
-            - test: 2019
-            - test: 2022
+            - test: 2016/winrm/http
+            - test: 2019/winrm/https
+            - test: 2022/winrm/https
+            - test: 2022/psrp/http
+            - test: 2022/ssh/key
   - stage: Incidental
     dependsOn: []
     jobs:
diff --git a/.azure-pipelines/commands/incidental/windows.sh b/.azure-pipelines/commands/incidental/windows.sh
index 24272f62baf..f5a3070c457 100755
--- a/.azure-pipelines/commands/incidental/windows.sh
+++ b/.azure-pipelines/commands/incidental/windows.sh
@@ -6,6 +6,8 @@ declare -a args
 IFS='/:' read -ra args <<< "$1"
 
 version="${args[1]}"
+connection="${args[2]}"
+connection_setting="${args[3]}"
 
 target="shippable/windows/incidental/"
 
@@ -26,11 +28,7 @@ if [ -s /tmp/windows.txt ] || [ "${CHANGED:+$CHANGED}" == "" ]; then
     echo "Detected changes requiring integration tests specific to Windows:"
     cat /tmp/windows.txt
 
-    echo "Running Windows integration tests for multiple versions concurrently."
-
-    platforms=(
-        --windows "${version}"
-    )
+    echo "Running Windows integration tests for the version ${version}."
 else
     echo "No changes requiring integration tests specific to Windows were detected."
     echo "Running Windows integration tests for a single version only: ${single_version}"
@@ -39,14 +37,10 @@ else
         echo "Skipping this job since it is for: ${version}"
         exit 0
     fi
-
-    platforms=(
-        --windows "${version}"
-    )
 fi
 
 # shellcheck disable=SC2086
 ansible-test windows-integration --color -v --retry-on-error "${target}" ${COVERAGE:+"$COVERAGE"} ${CHANGED:+"$CHANGED"} ${UNSTABLE:+"$UNSTABLE"} \
-    "${platforms[@]}" \
-    --docker default --python "${python_default}" \
-    --remote-terminate always --remote-stage "${stage}" --remote-provider "${provider}"
+    --controller "docker:default,python=${python_default}" \
+    --target "remote:windows/${version},connection=${connection}+${connection_setting},provider=${provider}" \
+    --remote-terminate always --remote-stage "${stage}"
diff --git a/.azure-pipelines/commands/windows.sh b/.azure-pipelines/commands/windows.sh
index 693d4f24bdc..622eb9e2d5e 100755
--- a/.azure-pipelines/commands/windows.sh
+++ b/.azure-pipelines/commands/windows.sh
@@ -6,7 +6,9 @@ declare -a args
 IFS='/:' read -ra args <<< "$1"
 
 version="${args[1]}"
-group="${args[2]}"
+connection="${args[2]}"
+connection_setting="${args[3]}"
+group="${args[4]}"
 
 target="shippable/windows/group${group}/"
 
@@ -31,11 +33,7 @@ if [ -s /tmp/windows.txt ] || [ "${CHANGED:+$CHANGED}" == "" ]; then
     echo "Detected changes requiring integration tests specific to Windows:"
     cat /tmp/windows.txt
 
-    echo "Running Windows integration tests for multiple versions concurrently."
-
-    platforms=(
-        --windows "${version}"
-    )
+    echo "Running Windows integration tests for the version ${version}."
 else
     echo "No changes requiring integration tests specific to Windows were detected."
     echo "Running Windows integration tests for a single version only: ${single_version}"
@@ -44,17 +42,13 @@ else
         echo "Skipping this job since it is for: ${version}"
         exit 0
     fi
-
-    platforms=(
-        --windows "${version}"
-    )
 fi
 
-for version in "${python_versions[@]}"; do
+for py_version in "${python_versions[@]}"; do
     changed_all_target="all"
     changed_all_mode="default"
 
-    if [ "${version}" == "${python_default}" ]; then
+    if [ "${py_version}" == "${python_default}" ]; then
         # smoketest tests
         if [ "${CHANGED}" ]; then
             # with change detection enabled run tests for anything changed
@@ -80,7 +74,7 @@ for version in "${python_versions[@]}"; do
     fi
 
