diff --git a/Doc/faq/gui.rst b/Doc/faq/gui.rst
index 4f9979bf55e..781da467d18 100644
--- a/Doc/faq/gui.rst
+++ b/Doc/faq/gui.rst
@@ -104,7 +104,7 @@ What platform-specific GUI toolkits exist for Python?
 ========================================================
 
 By installing the `PyObjc Objective-C bridge
-<https://pythonhosted.org/pyobjc/>`_, Python programs can use Mac OS X's
+<https://pypi.org/project/pyobjc/>`_, Python programs can use Mac OS X's
 Cocoa libraries.
 
 :ref:`Pythonwin <windows-faq>` by Mark Hammond includes an interface to the
diff --git a/Doc/library/readline.rst b/Doc/library/readline.rst
index 16c28cf7d02..eae0a6df45f 100644
--- a/Doc/library/readline.rst
+++ b/Doc/library/readline.rst
@@ -19,7 +19,7 @@ function.
 
 Readline keybindings may be configured via an initialization file, typically
 ``.inputrc`` in your home directory.  See `Readline Init File
-<https://cnswww.cns.cwru.edu/php/chet/readline/rluserman.html#SEC9>`_
+<https://tiswww.cwru.edu/php/chet/readline/rluserman.html#SEC9>`_
 in the GNU Readline manual for information about the format and
 allowable constructs of that file, and the capabilities of the
 Readline library in general.
diff --git a/Doc/library/tkinter.rst b/Doc/library/tkinter.rst
index 60cf892e088..640fb2ec61d 100644
--- a/Doc/library/tkinter.rst
+++ b/Doc/library/tkinter.rst
@@ -55,7 +55,7 @@ installed, so you can read the Tcl/Tk documentation specific to that version.
    `Tcl/Tk recent man pages <https://www.tcl.tk/doc/>`_
       Recent Tcl/Tk manuals on www.tcl.tk.
 
-   `ActiveState Tcl Home Page <http://tcl.activestate.com/>`_
+   `ActiveState Tcl Home Page <https://tcl.tk>`_
       The Tk/Tcl development is largely taking place at ActiveState.
 
    `Tcl and the Tk Toolkit <https://www.amazon.com/exec/obidos/ASIN/020163337X>`_
diff --git a/Doc/using/mac.rst b/Doc/using/mac.rst
index a386728eaee..bc022fa58c0 100644
--- a/Doc/using/mac.rst
+++ b/Doc/using/mac.rst
@@ -141,7 +141,7 @@ There are several options for building GUI applications on the Mac with Python.
 
 *PyObjC* is a Python binding to Apple's Objective-C/Cocoa framework, which is
 the foundation of most modern Mac development. Information on PyObjC is
-available from https://pythonhosted.org/pyobjc/.
+available from https://pypi.org/project/pyobjc/.
 
 The standard Python GUI toolkit is :mod:`tkinter`, based on the cross-platform
 Tk toolkit (https://www.tcl.tk). An Aqua-native version of Tk is bundled with OS
diff --git a/Doc/using/windows.rst b/Doc/using/windows.rst
index 44b646fddfc..a1b25ffd25f 100644
--- a/Doc/using/windows.rst
+++ b/Doc/using/windows.rst
@@ -1043,7 +1043,9 @@ The `PyWin32 <https://pypi.org/project/pywin32>`_ module by Mark Hammond
 is a collection of modules for advanced Windows-specific support.  This includes
 utilities for:
 
-* `Component Object Model <https://www.microsoft.com/com/>`_ (COM)
+* `Component Object Model
+  <https://docs.microsoft.com/en-us/windows/desktop/com/component-object-model--com--portal>`_
+  (COM)
 * Win32 API calls
 * Registry
 * Event log
@@ -1109,8 +1111,7 @@ For extension modules, consult :ref:`building-on-windows`.
       MinGW gcc under Windows" or "Installing Python extension with distutils
       and without Microsoft Visual C++" by Sébastien Sauvage, 2003
 
-   `MingW -- Python extensions <http://oldwiki.mingw.org/index.php/Python%20extensions>`_
-      by Trent Apted et al, 2007
+   `MingW -- Python extensions <http://www.mingw.org/wiki/FAQ#toc14>`_
 
 
 Other Platforms
diff --git a/Doc/whatsnew/2.6.rst b/Doc/whatsnew/2.6.rst
index 512b8edb357..b6174a19a17 100644
--- a/Doc/whatsnew/2.6.rst
+++ b/Doc/whatsnew/2.6.rst
@@ -227,7 +227,7 @@ the Python community.
 
 Sphinx is a standalone package that can be used for writing, and
 almost two dozen other projects
-(`listed on the Sphinx web site <http://sphinx-doc.org/examples.html>`__)
+(`listed on the Sphinx web site <https://www.sphinx-doc.org/en/master/examples.html>`__)
 have adopted Sphinx as their documentation tool.
 
 .. seealso::
diff --git a/Doc/whatsnew/3.2.rst b/Doc/whatsnew/3.2.rst
index 2d740006a37..ca3eda05c51 100644
--- a/Doc/whatsnew/3.2.rst
+++ b/Doc/whatsnew/3.2.rst
@@ -50,7 +50,9 @@
 
 This article explains the new features in Python 3.2 as compared to 3.1.  It
 focuses on a few highlights and gives a few examples.  For full details, see the
-`Misc/NEWS <https://hg.python.org/cpython/file/3.2/Misc/NEWS>`_ file.
+`Misc/NEWS
+<https://github.com/python/cpython/blob/076ca6c3c8df3030307e548d9be792ce3c1c6eea/Misc/NEWS>`_
+file.
 
 .. seealso::
 
@@ -969,10 +971,10 @@ sites do not finish before midnight, the barrier times-out and the ballots are
 sealed and deposited in a queue for later handling.
 
 See `Barrier Synchronization Patterns
-<https://parlab.eecs.berkeley.edu/wiki/_media/patterns/paraplop_g1_3.pdf>`_ for
-more examples of how barriers can be used in parallel computing.  Also, there is
+<http://osl.cs.illinois.edu/media/papers/karmani-2009-barrier_synchronization_pattern.pdf>`_
+for more examples of how barriers can be used in parallel computing.  Also, there is
 a simple but thorough explanation of barriers in `The Little Book of Semaphores
-<http://greenteapress.com/semaphores/downey08semaphores.pdf>`_, *section 3.6*.
+<https://greenteapress.com/semaphores/LittleBookOfSemaphores.pdf>`_, *section 3.6*.
 
 (Contributed by Kristján Valur Jónsson with an API review by Jeffrey Yasskin in
 :issue:`8777`.)
@@ -2512,9 +2514,9 @@ repository.  This distributed version control system should make it easier for
 members of the community to create and share external changesets.  See
 :pep:`385` for details.
 
-To learn to use the new version control system, see the `tutorial by Joel
-Spolsky <http://hginit.com>`_ or the `Guide to Mercurial Workflows
-<https://www.mercurial-scm.org/guide>`_.
+To learn to use the new version control system, see the `Quick Start
+<https://www.mercurial-scm.org/wiki/QuickStart>`_ or the `Guide to
+Mercurial Workflows <https://www.mercurial-scm.org/guide>`_.
 
 
 Build and C API Changes