diff --git a/.gitignore b/.gitignore
index d9c4a7972f076d5..ef7642b09bc5d2a 100644
--- a/.gitignore
+++ b/.gitignore
@@ -23,6 +23,10 @@
 *.gc??
 *.profclang?
 *.profraw
+# Copies of binaries before BOLT optimizations.
+*.prebolt
+# BOLT profile data.
+*.fdata
 *.dyn
 .gdb_history
 .purify
@@ -124,6 +128,7 @@ Tools/unicode/data/
 /platform
 /profile-clean-stamp
 /profile-run-stamp
+/profile-bolt-stamp
 /Python/deepfreeze/*.c
 /pybuilddir.txt
 /pyconfig.h
diff --git a/Makefile.pre.in b/Makefile.pre.in
index da3a8f6c13f90b3..eb79c9c4ca18016 100644
--- a/Makefile.pre.in
+++ b/Makefile.pre.in
@@ -672,21 +672,55 @@ profile-opt: profile-run-stamp
 	-rm -f profile-clean-stamp
 	$(MAKE) @DEF_MAKE_RULE@ CFLAGS_NODIST="$(CFLAGS_NODIST) $(PGO_PROF_USE_FLAG)" LDFLAGS_NODIST="$(LDFLAGS_NODIST)"
 
-.PHONY: bolt-opt
-bolt-opt: @PREBOLT_RULE@
+# List of binaries that BOLT runs on.
+BOLT_BINARIES := @BOLT_BINARIES@
+
+BOLT_INSTRUMENT_FLAGS := @BOLT_INSTRUMENT_FLAGS@
+BOLT_APPLY_FLAGS := @BOLT_APPLY_FLAGS@
+
+.PHONY: clean-bolt
+clean-bolt:
+	# Profile data.
 	rm -f *.fdata
-	@if $(READELF) -p .note.bolt_info $(BUILDPYTHON) | grep BOLT > /dev/null; then\
-		echo "skip: $(BUILDPYTHON) is already BOLTed."; \
-	else \
-		@LLVM_BOLT@ ./$(BUILDPYTHON) -instrument -instrumentation-file-append-pid -instrumentation-file=$(abspath $(BUILDPYTHON).bolt) -o $(BUILDPYTHON).bolt_inst; \
-		./$(BUILDPYTHON).bolt_inst $(PROFILE_TASK) || true; \
-		@MERGE_FDATA@ $(BUILDPYTHON).*.fdata > $(BUILDPYTHON).fdata; \
-		@LLVM_BOLT@ ./$(BUILDPYTHON) -o $(BUILDPYTHON).bolt -data=$(BUILDPYTHON).fdata -update-debug-sections -reorder-blocks=ext-tsp -reorder-functions=hfsort+ -split-functions -icf=1 -inline-all -split-eh -reorder-functions-use-hot-size -peepholes=none -jump-tables=aggressive -inline-ap -indirect-call-promotion=all -dyno-stats -use-gnu-stack -frame-opt=hot; \
-		rm -f *.fdata; \
-		rm -f $(BUILDPYTHON).bolt_inst; \
-		mv $(BUILDPYTHON).bolt $(BUILDPYTHON); \
-	fi
+	# Pristine binaries before BOLT optimization.
+	rm -f *.prebolt
+	# BOLT instrumented binaries.
+	rm -f *.bolt_inst
+
+profile-bolt-stamp: $(BUILDPYTHON)
+	# Ensure a pristine, pre-BOLT copy of the binary and no profile data from last run.
+	for bin in $(BOLT_BINARIES); do \
+	  prebolt="$${bin}.prebolt"; \
+	  if [ -e "$${prebolt}" ]; then \
+	    echo "Restoring pre-BOLT binary $${prebolt}"; \
+	    mv "$${bin}.prebolt" "$${bin}"; \
+	  fi; \
+	  cp "$${bin}" "$${prebolt}"; \
+	  rm -f $${bin}.bolt.*.fdata $${bin}.fdata; \
+	done
+	# Instrument each binary.
+	for bin in $(BOLT_BINARIES); do \
+	  @LLVM_BOLT@ "$${bin}" -instrument -instrumentation-file-append-pid -instrumentation-file=$(abspath $${bin}.bolt) -o $${bin}.bolt_inst $(BOLT_INSTRUMENT_FLAGS); \
+	  mv "$${bin}.bolt_inst" "$${bin}"; \
+	done
+	# Run instrumented binaries to collect data.
+	$(RUNSHARED) ./$(BUILDPYTHON) $(PROFILE_TASK) || true
+	# Merge all the data files together.
+	for bin in $(BOLT_BINARIES); do \
+	  @MERGE_FDATA@ $${bin}.*.fdata > "$${bin}.fdata"; \
+	  rm -f $${bin}.*.fdata; \
+	done
+	# Run bolt against the merged data to produce an optimized binary.
+	for bin in $(BOLT_BINARIES); do \
+	  @LLVM_BOLT@ "$${bin}.prebolt" -o "$${bin}.bolt" -data="$${bin}.fdata" $(BOLT_APPLY_FLAGS); \
+	  mv "$${bin}.bolt" "$${bin}"; \
+	done
+	touch $@
 