     # terminate remote instances on the final python version tested
-    if [ "${version}" = "${python_versions[-1]}" ]; then
+    if [ "${py_version}" = "${python_versions[-1]}" ]; then
         terminate="always"
     else
         terminate="never"
@@ -88,7 +82,8 @@ for version in "${python_versions[@]}"; do
 
     # shellcheck disable=SC2086
     ansible-test windows-integration --color -v --retry-on-error "${ci}" ${COVERAGE:+"$COVERAGE"} ${CHANGED:+"$CHANGED"} ${UNSTABLE:+"$UNSTABLE"} \
-        "${platforms[@]}" --changed-all-target "${changed_all_target}" --changed-all-mode "${changed_all_mode}" \
-        --docker default --python "${version}" \
-        --remote-terminate "${terminate}" --remote-stage "${stage}" --remote-provider "${provider}"
+        --changed-all-target "${changed_all_target}" --changed-all-mode "${changed_all_mode}" \
+        --controller "docker:default,python=${py_version}" \
+        --target "remote:windows/${version},connection=${connection}+${connection_setting},provider=${provider}" \
+        --remote-terminate "${terminate}" --remote-stage "${stage}"
 done
diff --git a/changelogs/fragments/ssh-windows.yml b/changelogs/fragments/ssh-windows.yml
new file mode 100644
index 00000000000..678f4b4603f
--- /dev/null
+++ b/changelogs/fragments/ssh-windows.yml
@@ -0,0 +1,13 @@
+breaking_changes:
+- >-
+  Stopped wrapping all commands sent over SSH on a Windows target with a
+  ``powershell.exe`` executable. This results in one less process being started
+  on each command for Windows to improve efficiency, simplify the code, and
+  make ``raw`` an actual raw command run with the default shell configured on
+  the Windows sshd settings. This should have no affect on most tasks except
+  for ``raw`` which now is not guaranteed to always be running in a PowerShell
+  shell and from having the console output codepage set to UTF-8. To avoid this
+  issue either swap to using ``ansible.windows.win_command``,
+  ``ansible.windows.win_shell``, ``ansible.windows.win_powershell`` or manually
+  wrap the raw command with the shell commands needed to set the output console
+  encoding.
diff --git a/lib/ansible/executor/powershell/become_wrapper.ps1 b/lib/ansible/executor/powershell/become_wrapper.ps1
index f40e2658f5f..cea42c128aa 100644
--- a/lib/ansible/executor/powershell/become_wrapper.ps1
+++ b/lib/ansible/executor/powershell/become_wrapper.ps1
@@ -116,12 +116,11 @@ Write-AnsibleLog "INFO - parsed become input, user: '$username', type: '$logon_t
 # set to Stop and cannot be changed. Also need to split the payload from the wrapper to prevent potentially
 # sensitive content from being logged by the scriptblock logger.
 $bootstrap_wrapper = {
-    &chcp.com 65001 > $null
-    $exec_wrapper_str = [System.Console]::In.ReadToEnd()
-    $split_parts = $exec_wrapper_str.Split(@("`0`0`0`0"), 2, [StringSplitOptions]::RemoveEmptyEntries)
+    [Console]::InputEncoding = [Console]::OutputEncoding = New-Object System.Text.UTF8Encoding
+    $ew = [System.Console]::In.ReadToEnd()
+    $split_parts = $ew.Split(@("`0`0`0`0"), 2, [StringSplitOptions]::RemoveEmptyEntries)
     Set-Variable -Name json_raw -Value $split_parts[1]
-    $exec_wrapper = [ScriptBlock]::Create($split_parts[0])
-    &$exec_wrapper
+    &([ScriptBlock]::Create($split_parts[0]))
 }
 $exec_command = [System.Convert]::ToBase64String([System.Text.Encoding]::Unicode.GetBytes($bootstrap_wrapper.ToString()))
 $lp_command_line = "powershell.exe -NonInteractive -NoProfile -ExecutionPolicy Bypass -EncodedCommand $exec_command"
diff --git a/lib/ansible/executor/powershell/bootstrap_wrapper.ps1 b/lib/ansible/executor/powershell/bootstrap_wrapper.ps1
index cdba80cbb01..8e7141eb515 100644
--- a/lib/ansible/executor/powershell/bootstrap_wrapper.ps1
+++ b/lib/ansible/executor/powershell/bootstrap_wrapper.ps1
@@ -1,4 +1,4 @@
-&chcp.com 65001 > $null
+try { [Console]::InputEncoding = [Console]::OutputEncoding = New-Object System.Text.UTF8Encoding } catch { $null = $_ }
 
