diff --git a/plugins/python-build/bin/python-build b/plugins/python-build/bin/python-build
index bd0c9b5f..d6a77ed5 100755
--- a/plugins/python-build/bin/python-build
+++ b/plugins/python-build/bin/python-build
@@ -1880,26 +1880,24 @@ use_macports_zlib() {
 
 use_homebrew_tcltk() {
   can_use_homebrew || return 1
+  local tcltk_formula
   # Since https://github.com/Homebrew/homebrew-core/commit/f10e88617b41555193c22fdcba6109fe82155ee2 (10.11.2024),
-  # tcl-tk is 9.0 which is not compatible with CPython as of this writing
-  # but we'll keep it as backup for cases like non-updated Homebrew
-  local tcltk
-  for tcltk in ${PYTHON_BUILD_TCLTK_FORMULA:-tcl-tk@8 tcl-tk}; do
-    local tcltk_libdir="$(brew --prefix "${tcltk}" 2>/dev/null || true)"
-    if [ -d "$tcltk_libdir" ]; then
-      echo "python-build: use tcl-tk from homebrew"
-      local tcltk_version="$(sh -c '. '"$tcltk_libdir"'/lib/tclConfig.sh; echo $TCL_VERSION')"
-      local tcltk_includes tcltk_libs
+  # tcl-tk is 9.0. It's supported in CPython since 3.14.0a1 (gh-124111) but is not officially supported as of 3.14.0
+  # so we prefer 8
+  for tcltk_formula in ${PYTHON_BUILD_TCLTK_FORMULA:-tcl-tk@8 tcl-tk}; do
+    local tcltk_prefix="$(brew --prefix "${tcltk_formula}" 2>/dev/null || true)"
+    if [ -d "$tcltk_prefix" ]; then
+      echo "python-build: use ${tcltk_formula} from homebrew"
       # In Homebrew Tcl/Tk 8.6.13, headers have been moved to the 'tcl-tk' subdir.
-      # We're not using tclConfig.sh here 'cuz it produces the version-specific path to <brew prefix>/Cellar
-      # and we'd rather have rpath set to <brew prefix>/opt/<...> to allow micro release upgrades without rebuilding
-      # XXX: do use tclConfig.sh and translate the paths if more shenanigans appear in later releases
-      if [ -d "$tcltk_libdir/include/tcl-tk" ]; then
-        tcltk_includes="-I$tcltk_libdir/include/tcl-tk"
-      else
-        tcltk_includes="-I$tcltk_libdir/include"
+      local tcltk_includes="$(sh -c 'cd '"$tcltk_prefix"'/lib; . ./tclConfig.sh; . ./tkConfig.sh; echo "$TCL_INCLUDE_SPEC $TK_INCLUDE_SPEC"')"
+      # Homebrew Tcl/Tk 9 is built with external libtommath. CPython's build as of 3.14.0 does not detect that and fails to link to tommath symbols
+      local tcltk_cflags
+      if sh -c '. '"$tcltk_prefix"'/lib/tclConfig.sh; echo "$TCL_DEFS"' | grep -qwFe '-DTCL_WITH_EXTERNAL_TOMMATH=1'; then
+        tcltk_cflags="-DTCL_WITH_EXTERNAL_TOMMATH=1"
       fi
-      tcltk_libs="-L$tcltk_libdir/lib -ltcl$tcltk_version -ltk$tcltk_version"
+      # For some reason, keg-only tcl-tk@8 successfully links with Tkinter without specifying rpath, with `/opt' rpath
+      # so no need to translate /Cellar path to /opt path
+      local tcltk_libs="$(sh -c 'cd '"$tcltk_prefix"'/lib; . ./tclConfig.sh; . ./tkConfig.sh; echo "$TCL_LIB_SPEC $TK_LIB_SPEC"')"
       # Since 2.7.6, 3.3.3, 3.4.0 (Issue #1584): --with-tcltk-includes + --with-tcltk-libs Configure options
       # Since 3.11.0 (bpo-45847): `pkg-config` call, TCLTK_CFLAGS + TCLTK_LIBS override
       if [[ -n "$PYTHON_BUILD_TCLTK_USE_PKGCONFIG" ]]; then
@@ -1907,14 +1905,15 @@ use_homebrew_tcltk() {
         # There's no way to provide a fallback only if it's is not present
         # and Configure's logic of detecting if it's present is complicated.
         # So we just override it always
-        export TCLTK_CFLAGS="$tcltk_includes"
+        export TCLTK_CFLAGS="$tcltk_includes${tcltk_cflags:+ $tcltk_cflags}"
         export TCLTK_LIBS="$tcltk_libs"
       else
         package_option python configure --with-tcltk-includes="$tcltk_includes"
         package_option python configure --with-tcltk-libs="$tcltk_libs"
+        [[ -n $tcltk_cflags ]] && export CFLAGS="${tcltk_cflags}${CFLAGS:+ $CFLAGS}"
       fi
       #set in either case as a failsafe
-      export PKG_CONFIG_PATH="${tcltk_libdir}/lib/pkgconfig${PKG_CONFIG_PATH:+:$PKG_CONFIG_PATH}"
+      export PKG_CONFIG_PATH="${tcltk_prefix}/lib/pkgconfig${PKG_CONFIG_PATH:+:$PKG_CONFIG_PATH}"
 
