diff --git a/Doc/library/asyncio-eventloop.rst b/Doc/library/asyncio-eventloop.rst
index 943683f6b8a7f6..8d7d0377c132b8 100644
--- a/Doc/library/asyncio-eventloop.rst
+++ b/Doc/library/asyncio-eventloop.rst
@@ -1791,7 +1791,7 @@ By default asyncio is configured to use :class:`EventLoop`.
    .. seealso::
 
       `MSDN documentation on I/O Completion Ports
-      <https://docs.microsoft.com/en-ca/windows/desktop/FileIO/i-o-completion-ports>`_.
+      <https://learn.microsoft.com/windows/win32/fileio/i-o-completion-ports>`_.
 
 .. class:: EventLoop
 
diff --git a/Doc/library/time.rst b/Doc/library/time.rst
index 9cd5db768e9853..6265c2214eaa0d 100644
--- a/Doc/library/time.rst
+++ b/Doc/library/time.rst
@@ -390,7 +390,7 @@ Functions
    threads ready to run, the function returns immediately, and the thread
    continues execution.  On Windows 8.1 and newer the implementation uses
    a `high-resolution timer
-   <https://docs.microsoft.com/en-us/windows-hardware/drivers/kernel/high-resolution-timers>`_
+   <https://learn.microsoft.com/windows-hardware/drivers/kernel/high-resolution-timers>`_
    which provides resolution of 100 nanoseconds. If *secs* is zero, ``Sleep(0)`` is used.
 
    Unix implementation:
diff --git a/Doc/using/windows.rst b/Doc/using/windows.rst
index b9757ad776db27..63ce7f5d4ffb52 100644
--- a/Doc/using/windows.rst
+++ b/Doc/using/windows.rst
@@ -434,7 +434,7 @@ When writing to the Windows Registry, the following behaviors exist:
 For more detail on the technical basis for these limitations, please consult
 Microsoft's documentation on packaged full-trust apps, currently available at
 `docs.microsoft.com/en-us/windows/msix/desktop/desktop-to-uwp-behind-the-scenes
-<https://docs.microsoft.com/en-us/windows/msix/desktop/desktop-to-uwp-behind-the-scenes>`_
+<https://learn.microsoft.com/windows/msix/desktop/desktop-to-uwp-behind-the-scenes>`_
 
 
 .. _windows-nuget:
@@ -535,7 +535,7 @@ dependents, such as Idle), pip and the Python documentation are not included.
 .. note::
 
     The embedded distribution does not include the `Microsoft C Runtime
-    <https://docs.microsoft.com/en-US/cpp/windows/latest-supported-vc-redist#visual-studio-2015-2017-2019-and-2022>`_ and it is
+    <https://learn.microsoft.com/cpp/windows/latest-supported-vc-redist#visual-studio-2015-2017-2019-and-2022>`_ and it is
     the responsibility of the application installer to provide this. The
     runtime may have already been installed on a user's system previously or
     automatically via Windows Update, and can be detected by finding
@@ -678,13 +678,13 @@ System variables, you need non-restricted access to your machine
 
 .. seealso::
 
-    https://docs.microsoft.com/en-us/windows/win32/procthread/environment-variables
+    https://learn.microsoft.com/windows/win32/procthread/environment-variables
       Overview of environment variables on Windows
 
-    https://docs.microsoft.com/en-us/windows-server/administration/windows-commands/set_1
+    https://learn.microsoft.com/windows-server/administration/windows-commands/set_1
       The ``set`` command, for temporarily modifying environment variables
 
-    https://docs.microsoft.com/en-us/windows-server/administration/windows-commands/setx
+    https://learn.microsoft.com/windows-server/administration/windows-commands/setx
       The ``setx`` command, for permanently modifying environment variables
 
 
@@ -1290,13 +1290,13 @@ is a collection of modules for advanced Windows-specific support.  This includes
 utilities for:
 
 * `Component Object Model
-  <https://docs.microsoft.com/en-us/windows/win32/com/component-object-model--com--portal>`_
+  <https://learn.microsoft.com/windows/win32/com/component-object-model--com--portal>`_
   (COM)
 * Win32 API calls
 * Registry
 * Event log
 * `Microsoft Foundation Classes
-  <https://docs.microsoft.com/en-us/cpp/mfc/mfc-desktop-applications>`_
+  <https://learn.microsoft.com/cpp/mfc/mfc-desktop-applications>`_
   (MFC) user interfaces
 
 `PythonWin <https://web.archive.org/web/20060524042422/