 if ($PSVersionTable.PSVersion -lt [Version]"3.0") {
     '{"failed":true,"msg":"Ansible requires PowerShell v3.0 or newer"}'
@@ -9,5 +9,4 @@ $exec_wrapper_str = $input | Out-String
 $split_parts = $exec_wrapper_str.Split(@("`0`0`0`0"), 2, [StringSplitOptions]::RemoveEmptyEntries)
 If (-not $split_parts.Length -eq 2) { throw "invalid payload" }
 Set-Variable -Name json_raw -Value $split_parts[1]
-$exec_wrapper = [ScriptBlock]::Create($split_parts[0])
-&$exec_wrapper
+& ([ScriptBlock]::Create($split_parts[0]))
diff --git a/lib/ansible/plugins/connection/ssh.py b/lib/ansible/plugins/connection/ssh.py
index 4c58e0d9470..83ff03631e6 100644
--- a/lib/ansible/plugins/connection/ssh.py
+++ b/lib/ansible/plugins/connection/ssh.py
@@ -1306,14 +1306,6 @@ class Connection(ConnectionBase):
             # prompt that will not occur
             sudoable = False
 
-            # Make sure our first command is to set the console encoding to
-            # utf-8, this must be done via chcp to get utf-8 (65001)
-            # union-attr ignores rely on internal powershell shell plugin details,
-            # this should be fixed at a future point in time.
-            cmd_parts = ["chcp.com", "65001", self._shell._SHELL_REDIRECT_ALLNULL, self._shell._SHELL_AND]  # type: ignore[union-attr]
-            cmd_parts.extend(self._shell._encode_script(cmd, as_list=True, strict_mode=False, preserve_rc=False))  # type: ignore[union-attr]
-            cmd = ' '.join(cmd_parts)
-
         # we can only use tty when we are not pipelining the modules. piping
         # data into /usr/bin/python inside a tty automatically invokes the
         # python interactive-mode but the modules are not compatible with the
diff --git a/lib/ansible/plugins/shell/powershell.py b/lib/ansible/plugins/shell/powershell.py
index 153f5a6ca53..22ba2ca5373 100644
--- a/lib/ansible/plugins/shell/powershell.py
+++ b/lib/ansible/plugins/shell/powershell.py
@@ -100,6 +100,8 @@ class ShellModule(ShellBase):
     # Family of shells this has.  Must match the filename without extension
     SHELL_FAMILY = 'powershell'
 
+    # We try catch as some connection plugins don't have a console (PSRP).
+    _CONSOLE_ENCODING = "try { [Console]::OutputEncoding = New-Object System.Text.UTF8Encoding } catch {}"
     _SHELL_REDIRECT_ALLNULL = '> $null'
     _SHELL_AND = ';'
 
@@ -157,13 +159,14 @@ class ShellModule(ShellBase):
         if not basefile:
             basefile = self.__class__._generate_temp_dir_name()
         basefile = self._escape(self._unquote(basefile))
-        basetmpdir = tmpdir if tmpdir else self.get_option('remote_tmp')
+        basetmpdir = self._escape(tmpdir if tmpdir else self.get_option('remote_tmp'))
 
