diff --git a/lldb/tools/debugserver/source/DNB.cpp b/lldb/tools/debugserver/source/DNB.cpp
--- a/lldb/tools/debugserver/source/DNB.cpp
+++ b/lldb/tools/debugserver/source/DNB.cpp
@@ -382,11 +382,22 @@
         if (err_str && err_len > 0) {
           if (launch_err.AsString()) {
             ::snprintf(err_str, err_len,
-                       "failed to get the task for process %i (%s)", pid,
+                       "failed to get the task for process %i: %s", pid,
                        launch_err.AsString());
           } else {
+
+            const char *ent_name =
+#if TARGET_OS_OSX
+              "com.apple.security.get-task-allow";
+#else
+              "get-task-allow";
+#endif
             ::snprintf(err_str, err_len,
-                       "failed to get the task for process %i", pid);
+                       "failed to get the task for process %i: this likely "
+                       "means the process cannot be debugged, either because "
+                       "it's a system process or because the process is "
+                       "missing the %s entitlement.",
+                       pid, ent_name);
           }
         }
       } else {