diff --git a/lldb/packages/Python/lldbsuite/test/tools/lldb-vscode/lldbvscode_testcase.py b/lldb/packages/Python/lldbsuite/test/tools/lldb-vscode/lldbvscode_testcase.py
--- a/lldb/packages/Python/lldbsuite/test/tools/lldb-vscode/lldbvscode_testcase.py
+++ b/lldb/packages/Python/lldbsuite/test/tools/lldb-vscode/lldbvscode_testcase.py
@@ -239,14 +239,15 @@
 
     def attach(self, program=None, pid=None, waitFor=None, trace=None,
                initCommands=None, preRunCommands=None, stopCommands=None,
-               exitCommands=None, attachCommands=None, coreFile=None):
+               exitCommands=None, attachCommands=None, coreFile=None, disconnectAutomatically=True):
         '''Build the default Makefile target, create the VSCode debug adaptor,
            and attach to the process.
         '''
         # Make sure we disconnect and terminate the VSCode debug adaptor even
         # if we throw an exception during the test case.
         def cleanup():
-            self.vscode.request_disconnect(terminateDebuggee=True)
+            if disconnectAutomatically:
+                self.vscode.request_disconnect(terminateDebuggee=True)
             self.vscode.terminate()
 
         # Execute the cleanup function during test case tear down.
diff --git a/lldb/packages/Python/lldbsuite/test/tools/lldb-vscode/vscode.py b/lldb/packages/Python/lldbsuite/test/tools/lldb-vscode/vscode.py
--- a/lldb/packages/Python/lldbsuite/test/tools/lldb-vscode/vscode.py
+++ b/lldb/packages/Python/lldbsuite/test/tools/lldb-vscode/vscode.py
@@ -473,6 +473,7 @@
             args_dict['attachCommands'] = attachCommands
         if coreFile:
             args_dict['coreFile'] = coreFile
+        args_dict['stopOnEntry'] = True
         command_dict = {
             'command': 'attach',
             'type': 'request',
diff --git a/lldb/test/API/tools/lldb-vscode/disconnect/Makefile b/lldb/test/API/tools/lldb-vscode/disconnect/Makefile
new file mode 100644
--- /dev/null
+++ b/lldb/test/API/tools/lldb-vscode/disconnect/Makefile
@@ -0,0 +1,3 @@
+CXX_SOURCES := main.cpp
+
+include Makefile.rules
diff --git a/lldb/test/API/tools/lldb-vscode/disconnect/TestVSCode_disconnect.py b/lldb/test/API/tools/lldb-vscode/disconnect/TestVSCode_disconnect.py
new file mode 100644
--- /dev/null
+++ b/lldb/test/API/tools/lldb-vscode/disconnect/TestVSCode_disconnect.py
@@ -0,0 +1,82 @@
+"""
+Test lldb-vscode disconnect request
+"""
+
+
+import unittest2
+import vscode
+from lldbsuite.test.decorators import *
+from lldbsuite.test.lldbtest import *
+from lldbsuite.test import lldbutil
+import lldbvscode_testcase
+import subprocess
+import time
+import os
+
+
+class TestVSCode_launch(lldbvscode_testcase.VSCodeTestCaseBase):
+
+    mydir = TestBase.compute_mydir(__file__)
+    source = 'main.cpp'
+
+    def disconnect_and_assert_no_output_printed(self):
+        self.vscode.request_disconnect()
+        # verify we didn't get any input after disconnect
+        time.sleep(2)
+        output = self.get_stdout()
+        self.assertTrue(output is None or len(output) == 0)
+
+    @skipIfWindows
+    @skipIfRemote
+    def test_launch(self):
+        """
+            This test launches a process that would creates a file, but we disconnect
+            before the file is created, which terminates the process and thus the file is not
+            created.
+        """
+        program = self.getBuildArtifact("a.out")
+        self.build_and_launch(program)
+
+        # We set a breakpoint right before the side effect file is created
+        self.set_source_breakpoints(self.source, [line_number(self.source, '// breakpoint')])
+        self.continue_to_next_stop()
+
+        self.vscode.request_disconnect()
+        # verify we didn't produce the side effect file
+        time.sleep(1)
+        self.assertFalse(os.path.exists(program + ".side_effect"))
+
+
+    @skipIfWindows
+    @skipIfRemote
+    def test_attach(self):
+        """
+            This test attaches to a process that creates a file. We attach and disconnect
+            before the file is created, and as the process is not terminated upon disconnection,
+            the file is created anyway.
+        """
+        self.build_and_create_debug_adaptor()
+        program = self.getBuildArtifact("a.out")
+
+        # Use a file as a synchronization point between test and inferior.
+        sync_file_path = lldbutil.append_to_process_working_directory(self,
+            "sync_file_%d" % (int(time.time())))
+        self.addTearDownHook(
+            lambda: self.run_platform_command(
+                "rm %s" %
+                (sync_file_path)))
+
+        self.process = subprocess.Popen([program, sync_file_path])
+        lldbutil.wait_for_file_on_target(self, sync_file_path)
+
+        self.attach(pid=self.process.pid, disconnectAutomatically=False)
+        response = self.vscode.request_evaluate("wait_for_attach = false;")
+        self.assertTrue(response['success'])
+
+        # verify we haven't produced the side effect file yet
+        self.assertFalse(os.path.exists(program + ".side_effect"))
+
+        self.vscode.request_disconnect()
+        time.sleep(2)
+        # verify we produced the side effect file, as the program continued after disconnecting
+        self.assertTrue(os.path.exists(program + ".side_effect"))
diff --git a/lldb/test/API/tools/lldb-vscode/disconnect/main.cpp b/lldb/test/API/tools/lldb-vscode/disconnect/main.cpp
new file mode 100644
--- /dev/null
+++ b/lldb/test/API/tools/lldb-vscode/disconnect/main.cpp
@@ -0,0 +1,33 @@
+#include <chrono>
+#include <cstdio>
+#include <fstream>
+#include <string>
+#include <thread>
+
+volatile bool wait_for_attach = true;
+
+void handle_attach(char *sync_file_path) {
+  lldb_enable_attach();
+
+  {
+    // Create a file to signal that this process has started up.
+    std::ofstream sync_file;
+    sync_file.open(sync_file_path);
+  }
+
+  while (wait_for_attach)
+    std::this_thread::sleep_for(std::chrono::milliseconds(10));
+}
+
+int main(int argc, char **args) {
+  if (argc == 2)
+    handle_attach(args[1]);
+
+  // We let the binary live a little bit to see if it executed after detaching
+  // from // breakpoint
+
+  // Create a file to signal that this process has started up.
+  std::ofstream out_file; // breakpoint
+  out_file.open(std::string(args[0]) + ".side_effect");
+  return 0;
+}
diff --git a/lldb/tools/lldb-vscode/VSCode.h b/lldb/tools/lldb-vscode/VSCode.h
--- a/lldb/tools/lldb-vscode/VSCode.h
+++ b/lldb/tools/lldb-vscode/VSCode.h
@@ -89,6 +89,7 @@
   lldb::tid_t focus_tid;
   bool sent_terminated_event;
   bool stop_at_entry;
+  bool is_attach;
   // Keep track of the last stop thread index IDs as threads won't go away
   // unless we send a "thread" event to indicate the thread exited.
   llvm::DenseSet<lldb::tid_t> thread_ids;
diff --git a/lldb/tools/lldb-vscode/VSCode.cpp b/lldb/tools/lldb-vscode/VSCode.cpp
--- a/lldb/tools/lldb-vscode/VSCode.cpp
+++ b/lldb/tools/lldb-vscode/VSCode.cpp
@@ -38,7 +38,7 @@
            {"swift_catch", "Swift Catch", lldb::eLanguageTypeSwift},
            {"swift_throw", "Swift Throw", lldb::eLanguageTypeSwift}}),
       focus_tid(LLDB_INVALID_THREAD_ID), sent_terminated_event(false),
-      stop_at_entry(false) {
+      stop_at_entry(false), is_attach(false) {
   const char *log_file_path = getenv("LLDBVSCODE_LOG");
 #if defined(_WIN32)
 // Windows opens stdout and stdin in text mode which converts \n to 13,10
diff --git a/lldb/tools/lldb-vscode/lldb-vscode.cpp b/lldb/tools/lldb-vscode/lldb-vscode.cpp
--- a/lldb/tools/lldb-vscode/lldb-vscode.cpp
+++ b/lldb/tools/lldb-vscode/lldb-vscode.cpp
@@ -514,6 +514,7 @@
 //   }]
 // }
 void request_attach(const llvm::json::Object &request) {
+  g_vsc.is_attach = true;
   llvm::json::Object response;
   lldb::SBError error;
   FillResponse(request, response);
@@ -769,7 +770,9 @@
   FillResponse(request, response);
   auto arguments = request.getObject("arguments");
 