-        script = '''
-        $tmp_path = [System.Environment]::ExpandEnvironmentVariables('%s')
-        $tmp = New-Item -Type Directory -Path $tmp_path -Name '%s'
+        script = f'''
+        {self._CONSOLE_ENCODING}
+        $tmp_path = [System.Environment]::ExpandEnvironmentVariables('{basetmpdir}')
+        $tmp = New-Item -Type Directory -Path $tmp_path -Name '{basefile}'
         Write-Output -InputObject $tmp.FullName
-        ''' % (basetmpdir, basefile)
+        '''
         return self._encode_script(script.strip())
 
     def expand_user(self, user_home_path, username=''):
@@ -177,7 +180,7 @@ class ShellModule(ShellBase):
             script = "Write-Output ((Get-Location).Path + '%s')" % self._escape(user_home_path[1:])
         else:
             script = "Write-Output '%s'" % self._escape(user_home_path)
-        return self._encode_script(script)
+        return self._encode_script(f"{self._CONSOLE_ENCODING}; {script}")
 
     def exists(self, path):
         path = self._escape(self._unquote(path))
diff --git a/test/integration/targets/connection/test_connection.yml b/test/integration/targets/connection/test_connection.yml
index 470b38921fe..a24bcf63ae0 100644
--- a/test/integration/targets/connection/test_connection.yml
+++ b/test/integration/targets/connection/test_connection.yml
@@ -17,6 +17,7 @@
                 plugin_type="connection",
             ) == "scp"
         }}
+      echo_string: 汉语
 
   - name: set test filename
     set_fact:
@@ -25,12 +26,19 @@
   ### raw with unicode arg and output
 
   - name: raw with unicode arg and output
-    raw: echo 汉语
+    raw: "{{ echo_commands[action_prefix ~ ansible_connection ~ '_' ~ (ansible_shell_type|default(''))] | default(echo_commands['default']) }}"
+    vars:
+      # Windows over SSH does not have a way to set the console codepage to allow UTF-8. We need to
+      # wrap the commands we send to the remote host to get it working.
+      echo_commands:
+        win_ssh_powershell: '[Console]::OutputEncoding = [System.Text.Encoding]::UTF8; echo {{ echo_string }}'
+        win_ssh_cmd: 'powershell.exe -Command "[Console]::OutputEncoding = [System.Text.Encoding]::UTF8; echo {{ echo_string }}"'
+        default: echo {{ echo_string }}
     register: command
   - name: check output of raw with unicode arg and output
     assert:
       that:
-      - "'汉语' in command.stdout"
+      - echo_string in command.stdout
       - command is changed # as of 2.2, raw should default to changed: true for consistency w/ shell/command/script modules
 
   ### copy local file with unicode filename and content
diff --git a/test/integration/targets/win_raw/tasks/main.yml b/test/integration/targets/win_raw/tasks/main.yml
index 5c51c0a06f3..a4e93f25e49 100644
--- a/test/integration/targets/win_raw/tasks/main.yml
+++ b/test/integration/targets/win_raw/tasks/main.yml
@@ -25,7 +25,7 @@
     that:
       - "getmac_result.rc == 0"
       - "getmac_result.stdout"
-      - "not getmac_result.stderr"
+      - (ansible_connection == 'ssh') | ternary(getmac_result.stderr is defined, not getmac_result.stderr)
       - "getmac_result is not failed"
       - "getmac_result is changed"
 
@@ -39,7 +39,7 @@
       - "ipconfig_result.rc == 0"
       - "ipconfig_result.stdout"
       - "'Physical Address' in ipconfig_result.stdout"
-      - "not ipconfig_result.stderr"
+      - (ansible_connection == 'ssh') | ternary(ipconfig_result.stderr is defined, not ipconfig_result.stderr)
       - "ipconfig_result is not failed"
       - "ipconfig_result is changed"
 
@@ -80,7 +80,7 @@
     that:
       - "sleep_command.rc == 0"
       - "not sleep_command.stdout"
-      - "not sleep_command.stderr"
+      - (ansible_connection == 'ssh') | ternary(sleep_command.stderr is defined, not sleep_command.stderr)
       - "sleep_command is not failed"
       - "sleep_command is changed"
 
@@ -93,11 +93,14 @@
     that:
       - "raw_result.stdout_lines[0] == 'wwe=raw'"
 
