diff --git a/src/run/run.c b/src/run/run.c
index c0553c7bd9..088c30edcd 100644
--- a/src/run/run.c
+++ b/src/run/run.c
@@ -65,6 +65,7 @@
 #include "unit-def.h"
 #include "unit-name.h"
 #include "user-util.h"
+#include "virt.h"
 
 static bool arg_ask_password = true;
 static bool arg_scope = false;
@@ -3055,6 +3056,12 @@ static bool shall_make_executable_absolute(void) {
                 return false;
         if (arg_transport != BUS_TRANSPORT_LOCAL)
                 return false;
+        if (!empty_or_root(arg_root_directory))
+                return false;
+        /* If we're running in a chroot, our view of the filesystem might be completely different from pid1's
+         * view of the filesystem, hence don't try to resolve the executable in that case. */
+        if (!arg_root_directory && running_in_chroot() > 0)
+                return false;
 
         FOREACH_STRING(f, "RootDirectory=", "RootImage=", "ExecSearchPath=", "MountImages=", "ExtensionImages=")
                 if (strv_find_startswith(arg_property, f))