diff --git a/Mac/Makefile.in b/Mac/Makefile.in
index c40ad1a455a..03ec738e343 100644
--- a/Mac/Makefile.in
+++ b/Mac/Makefile.in
@@ -5,6 +5,7 @@
 VERSION=@VERSION@
 ABIFLAGS=@ABIFLAGS@
 LDVERSION=@LDVERSION@
+ENSUREPIP=@ENSUREPIP@
 builddir = ..
 srcdir=@srcdir@
 prefix=@prefix@
@@ -92,6 +93,16 @@ installunixtools:
 			$(LN) -s $(BINDIR)/$${fn} $${fn} ;\
 		done ;\
 	fi
+	-if test "x$(ENSUREPIP)" != "xno"  ; then \
+		cd "$(DESTDIR)$(FRAMEWORKUNIXTOOLSPREFIX)/bin" && \
+		for fn in \
+				pip3 \
+				; \
+		do \
+			rm -f $${fn} ;\
+			$(LN) -s $(BINDIR)/$${fn} $${fn} ;\
+		done ;\
+	fi
 
 #
 # Like installunixtools, but only install links to the versioned binaries.
@@ -133,6 +144,17 @@ altinstallunixtools:
 			$(LN) -s $(BINDIR)/$${fn} $${fn} ;\
 		done ;\
 	fi
+	-if test "x$(ENSUREPIP)" != "xno"  ; then \
+		cd "$(DESTDIR)$(FRAMEWORKUNIXTOOLSPREFIX)/bin" && \
+		for fn in \
+				easy_install-$(VERSION) \
+				pip$(VERSION) \
+				; \
+		do \
+			rm -f $${fn} ;\
+			$(LN) -s $(BINDIR)/$${fn} $${fn} ;\
+		done ;\
+	fi
 
 pythonw: $(srcdir)/Tools/pythonw.c Makefile
 	$(CC) $(LDFLAGS) -DPYTHONFRAMEWORK='"$(PYTHONFRAMEWORK)"' -o $@ \
diff --git a/Makefile.pre.in b/Makefile.pre.in
index 0e75bbece1d..0ccf755768a 100644
--- a/Makefile.pre.in
+++ b/Makefile.pre.in
@@ -160,6 +160,9 @@ OTHER_LIBTOOL_OPT=@OTHER_LIBTOOL_OPT@
 # Environment to run shared python without installed libraries
 RUNSHARED=       @RUNSHARED@
 
+# ensurepip options
+ENSUREPIP=      @ENSUREPIP@
+
 # Modes for directories, executables and data files created by the
 # install process.  Default to user-only-writable for all file types.
 DIRMODE=	755
@@ -961,10 +964,30 @@ quicktest:	all platform
 		$(TESTRUNNER) $(QUICKTESTOPTS)
 
 
-install: @FRAMEWORKINSTALLFIRST@ altinstall bininstall maninstall @FRAMEWORKINSTALLLAST@
+install: @FRAMEWORKINSTALLFIRST@ commoninstall bininstall maninstall @FRAMEWORKINSTALLLAST@
+	if test "x$(ENSUREPIP)" != "xno"  ; then \
+		case $(ENSUREPIP) in \
+			upgrade) ensurepip="--upgrade" ;; \
+			install|*) ensurepip="" ;; \
+		esac; \
+		$(RUNSHARED) $(PYTHON_FOR_BUILD) -m ensurepip \
+			$$ensurepip --root=$(DESTDIR)/ ; \
+	fi
 
-altinstall:	@FRAMEWORKALTINSTALLFIRST@ altbininstall libinstall inclinstall libainstall \
-                sharedinstall oldsharedinstall altmaninstall @FRAMEWORKALTINSTALLLAST@
+altinstall: commoninstall
+	if test "x$(ENSUREPIP)" != "xno"  ; then \
+		case $(ENSUREPIP) in \
+			upgrade) ensurepip="--altinstall --upgrade" ;; \
+			install|*) ensurepip="--altinstall" ;; \
+		esac; \
+		$(RUNSHARED) $(PYTHON_FOR_BUILD) -m ensurepip \
+			$$ensurepip --root=$(DESTDIR)/ ; \
+	fi
+
+commoninstall:  @FRAMEWORKALTINSTALLFIRST@ \
+		altbininstall libinstall inclinstall libainstall \
+		sharedinstall oldsharedinstall altmaninstall \
+		@FRAMEWORKALTINSTALLLAST@
 