+# ssh cannot pre-set the codepage so we need to do it in the command.
 - name: unicode tests for winrm
   when: ansible_connection != 'psrp'  # Write-Host does not work over PSRP
   block:
   - name: run a raw command with unicode chars and quoted args (from https://github.com/ansible/ansible-modules-core/issues/1929)
-    raw: Write-Host --% icacls D:\somedir\ /grant "! ЗАО. Руководство":F
+    raw: |
+      {{ (ansible_connection == 'ssh') | ternary("[Console]::OutputEncoding = [System.Text.Encoding]::UTF8", "") }}
+      Write-Host --% icacls D:\somedir\ /grant "! ЗАО. Руководство":F
     register: raw_result2
 
   - name: make sure raw passes command as-is and doesn't split/rejoin args
diff --git a/test/integration/targets/win_script/tasks/main.yml b/test/integration/targets/win_script/tasks/main.yml
index 4d57eda2ba3..d1082e72e8e 100644
--- a/test/integration/targets/win_script/tasks/main.yml
+++ b/test/integration/targets/win_script/tasks/main.yml
@@ -38,7 +38,7 @@
       - "test_script_result.rc == 0"
       - "test_script_result.stdout"
       - "'Woohoo' in test_script_result.stdout"
-      - "not test_script_result.stderr"
+      - (ansible_connection == 'ssh') | ternary(test_script_result.stderr is defined, not test_script_result.stderr)
       - "test_script_result is not failed"
       - "test_script_result is changed"
 
@@ -54,7 +54,7 @@
       - "test_script_with_args_result.stdout_lines[0] == '/this'"
       - "test_script_with_args_result.stdout_lines[1] == '/that'"
       - "test_script_with_args_result.stdout_lines[2] == '/Ӧther'"
-      - "not test_script_with_args_result.stderr"
+      - (ansible_connection == 'ssh') | ternary(test_script_with_args_result.stderr is defined, not test_script_with_args_result.stderr)
       - "test_script_with_args_result is not failed"
       - "test_script_with_args_result is changed"
 
@@ -71,7 +71,7 @@
   assert:
     that:
     - test_script_with_large_args_result.rc == 0
-    - not test_script_with_large_args_result.stderr
+    - (ansible_connection == 'ssh') | ternary(test_script_with_large_args_result.stderr is defined, not test_script_with_large_args_result.stderr)
     - test_script_with_large_args_result is not failed
     - test_script_with_large_args_result is changed
 
@@ -99,7 +99,7 @@
       - "test_script_with_splatting_result.stdout_lines[0] == 'this'"
       - "test_script_with_splatting_result.stdout_lines[1] == test_win_script_value"
       - "test_script_with_splatting_result.stdout_lines[2] == 'other'"
-      - "not test_script_with_splatting_result.stderr"
+      - (ansible_connection == 'ssh') | ternary(test_script_with_splatting_result.stderr is defined, not test_script_with_splatting_result.stderr)
       - "test_script_with_splatting_result is not failed"
       - "test_script_with_splatting_result is changed"
 
@@ -115,7 +115,7 @@
       - "test_script_with_splatting2_result.stdout_lines[0] == 'THIS'"
       - "test_script_with_splatting2_result.stdout_lines[1] == 'THAT'"
       - "test_script_with_splatting2_result.stdout_lines[2] == 'OTHER'"
-      - "not test_script_with_splatting2_result.stderr"
+      - (ansible_connection == 'ssh') | ternary(test_script_with_splatting2_result.stderr is defined, not test_script_with_splatting2_result.stderr)
       - "test_script_with_splatting2_result is not failed"
       - "test_script_with_splatting2_result is changed"
 
@@ -148,7 +148,7 @@
     that:
       - "test_script_creates_file_result.rc == 0"
       - "not test_script_creates_file_result.stdout"
-      - "not test_script_creates_file_result.stderr"
+      - (ansible_connection == 'ssh') | ternary(test_script_creates_file_result.stderr is defined, not test_script_creates_file_result.stderr)
       - "test_script_creates_file_result is not failed"
       - "test_script_creates_file_result is changed"
 
