diff --git a/distrobox b/distrobox
index 73a3a6706a..26ff6d6926 100755
--- a/distrobox
+++ b/distrobox
@@ -62,6 +62,31 @@ distrobox_path="$(dirname "${0}")"
 distrobox_command="${1}"
 shift
 
+# On macOS with Docker Desktop, only paths under $HOME are shared with the
+# Docker Linux VM via VirtioFS.  Scripts installed to /usr/local/bin (e.g.
+# via Homebrew) are not accessible, so Docker creates an empty directory
+# placeholder in the VM, causing "exec: /usr/bin/entrypoint: is a directory".
+#
+# Maintain a managed cache in ~/.local/share/distrobox/ (always under $HOME,
+# always VirtioFS-shared).  Copy each script only when the installed version
+# is newer than the cached copy, so upgrades are picked up automatically.
+if [ "$(uname -s)" = "Darwin" ]; then
+	_dd_data_dir="${XDG_DATA_HOME:-"${HOME}/.local/share"}/distrobox"
+	mkdir -p "${_dd_data_dir}"
+	for _dd_script in distrobox-init distrobox-export distrobox-host-exec; do
+		_dd_src="${distrobox_path}/${_dd_script}"
+		[ ! -f "${_dd_src}" ] && _dd_src="$(command -v "${_dd_script}" 2> /dev/null || true)"
+		if [ -f "${_dd_src}" ]; then
+			_dd_dst="${_dd_data_dir}/${_dd_script}"
+			if [ ! -f "${_dd_dst}" ] || [ "${_dd_src}" -nt "${_dd_dst}" ]; then
+				cp -f "${_dd_src}" "${_dd_dst}"
+				chmod +x "${_dd_dst}"
+			fi
+		fi
+	done
+	unset _dd_script _dd_src _dd_dst _dd_data_dir
+fi
+
 # Simple wrapper to the distrobox utilities.
 # We just detect the 1st argument and launch the matching distrobox utility.
 case "${distrobox_command}" in
diff --git a/distrobox-create b/distrobox-create
index 1731bebcd4..bbd30231cb 100755
--- a/distrobox-create
+++ b/distrobox-create
@@ -102,6 +102,26 @@ distrobox_hostexec_path="$(cd "$(dirname "${0}")" && pwd)/distrobox-host-exec"
 [ ! -e "${distrobox_export_path}" ] && distrobox_export_path="$(command -v distrobox-export)"
 [ ! -e "${distrobox_genentry_path}" ] && distrobox_genentry_path="$(command -v distrobox-generate-entry)"
 [ ! -e "${distrobox_hostexec_path}" ] && distrobox_hostexec_path="$(command -v distrobox-host-exec)"
+# On macOS with Docker Desktop, prefer the managed cache under
+# ~/.local/share/distrobox/ (always VirtioFS-shared) over the installed
+# paths.  The main distrobox entry point keeps the cache up-to-date; when
+# distrobox-create is invoked directly the cache may also exist from a prior
+# run via the main entry point.
+if [ "$(uname -s)" = "Darwin" ]; then
+	_dd_data_dir="${XDG_DATA_HOME:-"${HOME}/.local/share"}/distrobox"
+	for _dd_script in distrobox-init distrobox-export distrobox-host-exec; do
+		_dd_cached="${_dd_data_dir}/${_dd_script}"
+		if [ -f "${_dd_cached}" ]; then
+			case "${_dd_script}" in
+				distrobox-init) distrobox_entrypoint_path="${_dd_cached}" ;;
+				distrobox-export) distrobox_export_path="${_dd_cached}" ;;
+				distrobox-host-exec) distrobox_hostexec_path="${_dd_cached}" ;;
+				*) ;;
+			esac
+		fi
+	done
+	unset _dd_script _dd_cached _dd_data_dir
+fi
 # If the user runs this script as root in a login shell, set rootful=1.
 # There's no need for them to pass the --root flag option in such cases.
 [ "${container_user_uid}" -eq 0 ] && rootful=1 || rootful=0
diff --git a/distrobox-enter b/distrobox-enter
index 93f47761c3..4a59febb56 100755
--- a/distrobox-enter
+++ b/distrobox-enter
@@ -689,6 +689,45 @@ if [ "${container_status}" != "running" ]; then
 	# Here, we save the timestamp before launching the start command, so we can
 	# be sure we're working with this very same session of logs later.
 	log_timestamp="$(date -u +%FT%T).000000000+00:00"
+	# On macOS with Docker Desktop + VirtioFS, only paths under $HOME and a
+	# few system directories (/private, /Volumes) are shared with the Docker
+	# VM.  If distrobox-init lives outside those paths (e.g. /usr/local/bin
+	# from Homebrew), Docker cannot find the bind-mount source in the VM and
+	# creates an empty directory placeholder instead, causing the container
+	# to fail with "exec: /usr/bin/entrypoint: is a directory".
+	#
+	# Detect this by reading the stored bind-mount source from
+	# .HostConfig.Binds (the container config, not .Mounts which is empty
+	# for stopped containers) and checking whether it is accessible as a
+	# file.  If it is not, copy the current distrobox-init to
+	# ~/.local/share/distrobox/ (always under $HOME, always shared) and
+	# write it to the stored source path so the bind-mount resolves to a
+	# file when the container starts.
+	entrypoint_source="$(${container_manager} inspect --type container \
+		--format '{{range .HostConfig.Binds}}{{printf "%s\n" .}}{{end}}' \
+		"${container_name}" 2> /dev/null |
+		grep ':/usr/bin/entrypoint' | cut -d: -f1)"
+	# On macOS with Docker Desktop, .HostConfig.Binds may store paths with a
+	# /host_mnt prefix (Docker Desktop's VirtioFS mount prefix in the Linux VM).
+	# Strip the prefix to get the actual macOS path for the file-existence check.
+	entrypoint_source_check="${entrypoint_source}"
+	if [ "$(uname -s)" = "Darwin" ]; then
+		entrypoint_source_check="${entrypoint_source_check#/host_mnt}"
+	fi
+	if [ -n "${entrypoint_source}" ] && [ ! -f "${entrypoint_source_check}" ]; then
+		distrobox_entrypoint_path="$(cd "$(dirname "${0}")" && pwd)/distrobox-init"
+		[ ! -f "${distrobox_entrypoint_path}" ] &&
+			distrobox_entrypoint_path="$(command -v distrobox-init 2> /dev/null)"
+		if [ -f "${distrobox_entrypoint_path}" ]; then
+			# Remove Docker's empty-directory placeholder (if present) and
+			# replace it with the actual script so the bind-mount works.
+			[ -d "${entrypoint_source}" ] && rmdir "${entrypoint_source}" 2> /dev/null
+			mkdir -p "$(dirname "${entrypoint_source}")"
+			cp "${distrobox_entrypoint_path}" "${entrypoint_source}"
+			chmod +x "${entrypoint_source}"
+		fi
+	fi
+	unset entrypoint_source entrypoint_source_check
 	${container_manager} start "${container_name}" > /dev/null
 	#
 	# Check if the container is going in error status earlier than the