 # Install shared libraries enabled by Setup
 DESTDIRS=	$(exec_prefix) $(LIBDIR) $(BINLIBDEST) $(DESTSHARED)
@@ -1570,7 +1593,7 @@ Python/thread.o: @THREADHEADERS@
 .PHONY: frameworkinstall frameworkinstallframework frameworkinstallstructure
 .PHONY: frameworkinstallmaclib frameworkinstallapps frameworkinstallunixtools
 .PHONY: frameworkaltinstallunixtools recheck autoconf clean clobber distclean
-.PHONY: smelly funny patchcheck touch altmaninstall
+.PHONY: smelly funny patchcheck touch altmaninstall commoninstall
 .PHONY: gdbhooks
 
 # IF YOU PUT ANYTHING HERE IT WILL GO AWAY
diff --git a/Misc/NEWS b/Misc/NEWS
index 6d453fec880..92d902af9cf 100644
--- a/Misc/NEWS
+++ b/Misc/NEWS
@@ -363,6 +363,12 @@ Build
   installed for 64-bit/32-bit universal builds.  The obsolete and
   undocumented pythonw* symlinks are no longer installed anywhere.
 
+- Issue #19553: PEP 453 - "make install" and "make altinstall" now install or
+  upgrade pip by default, using the bundled pip provided by the new ensurepip
+  module.  A new configure option, --with-ensurepip[=upgrade|install|no], is
+  available to override the default ensurepip "--upgrade" option.  The option
+  can also be set with "make [alt]install ENSUREPIP=[upgrade|install\no]".
+
 Tools/Demos
 -----------
 
diff --git a/configure b/configure
index b40058aea03..5d666ed93eb 100755
--- a/configure
+++ b/configure
@@ -623,6 +623,7 @@ ac_includes_default="\
 #endif"
 
 ac_subst_vars='LTLIBOBJS
+ENSUREPIP
 SRCDIRS
 THREADHEADERS
 LIBPL
@@ -815,6 +816,7 @@ with_libm
 with_libc
 enable_big_digits
 with_computed_gotos
+with_ensurepip
 '
       ac_precious_vars='build_alias
 host_alias
@@ -1498,6 +1500,8 @@ Optional Packages:
   --with(out)-computed-gotos
                           Use computed gotos in evaluation loop (enabled by
                           default on supported compilers)
+  --with(out)-ensurepip=[=upgrade]
+                          "install" or "upgrade" using bundled pip
 
 Some influential environment variables:
   MACHDEP     name for machine-dependent library files
@@ -15344,6 +15348,31 @@ $as_echo "#define HAVE_IPA_PURE_CONST_BUG 1" >>confdefs.h
     esac
 fi
 
+# ensurepip option
+{ $as_echo "$as_me:${as_lineno-$LINENO}: checking for ensurepip" >&5
+$as_echo_n "checking for ensurepip... " >&6; }
+
+# Check whether --with-ensurepip was given.
+if test "${with_ensurepip+set}" = set; then :
+  withval=$with_ensurepip;
+else
+  with_ensurepip=upgrade
+fi
+
+case $with_ensurepip in #(
+  yes|upgrade) :
+    ENSUREPIP=upgrade ;; #(
+  install) :
+    ENSUREPIP=install ;; #(
+  no) :
+    ENSUREPIP=no ;; #(
+  *) :
+    as_fn_error $? "--with-ensurepip=upgrade|install|no" "$LINENO" 5 ;;
+esac
+{ $as_echo "$as_me:${as_lineno-$LINENO}: result: $ENSUREPIP" >&5
+$as_echo "$ENSUREPIP" >&6; }
+
+
 # generate output files
 ac_config_files="$ac_config_files Makefile.pre Modules/Setup.config Misc/python.pc Misc/python-config.sh"
 
diff --git a/configure.ac b/configure.ac
index 02f481eb4ca..14b3aef6046 100644
--- a/configure.ac
+++ b/configure.ac
@@ -4767,6 +4767,21 @@ if test "$have_gcc_asm_for_x87" = yes; then
     esac
 fi
 
+# ensurepip option
+AC_MSG_CHECKING(for ensurepip)
+AC_ARG_WITH(ensurepip,
+    [AS_HELP_STRING([--with(out)-ensurepip=@<:@=upgrade@:>@],
+        ["install" or "upgrade" using bundled pip])],
+    [],
+    [with_ensurepip=upgrade])
+AS_CASE($with_ensurepip,
+    [yes|upgrade],[ENSUREPIP=upgrade],
+    [install],[ENSUREPIP=install],
+    [no],[ENSUREPIP=no],
+    [AC_MSG_ERROR([--with-ensurepip=upgrade|install|no])])
+AC_MSG_RESULT($ENSUREPIP)
+AC_SUBST(ENSUREPIP)
+
 # generate output files
 AC_CONFIG_FILES(Makefile.pre Modules/Setup.config Misc/python.pc Misc/python-config.sh)
 AC_CONFIG_FILES([Modules/ld_so_aix], [chmod +x Modules/ld_so_aix])