+.PHONY: bolt-opt
+bolt-opt:
+	$(MAKE) @PREBOLT_RULE@
+	$(MAKE) profile-bolt-stamp
 
 # Compile and run with gcov
 .PHONY: coverage
@@ -2623,10 +2657,11 @@ profile-removal:
 	rm -f $(COVERAGE_INFO)
 	rm -rf $(COVERAGE_REPORT)
 	rm -f profile-run-stamp
+	rm -f profile-bolt-stamp
 
 .PHONY: clean
-clean: clean-retain-profile
-	@if test @DEF_MAKE_ALL_RULE@ = profile-opt; then \
+clean: clean-retain-profile clean-bolt
+	@if test @DEF_MAKE_ALL_RULE@ = profile-opt -o @DEF_MAKE_ALL_RULE@ = bolt-opt; then \
 		rm -f profile-gen-stamp profile-clean-stamp; \
 		$(MAKE) profile-removal; \
 	fi
diff --git a/Misc/NEWS.d/next/Build/2023-05-20-16-09-59.gh-issue-101282.FvRARb.rst b/Misc/NEWS.d/next/Build/2023-05-20-16-09-59.gh-issue-101282.FvRARb.rst
new file mode 100644
index 000000000000000..cc70d47c6c16dd9
--- /dev/null
+++ b/Misc/NEWS.d/next/Build/2023-05-20-16-09-59.gh-issue-101282.FvRARb.rst
@@ -0,0 +1,4 @@
+BOLT optimization is now applied to the libpython shared library if building
+a shared library. BOLT instrumentation and application settings can now be
+influenced via the ``BOLT_INSTRUMENT_FLAGS`` and ``BOLT_APPLY_FLAGS``
+configure variables.
diff --git a/configure b/configure
index 7aad4fe89e3cbf2..790a92856da8629 100755
--- a/configure
+++ b/configure
@@ -883,10 +883,11 @@ CFLAGS_NODIST
 BASECFLAGS
 CFLAGS_ALIASING
 OPT
+BOLT_APPLY_FLAGS
+BOLT_INSTRUMENT_FLAGS
+BOLT_BINARIES
 MERGE_FDATA
 LLVM_BOLT
-ac_ct_READELF
-READELF
 PREBOLT_RULE
 LLVM_PROF_FOUND
 LLVM_PROFDATA
@@ -1105,6 +1106,8 @@ CPPFLAGS
 CPP
 HOSTRUNNER
 PROFILE_TASK
+BOLT_INSTRUMENT_FLAGS
+BOLT_APPLY_FLAGS
 LIBUUID_CFLAGS
 LIBUUID_LIBS
 LIBFFI_CFLAGS
@@ -1916,6 +1919,10 @@ Some influential environment variables:
   HOSTRUNNER  Program to run CPython for the host platform
   PROFILE_TASK
               Python args for PGO generation task
+  BOLT_INSTRUMENT_FLAGS
+              Arguments to llvm-bolt when instrumenting binaries
+  BOLT_APPLY_FLAGS
+              Arguments to llvm-bolt when creating a BOLT optimized binary
   LIBUUID_CFLAGS
               C compiler flags for LIBUUID, overriding pkg-config
   LIBUUID_LIBS
@@ -8106,112 +8113,6 @@ if test "$Py_BOLT" = 'true' ; then
   DEF_MAKE_ALL_RULE="bolt-opt"
   DEF_MAKE_RULE="build_all"
 
