diff --git a/home/.chezmoitemplates/homebrew-library b/home/.chezmoitemplates/homebrew-library
index 4638bfd..79821c3 100644
--- a/home/.chezmoitemplates/homebrew-library
+++ b/home/.chezmoitemplates/homebrew-library
@@ -4,3 +4,18 @@ readonly home_homebrew_prefix="${HOME}/.linuxbrew"
 readonly root_homebrew_prefix="/home/linuxbrew/.linuxbrew"
 
 ensure_path_entry "${home_homebrew_prefix}/bin" "${root_homebrew_prefix}/bin"
+
+# https://github.com/Homebrew/brew/issues/17905#issuecomment-3342150232
+function faketty() {
+  local _system
+  _system="$(uname -s)"
+  if [[ ${_system} == Darwin ]]; then
+    script -qF /dev/null "$(printf "%q " "$@")"
+  else
+    script -qefc "$(printf "%q " "$@")" /dev/null
+  fi
+}
+
+function brew() {
+  faketty brew "${@}"
+}
diff --git a/home/dot_local/bin/executable_full-upgrade.tmpl b/home/dot_local/bin/executable_full-upgrade.tmpl
index 95fcaa2..4bf9fb9 100644
--- a/home/dot_local/bin/executable_full-upgrade.tmpl
+++ b/home/dot_local/bin/executable_full-upgrade.tmpl
@@ -12,6 +12,9 @@ true || source ../../.chezmoitemplates/volta-library
 ensure_path_entry "${HOME}/.local/bin"
 
 if [[ "${CONTINUE_FROM_DOTFILES:-false}" == false ]]; then
+  # Request password early if needed
+  sudo true
+
   if brew --version &>/dev/null; then
     (
       export HOMEBREW_NO_AUTO_UPDATE=1