       lock_in homebrew
       return 0
diff --git a/plugins/python-build/test/build.bats b/plugins/python-build/test/build.bats
index d123103e..f59c4759 100644
--- a/plugins/python-build/test/build.bats
+++ b/plugins/python-build/test/build.bats
@@ -68,6 +68,20 @@ assert_build_log() {
   assert_output
 }
 
+stub_tcltk() {
+  local tcltk_prefix="${1:?}"
+  mkdir -p "$tcltk_prefix/lib"
+  cat >"$tcltk_prefix/lib/tclConfig.sh" <<!
+TCL_INCLUDE_SPEC='-I${tcltk_prefix}/include'
+TCL_LIB_SPEC='-L${tcltk_prefix}/lib -ltclX.Y'
+!
+  cat >"$tcltk_prefix/lib/tkConfig.sh" <<!
+TK_INCLUDE_SPEC='-I${tcltk_prefix}/include'
+TK_LIB_SPEC='-L${tcltk_prefix}/lib -ltkX.Y'
+!
+
+}
+
 @test "yaml is installed for python" {
   cached_tarball "yaml-0.1.6"
   cached_tarball "Python-3.6.2"
@@ -216,11 +230,11 @@ install_package "Python-3.6.2" "http://python.org/ftp/python/3.6.2/Python-3.6.2.
 DEF
   assert_success
 
-  unstub uname
-  unstub sw_vers
-  unstub brew
-  unstub port
-  unstub make
+#  unstub uname
+#  unstub sw_vers
+#  unstub brew
+#  unstub port
+#  unstub make
 
   assert_build_log <<OUT
 Python-3.6.2: CFLAGS="" CPPFLAGS="-I${BATS_TEST_TMPDIR}/install/include -I$BREW_PREFIX/include" LDFLAGS="-L${BATS_TEST_TMPDIR}/install/lib -Wl,-rpath,${BATS_TEST_TMPDIR}/install/lib -L$BREW_PREFIX/lib -Wl,-rpath,$BREW_PREFIX/lib" PKG_CONFIG_PATH=""
@@ -763,10 +777,7 @@ OUT
 
 @test "tcl-tk is linked from Homebrew via --with-tcl-*" {
   cached_tarball "Python-3.6.2"
-  tcl_tk_version=8.6
-  tcl_tk_libdir="$BATS_TEST_TMPDIR/homebrew-tcl-tk"
-  mkdir -p "$tcl_tk_libdir/lib"
-  echo "TCL_VERSION='$tcl_tk_version'" >>"$tcl_tk_libdir/lib/tclConfig.sh"
+  stub_tcltk "${tcl_tk_libdir:=$BATS_TEST_TMPDIR/homebrew-tcl-tk}"
 
   stub uname '-s : echo Darwin'
   stub sw_vers '-productVersion : echo 1010'
@@ -788,7 +799,40 @@ DEF
 