-
-  if test -n "$ac_tool_prefix"; then
-  for ac_prog in readelf
-  do
-    # Extract the first word of "$ac_tool_prefix$ac_prog", so it can be a program name with args.
-set dummy $ac_tool_prefix$ac_prog; ac_word=$2
-{ $as_echo "$as_me:${as_lineno-$LINENO}: checking for $ac_word" >&5
-$as_echo_n "checking for $ac_word... " >&6; }
-if ${ac_cv_prog_READELF+:} false; then :
-  $as_echo_n "(cached) " >&6
-else
-  if test -n "$READELF"; then
-  ac_cv_prog_READELF="$READELF" # Let the user override the test.
-else
-as_save_IFS=$IFS; IFS=$PATH_SEPARATOR
-for as_dir in $PATH
-do
-  IFS=$as_save_IFS
-  test -z "$as_dir" && as_dir=.
-    for ac_exec_ext in '' $ac_executable_extensions; do
-  if as_fn_executable_p "$as_dir/$ac_word$ac_exec_ext"; then
-    ac_cv_prog_READELF="$ac_tool_prefix$ac_prog"
-    $as_echo "$as_me:${as_lineno-$LINENO}: found $as_dir/$ac_word$ac_exec_ext" >&5
-    break 2
-  fi
-done
-  done
-IFS=$as_save_IFS
-
-fi
-fi
-READELF=$ac_cv_prog_READELF
-if test -n "$READELF"; then
-  { $as_echo "$as_me:${as_lineno-$LINENO}: result: $READELF" >&5
-$as_echo "$READELF" >&6; }
-else
-  { $as_echo "$as_me:${as_lineno-$LINENO}: result: no" >&5
-$as_echo "no" >&6; }
-fi
-
-
-    test -n "$READELF" && break
-  done
-fi
-if test -z "$READELF"; then
-  ac_ct_READELF=$READELF
-  for ac_prog in readelf
-do
-  # Extract the first word of "$ac_prog", so it can be a program name with args.
-set dummy $ac_prog; ac_word=$2
-{ $as_echo "$as_me:${as_lineno-$LINENO}: checking for $ac_word" >&5
-$as_echo_n "checking for $ac_word... " >&6; }
-if ${ac_cv_prog_ac_ct_READELF+:} false; then :
-  $as_echo_n "(cached) " >&6
-else
-  if test -n "$ac_ct_READELF"; then
-  ac_cv_prog_ac_ct_READELF="$ac_ct_READELF" # Let the user override the test.
-else
-as_save_IFS=$IFS; IFS=$PATH_SEPARATOR
-for as_dir in $PATH
-do
-  IFS=$as_save_IFS
-  test -z "$as_dir" && as_dir=.
-    for ac_exec_ext in '' $ac_executable_extensions; do
-  if as_fn_executable_p "$as_dir/$ac_word$ac_exec_ext"; then
-    ac_cv_prog_ac_ct_READELF="$ac_prog"
-    $as_echo "$as_me:${as_lineno-$LINENO}: found $as_dir/$ac_word$ac_exec_ext" >&5
-    break 2
-  fi
-done
-  done
-IFS=$as_save_IFS
-
-fi
-fi
-ac_ct_READELF=$ac_cv_prog_ac_ct_READELF
-if test -n "$ac_ct_READELF"; then
-  { $as_echo "$as_me:${as_lineno-$LINENO}: result: $ac_ct_READELF" >&5
-$as_echo "$ac_ct_READELF" >&6; }
-else
-  { $as_echo "$as_me:${as_lineno-$LINENO}: result: no" >&5
-$as_echo "no" >&6; }
-fi
-
-
-  test -n "$ac_ct_READELF" && break
-done
-
-  if test "x$ac_ct_READELF" = x; then
-    READELF=""notfound""
-  else
-    case $cross_compiling:$ac_tool_warned in
-yes:)
-{ $as_echo "$as_me:${as_lineno-$LINENO}: WARNING: using cross tools not prefixed with host triplet" >&5
-$as_echo "$as_me: WARNING: using cross tools not prefixed with host triplet" >&2;}
-ac_tool_warned=yes ;;
-esac
-    READELF=$ac_ct_READELF
-  fi
-fi
-
-  if test "$READELF" == "notfound"
-  then
-    as_fn_error $? "readelf is required for a --enable-bolt build but could not be found." "$LINENO" 5
-  fi
-
   # -fno-reorder-blocks-and-partition is required for bolt to work.
   # Possibly GCC only.
   { $as_echo "$as_me:${as_lineno-$LINENO}: checking whether C compiler accepts -fno-reorder-blocks-and-partition" >&5
@@ -8474,6 +8375,34 @@ $as_echo "\"Found merge-fdata\"" >&6; }
   fi
 fi
 
