diff --git a/lldb/packages/Python/lldbsuite/test/lldbplatformutil.py b/lldb/packages/Python/lldbsuite/test/lldbplatformutil.py
index e14c4f8c0d383..719131c9248e8 100644
--- a/lldb/packages/Python/lldbsuite/test/lldbplatformutil.py
+++ b/lldb/packages/Python/lldbsuite/test/lldbplatformutil.py
@@ -4,12 +4,11 @@
 from __future__ import absolute_import
 
 # System modules
-import ctypes
 import itertools
-import os
 import re
 import subprocess
 import sys
+import os
 
 # Third-party modules
 import six
@@ -192,14 +191,3 @@ def hasChattyStderr(test_case):
     if match_android_device(test_case.getArchitecture(), ['aarch64'], range(22, 25+1)):
         return True  # The dynamic linker on the device will complain about unknown DT entries
     return False
-
-if getHostPlatform() == "linux":
-    def enable_attach():
-        """Enable attaching to _this_ process, if host requires such an action.
-        Suitable for use as a preexec_fn in subprocess.Popen and similar."""
-        c = ctypes.CDLL(None)
-        PR_SET_PTRACER = ctypes.c_int(0x59616d61)
-        PR_SET_PTRACER_ANY = ctypes.c_ulong(-1)
-        c.prctl(PR_SET_PTRACER, PR_SET_PTRACER_ANY)
-else:
-    enable_attach = None
diff --git a/lldb/packages/Python/lldbsuite/test/lldbtest.py b/lldb/packages/Python/lldbsuite/test/lldbtest.py
index 22851730153e0..d46e54f30bd55 100644
--- a/lldb/packages/Python/lldbsuite/test/lldbtest.py
+++ b/lldb/packages/Python/lldbsuite/test/lldbtest.py
@@ -393,7 +393,6 @@ def launch(self, executable, args, extra_env):
             stdout=open(
                 os.devnull) if not self._trace_on else None,
             stdin=PIPE,
-            preexec_fn=lldbplatformutil.enable_attach,
             env=env)
 
     def terminate(self):
diff --git a/lldb/test/API/tools/lldb-server/attach-wait/Makefile b/lldb/test/API/tools/lldb-server/attach-wait/Makefile
new file mode 100644
index 0000000000000..22f1051530f87
--- /dev/null
+++ b/lldb/test/API/tools/lldb-server/attach-wait/Makefile
@@ -0,0 +1 @@
+include Makefile.rules
diff --git a/lldb/test/API/tools/lldb-server/TestGdbRemoteAttachWait.py b/lldb/test/API/tools/lldb-server/attach-wait/TestGdbRemoteAttachWait.py
similarity index 75%
rename from lldb/test/API/tools/lldb-server/TestGdbRemoteAttachWait.py
rename to lldb/test/API/tools/lldb-server/attach-wait/TestGdbRemoteAttachWait.py
index ed31b5645c336..b1ec443788bfc 100644
--- a/lldb/test/API/tools/lldb-server/TestGdbRemoteAttachWait.py
+++ b/lldb/test/API/tools/lldb-server/attach-wait/TestGdbRemoteAttachWait.py
@@ -14,10 +14,13 @@ class TestGdbRemoteAttachWait(gdbremote_testcase.GdbRemoteTestCaseBase):
     @skipIfWindows # This test is flaky on Windows
     def test_attach_with_vAttachWait(self):
         exe = '%s_%d' % (self.testMethodName, os.getpid())
+        exe_to_attach = exe
+        sync_file_path = lldbutil.append_to_process_working_directory(self, "process_ready")
+        args = [sync_file_path]
 
         def launch_inferior():
             inferior = self.launch_process_for_attach(
-                inferior_args=["sleep:60"],
+                inferior_args=args,
                 exe_path=self.getBuildArtifact(exe))
             self.assertIsNotNone(inferior)
             self.assertTrue(inferior.pid > 0)
@@ -26,7 +29,14 @@ def launch_inferior():
                     inferior.pid, True))
             return inferior
 
-        self.build(dictionary={'EXE': exe})
+        self.build(dictionary={'EXE': exe, 'CXX_SOURCES': 'main.cpp'})
+        if self.getPlatform() != "windows":
+            # Use a shim to ensure that the process is ready to be attached from
+            # the get-go.
+            args = [self.getBuildArtifact(exe)] + args
+            exe = "shim"
+            self.build(dictionary={'EXE': exe, 'CXX_SOURCES': 'shim.cpp'})
+
         self.set_inferior_startup_attach_manually()
 
         server = self.connect_to_debug_monitor()
@@ -34,11 +44,14 @@ def launch_inferior():
 
         # Launch the first inferior (we shouldn't attach to this one).
         launch_inferior()
-        
+
+        lldbutil.wait_for_file_on_target(self, sync_file_path)
+
         self.do_handshake()
         self.test_sequence.add_log_lines([
             # Do the attach.
-            "read packet: $vAttachWait;{}#00".format(lldbgdbserverutils.gdbremote_hex_encode_string(exe)),
+            "read packet: $vAttachWait;{}#00".format(
+                lldbgdbserverutils.gdbremote_hex_encode_string(exe_to_attach)),
         ], True)
         # Run the stream until attachWait.
         context = self.expect_gdbremote_sequence()
diff --git a/lldb/test/API/tools/lldb-server/attach-wait/main.cpp b/lldb/test/API/tools/lldb-server/attach-wait/main.cpp
new file mode 100644
index 0000000000000..a64622a6c3b95
--- /dev/null
+++ b/lldb/test/API/tools/lldb-server/attach-wait/main.cpp
@@ -0,0 +1,12 @@
+#include <thread>
+#include <fstream>
+
+int main(int argc, char *argv[])
+{
+  if (argc >= 2) {
+    std::ofstream(argv[1]).close();
+  }
+  // Wait to be attached.
+  std::this_thread::sleep_for(std::chrono::minutes(1));
+  return 0;
+}
diff --git a/lldb/test/API/tools/lldb-server/attach-wait/shim.cpp b/lldb/test/API/tools/lldb-server/attach-wait/shim.cpp
new file mode 100644
index 0000000000000..60d0ba3753026
--- /dev/null
+++ b/lldb/test/API/tools/lldb-server/attach-wait/shim.cpp
@@ -0,0 +1,9 @@
+#include <unistd.h>
+#include <cstdio>
+
+int main(int argc, char *argv[]) {
+  lldb_enable_attach();
+  execvp(argv[1], argv+1);
+  perror("execlp");
+  return 1;
+}