diff --git a/src/core/dbus-execute.c b/src/core/dbus-execute.c
index dfcc2ee6e7..753b91d511 100644
--- a/src/core/dbus-execute.c
+++ b/src/core/dbus-execute.c
@@ -1354,8 +1354,10 @@ int bus_set_transient_exec_command(
                 if (r < 0)
                         return r;
 
-                if (!path_is_absolute(path))
-                        return sd_bus_error_setf(error, SD_BUS_ERROR_INVALID_ARGS, "Path %s is not absolute.", path);
+                if (!path_is_absolute(path) && !filename_is_valid(path))
+                        return sd_bus_error_setf(error, SD_BUS_ERROR_INVALID_ARGS,
+                                                 "\"%s\" is neither a valid executable name nor an absolute path",
+                                                 path);
 
                 r = sd_bus_message_read_strv(message, &argv);
                 if (r < 0)
diff --git a/src/run/run.c b/src/run/run.c
index bdd82c085a..214b269569 100644
--- a/src/run/run.c
+++ b/src/run/run.c
@@ -1720,11 +1720,15 @@ static int run(int argc, char* argv[]) {
         if (r <= 0)
                 return r;
 
-        if (!strv_isempty(arg_cmdline) && arg_transport == BUS_TRANSPORT_LOCAL) {
+        if (!strv_isempty(arg_cmdline) &&
+            arg_transport == BUS_TRANSPORT_LOCAL &&
+            !strv_find_startswith(arg_property, "RootDirectory=") &&
+            !strv_find_startswith(arg_property, "RootImage=")) {
+                /* Patch in an absolute path to fail early for user convenience, but only when we can do it
+                 * (i.e. we will be running from the same file system). This also uses the user's $PATH,
+                 * while we use a fixed search path in the manager. */
+
                 _cleanup_free_ char *command = NULL;
-
-                /* Patch in an absolute path */
-
                 r = find_executable(arg_cmdline[0], &command);
                 if (r < 0)
                         return log_error_errno(r, "Failed to find executable %s: %m", arg_cmdline[0]);