diff --git a/scripts/environment/bootstrap-macos-10.sh b/scripts/environment/bootstrap-macos-10.sh
index fb105c2756b81..98fb8910dad12 100755
--- a/scripts/environment/bootstrap-macos-10.sh
+++ b/scripts/environment/bootstrap-macos-10.sh
@@ -6,6 +6,10 @@ unset HOMEBREW_NO_INSTALL_FROM_API
 
 brew update
 
+# `brew install` attempts to upgrade python as a dependency but fails
+# https://github.com/actions/setup-python/issues/577
+brew list -1 | grep python | while read -r formula; do brew unlink "$formula"; brew link --overwrite "$formula"; done
+
 brew install ruby@2.7 coreutils cue-lang/tap/cue protobuf
 
 gem install bundler