diff --git a/Misc/NEWS b/Misc/NEWS
index 0e5d5f1cd78..7c6c158fc7d 100644
--- a/Misc/NEWS
+++ b/Misc/NEWS
@@ -555,6 +555,8 @@ Windows
 Build
 -----
 
+- Issue #26359: Rename --with-optimiations to --enable-optimizations.
+
 - Issue #28444: Fix missing extensions modules when cross compiling.
 
 - Issue #28248: Update Windows build and OS X installers to use OpenSSL 1.0.2j.
diff --git a/configure b/configure
index 19fcbd128be..179c1982aa1 100755
--- a/configure
+++ b/configure
@@ -815,7 +815,7 @@ with_suffix
 enable_shared
 enable_profiling
 with_pydebug
-with_optimizations
+enable_optimizations
 with_lto
 with_hash_algorithm
 with_address_sanitizer
@@ -1486,6 +1486,8 @@ Optional Features:
                           Build (MacOSX|Darwin) framework
   --enable-shared         disable/enable building shared python library
   --enable-profiling      enable C-level code profiling
+  --enable-optimizations  Enable expensive optimizations (PGO, maybe LTO,
+                          etc). Disabled by default.
   --enable-loadable-sqlite-extensions
                           support loadable extensions in _sqlite module
   --enable-ipv6           Enable ipv6 (with ipv4) support
@@ -1509,8 +1511,6 @@ Optional Packages:
                           compiler
   --with-suffix=.exe      set executable suffix
   --with-pydebug          build with Py_DEBUG defined
-  --with-optimizations    Enable expensive optimizations (PGO, maybe LTO,
-                          etc). Disabled by default.
   --with-lto              Enable Link Time Optimization in PGO builds.
                           Disabled by default.
   --with-hash-algorithm=[fnv|siphash24]
@@ -6543,12 +6543,11 @@ fi
 
 
 Py_OPT='false'
-{ $as_echo "$as_me:${as_lineno-$LINENO}: checking for --with-optimizations" >&5
-$as_echo_n "checking for --with-optimizations... " >&6; }
-
-# Check whether --with-optimizations was given.
-if test "${with_optimizations+set}" = set; then :
-  withval=$with_optimizations;
+{ $as_echo "$as_me:${as_lineno-$LINENO}: checking for --enable-optimizations" >&5
+$as_echo_n "checking for --enable-optimizations... " >&6; }
+# Check whether --enable-optimizations was given.
+if test "${enable_optimizations+set}" = set; then :
+  enableval=$enable_optimizations;
 if test "$withval" != no
 then
   Py_OPT='true'
@@ -6808,7 +6807,7 @@ case $CC in
       LLVM_PROF_ERR=yes
       if test "${REQUIRE_PGO}" = "yes"
       then
-        as_fn_error $? "llvm-profdata is required for a --with-optimizations build but could not be found." "$LINENO" 5
+        as_fn_error $? "llvm-profdata is required for a --enable-optimizations build but could not be found." "$LINENO" 5
       fi
     fi
     ;;
@@ -6824,7 +6823,7 @@ case $CC in
           LLVM_PROF_ERR=yes
           if test "${REQUIRE_PGO}" = "yes"
 	  then
-	    as_fn_error $? "llvm-profdata is required for a --with-optimizations build but could not be found." "$LINENO" 5
+	    as_fn_error $? "llvm-profdata is required for a --enable-optimizations build but could not be found." "$LINENO" 5
 	  fi
         fi
         ;;
@@ -17829,7 +17828,7 @@ if test "$Py_OPT" = 'false' -a "$Py_DEBUG" != 'true'; then
     echo "" >&6
     echo "" >&6
     echo "If you want a release build with all optimizations active (LTO, PGO, etc),"
-    echo "please run ./configure --with-optimizations" >&6
+    echo "please run ./configure --enable-optimizations" >&6
     echo "" >&6
     echo "" >&6
 fi
diff --git a/configure.ac b/configure.ac
index 381bab05236..4e558717724 100644
--- a/configure.ac
+++ b/configure.ac
@@ -1234,8 +1234,8 @@ fi],
 AC_SUBST(DEF_MAKE_ALL_RULE)
 AC_SUBST(DEF_MAKE_RULE)
 Py_OPT='false'
-AC_MSG_CHECKING(for --with-optimizations)
-AC_ARG_WITH(optimizations, AS_HELP_STRING([--with-optimizations], [Enable expensive optimizations (PGO, maybe LTO, etc).  Disabled by default.]),
+AC_MSG_CHECKING(for --enable-optimizations)
+AC_ARG_ENABLE(optimizations, AS_HELP_STRING([--enable-optimizations], [Enable expensive optimizations (PGO, maybe LTO, etc).  Disabled by default.]),
 [
 if test "$withval" != no
 then
@@ -1351,7 +1351,7 @@ case $CC in
       LLVM_PROF_ERR=yes
       if test "${REQUIRE_PGO}" = "yes"
       then
-        AC_MSG_ERROR([llvm-profdata is required for a --with-optimizations build but could not be found.])
+        AC_MSG_ERROR([llvm-profdata is required for a --enable-optimizations build but could not be found.])
       fi
     fi
     ;;
@@ -1367,7 +1367,7 @@ case $CC in
           LLVM_PROF_ERR=yes
           if test "${REQUIRE_PGO}" = "yes"
 	  then
-	    AC_MSG_ERROR([llvm-profdata is required for a --with-optimizations build but could not be found.])
+	    AC_MSG_ERROR([llvm-profdata is required for a --enable-optimizations build but could not be found.])
 	  fi
         fi
         ;;
@@ -5379,7 +5379,7 @@ if test "$Py_OPT" = 'false' -a "$Py_DEBUG" != 'true'; then
     echo "" >&AS_MESSAGE_FD
     echo "" >&AS_MESSAGE_FD
     echo "If you want a release build with all optimizations active (LTO, PGO, etc),"
-    echo "please run ./configure --with-optimizations" >&AS_MESSAGE_FD
+    echo "please run ./configure --enable-optimizations" >&AS_MESSAGE_FD
     echo "" >&AS_MESSAGE_FD
     echo "" >&AS_MESSAGE_FD
 fi