-  bool terminateDebuggee = GetBoolean(arguments, "terminateDebuggee", false);
+  bool defaultTerminateDebuggee = g_vsc.is_attach ? false : true;
+  bool terminateDebuggee =
+      GetBoolean(arguments, "terminateDebuggee", defaultTerminateDebuggee);
   lldb::SBProcess process = g_vsc.target.GetProcess();
   auto state = process.GetState();
 
@@ -788,10 +791,9 @@
   case lldb::eStateStopped:
   case lldb::eStateRunning:
     g_vsc.debugger.SetAsync(false);
-    if (terminateDebuggee)
-      process.Kill();
-    else
-      process.Detach();
+    lldb::SBError error = terminateDebuggee ? process.Kill() : process.Detach();
+    if (!error.Success())
+      response.try_emplace("error", error.GetCString());
     g_vsc.debugger.SetAsync(true);
     break;
   }
@@ -1357,6 +1359,7 @@
 //   }]
 // }
 void request_launch(const llvm::json::Object &request) {
+  g_vsc.is_attach = false;
   llvm::json::Object response;
   lldb::SBError error;
   FillResponse(request, response);
diff --git a/lldb/tools/lldb-vscode/package.json b/lldb/tools/lldb-vscode/package.json
--- a/lldb/tools/lldb-vscode/package.json
+++ b/lldb/tools/lldb-vscode/package.json
@@ -162,6 +162,11 @@
 					},
 					"attach": {
 						"properties": {
+							"stopOnEntry": {
+								"type": "boolean",
+								"description": "Automatically stop upon attach.",
+								"default": true
+							},
 							"program": {
 								"type": "string",
 								"description": "Path to the program to attach to."