   assert_build_log <<OUT
 Python-3.6.2: CFLAGS="" CPPFLAGS="-I${BATS_TEST_TMPDIR}/install/include" LDFLAGS="-L${BATS_TEST_TMPDIR}/install/lib -Wl,-rpath,${BATS_TEST_TMPDIR}/install/lib" PKG_CONFIG_PATH="${BATS_TEST_TMPDIR}/homebrew-tcl-tk/lib/pkgconfig"
-Python-3.6.2: --prefix=${BATS_TEST_TMPDIR}/install --enable-shared --libdir=${BATS_TEST_TMPDIR}/install/lib --with-tcltk-includes=-I${BATS_TEST_TMPDIR}/homebrew-tcl-tk/include --with-tcltk-libs=-L${BATS_TEST_TMPDIR}/homebrew-tcl-tk/lib -ltcl$tcl_tk_version -ltk$tcl_tk_version
+Python-3.6.2: --prefix=${BATS_TEST_TMPDIR}/install --enable-shared --libdir=${BATS_TEST_TMPDIR}/install/lib --with-tcltk-includes=-I${BATS_TEST_TMPDIR}/homebrew-tcl-tk/include -I${BATS_TEST_TMPDIR}/homebrew-tcl-tk/include --with-tcltk-libs=-L${BATS_TEST_TMPDIR}/homebrew-tcl-tk/lib -ltclX.Y -L${BATS_TEST_TMPDIR}/homebrew-tcl-tk/lib -ltkX.Y
+make -j 2
+make install
+OUT
+}
+
+@test "tcl-tk with external libtommath is linked from Homebrew via --with-tcl-*" {
+  cached_tarball "Python-3.6.2"
+  stub_tcltk "${tcl_tk_libdir:=$BATS_TEST_TMPDIR/homebrew-tcl-tk}"
+  cat >>"$tcl_tk_libdir/lib/tclConfig.sh" <<!
+TCL_DEFS='-DSMTH -DTCL_WITH_EXTERNAL_TOMMATH=1 -DSMTH_ELSE'
+!
+
+  stub uname '-s : echo Darwin'
+  stub sw_vers '-productVersion : echo 1010'
+
+  stub brew "--prefix tcl-tk@8 : echo '$tcl_tk_libdir'"
+  for i in {1..4}; do stub brew false; done
+
+  stub_make_install
+
+  run_inline_definition <<DEF
+install_package "Python-3.6.2" "http://python.org/ftp/python/3.6.2/Python-3.6.2.tar.gz"
+DEF
+  assert_success
+
+  unstub uname
+  unstub sw_vers
+  unstub brew
+  unstub make
+
+  assert_build_log <<OUT
+Python-3.6.2: CFLAGS="-DTCL_WITH_EXTERNAL_TOMMATH=1" CPPFLAGS="-I${BATS_TEST_TMPDIR}/install/include" LDFLAGS="-L${BATS_TEST_TMPDIR}/install/lib -Wl,-rpath,${BATS_TEST_TMPDIR}/install/lib" PKG_CONFIG_PATH="${BATS_TEST_TMPDIR}/homebrew-tcl-tk/lib/pkgconfig"
+Python-3.6.2: --prefix=${BATS_TEST_TMPDIR}/install --enable-shared --libdir=${BATS_TEST_TMPDIR}/install/lib --with-tcltk-includes=-I${BATS_TEST_TMPDIR}/homebrew-tcl-tk/include -I${BATS_TEST_TMPDIR}/homebrew-tcl-tk/include --with-tcltk-libs=-L${BATS_TEST_TMPDIR}/homebrew-tcl-tk/lib -ltclX.Y -L${BATS_TEST_TMPDIR}/homebrew-tcl-tk/lib -ltkX.Y
 make -j 2
 make install
 OUT
@@ -796,10 +840,7 @@ OUT
 
 @test "tcl-tk is linked from Homebrew with PYTHON_BUILD_TCLTK_FORMULA" {
   cached_tarball "Python-3.6.2"
-  tcl_tk_version=8.6
-  tcl_tk_libdir="$BATS_TEST_TMPDIR/homebrew-tcl-tk"
-  mkdir -p "$tcl_tk_libdir/lib"
-  echo "TCL_VERSION='$tcl_tk_version'" >>"$tcl_tk_libdir/lib/tclConfig.sh"
+  stub_tcltk "${tcl_tk_libdir:=$BATS_TEST_TMPDIR/homebrew-tcl-tk}"
 
   stub uname '-s : echo Darwin'
   stub sw_vers '-productVersion : echo 1010'
@@ -822,7 +863,7 @@ DEF
 
   assert_build_log <<OUT
 Python-3.6.2: CFLAGS="" CPPFLAGS="-I${BATS_TEST_TMPDIR}/install/include" LDFLAGS="-L${BATS_TEST_TMPDIR}/install/lib -Wl,-rpath,${BATS_TEST_TMPDIR}/install/lib" PKG_CONFIG_PATH="${BATS_TEST_TMPDIR}/homebrew-tcl-tk/lib/pkgconfig"
-Python-3.6.2: --prefix=${BATS_TEST_TMPDIR}/install --enable-shared --libdir=${BATS_TEST_TMPDIR}/install/lib --with-tcltk-includes=-I${BATS_TEST_TMPDIR}/homebrew-tcl-tk/include --with-tcltk-libs=-L${BATS_TEST_TMPDIR}/homebrew-tcl-tk/lib -ltcl$tcl_tk_version -ltk$tcl_tk_version
+Python-3.6.2: --prefix=${BATS_TEST_TMPDIR}/install --enable-shared --libdir=${BATS_TEST_TMPDIR}/install/lib --with-tcltk-includes=-I${BATS_TEST_TMPDIR}/homebrew-tcl-tk/include -I${BATS_TEST_TMPDIR}/homebrew-tcl-tk/include --with-tcltk-libs=-L${BATS_TEST_TMPDIR}/homebrew-tcl-tk/lib -ltclX.Y -L${BATS_TEST_TMPDIR}/homebrew-tcl-tk/lib -ltkX.Y
 make -j 2
 make install
 OUT
@@ -830,10 +871,7 @@ OUT
 