+# Enable BOLT of libpython if built.
+
+BOLT_BINARIES='$(BUILDPYTHON)'
+if test "${enable_shared}" = "yes"
+then
+  BOLT_BINARIES="${BOLT_BINARIES} \$(INSTSONAME)"
+fi
+
+
+{ $as_echo "$as_me:${as_lineno-$LINENO}: checking BOLT_INSTRUMENT_FLAGS" >&5
+$as_echo_n "checking BOLT_INSTRUMENT_FLAGS... " >&6; }
+if test -z "${BOLT_INSTRUMENT_FLAGS}"
+then
+  BOLT_INSTRUMENT_FLAGS=
+fi
+{ $as_echo "$as_me:${as_lineno-$LINENO}: result: $BOLT_INSTRUMENT_FLAGS" >&5
+$as_echo "$BOLT_INSTRUMENT_FLAGS" >&6; }
+
+
+{ $as_echo "$as_me:${as_lineno-$LINENO}: checking BOLT_APPLY_FLAGS" >&5
+$as_echo_n "checking BOLT_APPLY_FLAGS... " >&6; }
+if test -z "${BOLT_APPLY_FLAGS}"
+then
+  BOLT_APPLY_FLAGS="-update-debug-sections -reorder-blocks=ext-tsp -reorder-functions=hfsort+ -split-functions -icf=1 -inline-all -split-eh -reorder-functions-use-hot-size -peepholes=none -jump-tables=aggressive -inline-ap -indirect-call-promotion=all -dyno-stats -use-gnu-stack -frame-opt=hot"
+fi
+{ $as_echo "$as_me:${as_lineno-$LINENO}: result: $BOLT_APPLY_FLAGS" >&5
+$as_echo "$BOLT_APPLY_FLAGS" >&6; }
+
 # XXX Shouldn't the code above that fiddles with BASECFLAGS and OPT be
 # merged with this chunk of code?
 
diff --git a/configure.ac b/configure.ac
index 115998e0753b264..2ef3bbae388d389 100644
--- a/configure.ac
+++ b/configure.ac
@@ -2028,13 +2028,6 @@ if test "$Py_BOLT" = 'true' ; then
   DEF_MAKE_ALL_RULE="bolt-opt"
   DEF_MAKE_RULE="build_all"
 
-  AC_SUBST(READELF)
-  AC_CHECK_TOOLS(READELF, [readelf], "notfound")
-  if test "$READELF" == "notfound"
-  then
-    AC_MSG_ERROR([readelf is required for a --enable-bolt build but could not be found.])
-  fi
-
   # -fno-reorder-blocks-and-partition is required for bolt to work.
   # Possibly GCC only.
   AX_CHECK_COMPILE_FLAG([-fno-reorder-blocks-and-partition],[
@@ -2067,6 +2060,30 @@ if test "$Py_BOLT" = 'true' ; then
   fi
 fi
 
+# Enable BOLT of libpython if built.
+AC_SUBST(BOLT_BINARIES)
+BOLT_BINARIES='$(BUILDPYTHON)'
+if test "${enable_shared}" = "yes"
+then
+  BOLT_BINARIES="${BOLT_BINARIES} \$(INSTSONAME)"
+fi
+
+AC_ARG_VAR(BOLT_INSTRUMENT_FLAGS, Arguments to llvm-bolt when instrumenting binaries)
+AC_MSG_CHECKING(BOLT_INSTRUMENT_FLAGS)
+if test -z "${BOLT_INSTRUMENT_FLAGS}"
+then
+  BOLT_INSTRUMENT_FLAGS=
+fi
+AC_MSG_RESULT($BOLT_INSTRUMENT_FLAGS)
+
+AC_ARG_VAR(BOLT_APPLY_FLAGS, Arguments to llvm-bolt when creating a BOLT optimized binary)
+AC_MSG_CHECKING(BOLT_APPLY_FLAGS)
+if test -z "${BOLT_APPLY_FLAGS}"
+then
+  BOLT_APPLY_FLAGS="-update-debug-sections -reorder-blocks=ext-tsp -reorder-functions=hfsort+ -split-functions -icf=1 -inline-all -split-eh -reorder-functions-use-hot-size -peepholes=none -jump-tables=aggressive -inline-ap -indirect-call-promotion=all -dyno-stats -use-gnu-stack -frame-opt=hot"
+fi
+AC_MSG_RESULT($BOLT_APPLY_FLAGS)
+
 # XXX Shouldn't the code above that fiddles with BASECFLAGS and OPT be
 # merged with this chunk of code?