diff --git a/autoconf/Dockerfile b/autoconf/Dockerfile
index da9abba..9e809fb 100644
--- a/autoconf/Dockerfile
+++ b/autoconf/Dockerfile
@@ -3,6 +3,9 @@ FROM docker.io/library/ubuntu:24.04
 ARG AUTOCONF_VERSION="2.72"
 ARG AUTOCONF_ARCHIVE_VERSION="2023.02.20"
 ARG AUTOMAKE_VERSION="1.16.5"
+# Specific revision of https://git.savannah.gnu.org/git/config.git
+# for config.guess and config.sub.
+ARG CONFIG_GIT_REV="00b15927496058d23e6258a28d8996f87cf1f191"
 
 LABEL org.opencontainers.image.source="https://github.com/python/cpython-devcontainers"
 LABEL org.opencontainers.image.base.name="docker.io/library/ubuntu:22.04"
@@ -40,6 +43,15 @@ RUN PATCH_VERBOSE=1 curl https://ftp.gnu.org/gnu/autoconf-archive/autoconf-archi
     && ./configure --prefix=/usr/local \
     && make \
     && make install
+ADD --chmod=755 https://git.savannah.gnu.org/gitweb/?p=config.git;a=blob_plain;f=config.guess;hb=${CONFIG_GIT_REV} \
+    /usr/local/share/autoconf/build-aux/config.guess
+ADD --chmod=755 https://git.savannah.gnu.org/gitweb/?p=config.git;a=blob_plain;f=config.sub;hb=${CONFIG_GIT_REV} \
+    /usr/local/share/autoconf/build-aux/config.sub
+COPY config.sub.patch .
+RUN p=$(pwd)/config.sub.patch \
+    && cd /usr/local/share/autoconf/build-aux \
+    && patch -p1 <$p \
+    && rm "$p"
 
 # https://stackoverflow.com/questions/8811381/possibly-undefined-macro-ac-msg-error/49103418#49103418
 RUN cp /usr/local/share/aclocal/*.m4 /usr/share/aclocal \
diff --git a/autoconf/config.sub.patch b/autoconf/config.sub.patch
new file mode 100644
index 0000000..3cbd448
--- /dev/null
+++ b/autoconf/config.sub.patch
@@ -0,0 +1,64 @@
+From 7a7c6fc48512405ede8b2db440b702e866364b00 Mon Sep 17 00:00:00 2001
+From: Russell Keith-Magee <russell@keith-magee.com>
+Date: Mon, 26 Feb 2024 09:21:10 +0800
+Subject: [PATCH] config.sub: Include support for arm64_32 and iOS/tvOS/watchOS
+ simulators
+
+  * Normalise the watchOS CPU architecture descriptor used by
+    Apple (`arm64_32`).
+  * Accept the `-simulator` suffix for descriptors for iOS, tvOS and
+    watchOS.
+
+The following is the list of compiler triples generated by Apple's
+clang toolchains for iOS 12.0, tvOS 9.0, and watchOS 4.0:
+
+  * `arm64-apple-ios12.0`
+  * `x86_64-apple-ios12.0-simulator`
+  * `arm64-apple-ios12.0-simulator`
+  * `arm64-apple-tvos9.0`
+  * `x86_64-apple-tvos9.0-simulator`
+  * `arm64-apple-tvos9.0-simulator`
+  * `arm64_32-apple-watchos4.0`
+  * `arm64-apple-watchos4.0-simulator`
+
+The `-simulator` suffix is significant because iOS devices and iOS
+simulators have a different ABI.  It is therefore essential that these
+can be differentiated in a compiler triple.
+---
+ config.sub | 6 ++++--
+ 1 file changed, 4 insertions(+), 2 deletions(-)
+
+diff --git a/config.sub b/config.sub
+index 4aaae46..335706d 100755
+--- a/config.sub
++++ b/config.sub
+@@ -4,7 +4,7 @@
+ 
+ # shellcheck disable=SC2006,SC2268,SC2162 # see below for rationale
+ 
+-timestamp='2024-05-27'
++timestamp='2025-01-06'
+ 
+ # This file is free software; you can redistribute it and/or modify it
+ # under the terms of the GNU General Public License as published by
+@@ -1194,7 +1194,7 @@ case $cpu-$vendor in
+ 	xscale-* | xscalee[bl]-*)
+ 		cpu=`echo "$cpu" | sed 's/^xscale/arm/'`
+ 		;;
+-	arm64-* | aarch64le-*)
++	arm64-* | aarch64le-* | arm64_32-*)
+ 		cpu=aarch64
+ 		;;
+ 
+@@ -2249,6 +2249,8 @@ case $kernel-$os-$obj in
+ 		;;
+ 	*-eabi*- | *-gnueabi*-)
+ 		;;
++	ios*-simulator- | tvos*-simulator- | watchos*-simulator- )
++		;;
+ 	none--*)
+ 		# None (no kernel, i.e. freestanding / bare metal),
+ 		# can be paired with an machine code file format
+-- 
+2.47.1
+
diff --git a/autoconf/entry.sh b/autoconf/entry.sh
index 5075608..d73b08c 100755
--- a/autoconf/entry.sh
+++ b/autoconf/entry.sh
@@ -22,6 +22,14 @@ if [ "$#" = "0" ]; then
     fi
 
     echo "Rebuilding configure script using $($AUTOCONF --version | head -n 1)"
+    set -x
+    # autoreconf's '--force' option doesn't affect any of the files installed
+    # by the '--install' option.  Remove the files to truly force them to be
+    # updated so that the CPython repo doesn't drift from this repo.
+    rm -f /src/aclocal.m4
+    rm -f /src/config.guess
+    rm -f /src/config.sub
+    rm -f /src/install-sh
     exec $AUTORECONF -ivf -Werror $@
 fi