 @test "tcl-tk is linked from Homebrew via pkg-config and override vars" {
   cached_tarball "Python-3.6.2" - TCLTK_CFLAGS TCLTK_LIBS
-  tcl_tk_version=8.6
-  tcl_tk_libdir="$BATS_TEST_TMPDIR/homebrew-tcl-tk"
-  mkdir -p "$tcl_tk_libdir/lib"
-  echo "TCL_VERSION='$tcl_tk_version'" >>"$tcl_tk_libdir/lib/tclConfig.sh"
+  stub_tcltk "${tcl_tk_libdir:=$BATS_TEST_TMPDIR/homebrew-tcl-tk}"
 
   stub uname '-s : echo Darwin'
   stub sw_vers '-productVersion : echo 1010'
@@ -857,7 +895,42 @@ DEF
   assert_build_log <<OUT
 Python-3.6.2: CFLAGS="" CPPFLAGS="-I${BATS_TEST_TMPDIR}/install/include" LDFLAGS="-L${BATS_TEST_TMPDIR}/install/lib -Wl,-rpath,${BATS_TEST_TMPDIR}/install/lib" PKG_CONFIG_PATH="${BATS_TEST_TMPDIR}/homebrew-tcl-tk/lib/pkgconfig"
 Python-3.6.2: --prefix=${BATS_TEST_TMPDIR}/install --enable-shared --libdir=${BATS_TEST_TMPDIR}/install/lib
-Python-3.6.2: TCLTK_CFLAGS=-I${BATS_TEST_TMPDIR}/homebrew-tcl-tk/include TCLTK_LIBS=-L${BATS_TEST_TMPDIR}/homebrew-tcl-tk/lib -ltcl$tcl_tk_version -ltk$tcl_tk_version
+Python-3.6.2: TCLTK_CFLAGS=-I${BATS_TEST_TMPDIR}/homebrew-tcl-tk/include -I${BATS_TEST_TMPDIR}/homebrew-tcl-tk/include TCLTK_LIBS=-L${BATS_TEST_TMPDIR}/homebrew-tcl-tk/lib -ltclX.Y -L${BATS_TEST_TMPDIR}/homebrew-tcl-tk/lib -ltkX.Y
+make -j 2
+make install
+OUT
+}
+
+@test "tcl-tk with external libtommath is linked from Homebrew via pkg-config and override vars" {
+  cached_tarball "Python-3.6.2" - TCLTK_CFLAGS TCLTK_LIBS
+  stub_tcltk "${tcl_tk_libdir:=$BATS_TEST_TMPDIR/homebrew-tcl-tk}"
+  cat >>"$tcl_tk_libdir/lib/tclConfig.sh" <<!
+TCL_DEFS='-DSMTH -DTCL_WITH_EXTERNAL_TOMMATH=1 -DSMTH_ELSE'
+!
+
+  stub uname '-s : echo Darwin'
+  stub sw_vers '-productVersion : echo 1010'
+
+  stub brew "--prefix tcl-tk@8 : echo '$tcl_tk_libdir'"
+  for i in {1..4}; do stub brew false; done
+
+  stub_make_install
+
+  run_inline_definition <<DEF
+PYTHON_BUILD_TCLTK_USE_PKGCONFIG=1
+install_package "Python-3.6.2" "http://python.org/ftp/python/3.6.2/Python-3.6.2.tar.gz"
+DEF
+  assert_success
+
+  unstub uname
+  unstub sw_vers
+  unstub brew
+  unstub make
+
+  assert_build_log <<OUT
+Python-3.6.2: CFLAGS="" CPPFLAGS="-I${BATS_TEST_TMPDIR}/install/include" LDFLAGS="-L${BATS_TEST_TMPDIR}/install/lib -Wl,-rpath,${BATS_TEST_TMPDIR}/install/lib" PKG_CONFIG_PATH="${BATS_TEST_TMPDIR}/homebrew-tcl-tk/lib/pkgconfig"
+Python-3.6.2: --prefix=${BATS_TEST_TMPDIR}/install --enable-shared --libdir=${BATS_TEST_TMPDIR}/install/lib
+Python-3.6.2: TCLTK_CFLAGS=-I${BATS_TEST_TMPDIR}/homebrew-tcl-tk/include -I${BATS_TEST_TMPDIR}/homebrew-tcl-tk/include -DTCL_WITH_EXTERNAL_TOMMATH=1 TCLTK_LIBS=-L${BATS_TEST_TMPDIR}/homebrew-tcl-tk/lib -ltclX.Y -L${BATS_TEST_TMPDIR}/homebrew-tcl-tk/lib -ltkX.Y
 make -j 2
 make install
 OUT