@@ -176,7 +176,7 @@
     that:
       - "test_script_removes_file_result.rc == 0"
       - "not test_script_removes_file_result.stdout"
-      - "not test_script_removes_file_result.stderr"
+      - (ansible_connection == 'ssh') | ternary(test_script_removes_file_result.stderr is defined, not test_script_removes_file_result.stderr)
       - "test_script_removes_file_result is not failed"
       - "test_script_removes_file_result is changed"
 
@@ -205,7 +205,7 @@
         - "test_batch_result.rc == 0"
         - "test_batch_result.stdout"
         - "'batch' in test_batch_result.stdout"
-        - "not test_batch_result.stderr"
+        - (ansible_connection == 'ssh') | ternary(test_batch_result.stderr is defined, not test_batch_result.stderr)
         - "test_batch_result is not failed"
         - "test_batch_result is changed"
 
@@ -219,7 +219,7 @@
         - "test_cmd_result.rc == 0"
         - "test_cmd_result.stdout"
         - "'cmd extension' in test_cmd_result.stdout"
-        - "not test_cmd_result.stderr"
+        - (ansible_connection == 'ssh') | ternary(test_cmd_result.stderr is defined, not test_cmd_result.stderr)
         - "test_cmd_result is not failed"
         - "test_cmd_result is changed"
 
diff --git a/test/integration/targets/windows-minimal/aliases b/test/integration/targets/windows-minimal/aliases
index 479948a194e..7bb1af0fd89 100644
--- a/test/integration/targets/windows-minimal/aliases
+++ b/test/integration/targets/windows-minimal/aliases
@@ -1,4 +1,5 @@
 shippable/windows/group1
 shippable/windows/minimal
 shippable/windows/smoketest
+needs/target/setup_remote_tmp_dir
 windows
diff --git a/test/integration/targets/windows-minimal/meta/main.yml b/test/integration/targets/windows-minimal/meta/main.yml
new file mode 100644
index 00000000000..1810d4bec98
--- /dev/null
+++ b/test/integration/targets/windows-minimal/meta/main.yml
@@ -0,0 +1,2 @@
+dependencies:
+  - setup_remote_tmp_dir
diff --git a/test/integration/targets/windows-minimal/tasks/main.yml b/test/integration/targets/windows-minimal/tasks/main.yml
index 1e075d7a61b..9a3e83e8313 100644
--- a/test/integration/targets/windows-minimal/tasks/main.yml
+++ b/test/integration/targets/windows-minimal/tasks/main.yml
@@ -85,3 +85,35 @@
   ansible.windows.win_shell: echo "name=foo"
   register: win_shell_collection_res
   failed_when: win_shell_collection_res.stdout | trim != 'name=foo'
+
+- name: set ping data fact
+  set_fact:
+    # FUTURE: Fix psrp so it can handle non-ASCII chars in a non-pipeline scenario
+    ping_data: '{{ (ansible_connection == "psrp") | ternary("test", "汉语") }}'
+
+- name: run module with pipelining disabled
+  ansible.builtin.command:
+    cmd: >-
+      ansible windows
+      -m ansible.windows.win_ping
+      -a 'data={{ ping_data }}'
+      -i {{ '-i '.join(ansible_inventory_sources) }}
+      {{ '' if not ansible_verbosity else '-' ~ ('v' * ansible_verbosity) }}
+      -e ansible_remote_tmp='{{ remote_tmp_dir | regex_replace('\\', '\\\\') }}'
+  register: pipeline_disabled_res
+  delegate_to: localhost
+  environment:
+    ANSIBLE_KEEP_REMOTE_FILES: 'true'
+    ANSIBLE_NOCOLOR: 'true'
+    ANSIBLE_FORCE_COLOR: 'false'
+
+- name: view temp files
+  ansible.windows.win_shell: (Get-Item '{{ remote_tmp_dir }}\ansible-tmp-*\*').Name
+  register: pipeline_disabled_files
+
+- name: assert run module with pipelining disabled
+  assert:
+    that:
+    - >-
+      pipeline_disabled_res.stdout is search('\"ping\": \"' ~ ping_data ~ '\"')
+    - pipeline_disabled_files.stdout_lines == ["AnsiballZ_win_ping.ps1"]