diff --git a/lldb/test/API/commands/process/attach/TestProcessAttach.py b/lldb/test/API/commands/process/attach/TestProcessAttach.py
--- a/lldb/test/API/commands/process/attach/TestProcessAttach.py
+++ b/lldb/test/API/commands/process/attach/TestProcessAttach.py
@@ -101,6 +101,7 @@
         process = target.GetProcess()
         self.assertTrue(process, PROCESS_IS_VALID)
 
+    @skipIfWindows # This test is flaky on Windows
     @expectedFailureNetBSD
     def test_attach_to_process_by_id_correct_executable_offset(self):
         """
diff --git a/lldb/test/API/commands/target/auto-install-main-executable/TestAutoInstallMainExecutable.py b/lldb/test/API/commands/target/auto-install-main-executable/TestAutoInstallMainExecutable.py
--- a/lldb/test/API/commands/target/auto-install-main-executable/TestAutoInstallMainExecutable.py
+++ b/lldb/test/API/commands/target/auto-install-main-executable/TestAutoInstallMainExecutable.py
@@ -16,6 +16,7 @@
     NO_DEBUG_INFO_TESTCASE = True
 
     @skipIfRemote
+    @skipIfWindows # This test is flaky on Windows
     def test_target_auto_install_main_executable(self):
         if lldbgdbserverutils.get_lldb_server_exe() is None:
           self.skipTest("lldb-server not found")
diff --git a/lldb/test/API/tools/lldb-server/TestGdbRemoteAttachOrWait.py b/lldb/test/API/tools/lldb-server/TestGdbRemoteAttachOrWait.py
--- a/lldb/test/API/tools/lldb-server/TestGdbRemoteAttachOrWait.py
+++ b/lldb/test/API/tools/lldb-server/TestGdbRemoteAttachOrWait.py
@@ -13,6 +13,7 @@
 
     mydir = TestBase.compute_mydir(__file__)
 
+    @skipIfWindows # This test is flaky on Windows
     def test_launch_before_attach_with_vAttachOrWait(self):
         exe = '%s_%d' % (self.testMethodName, os.getpid())
         self.build(dictionary={'EXE': exe})
@@ -57,6 +58,7 @@
         reported_pid = int(pid_text, base=16)
         self.assertEqual(reported_pid, inferior.pid)
 
+    @skipIfWindows # This test is flaky on Windows
     def test_launch_after_attach_with_vAttachOrWait(self):
         exe = '%s_%d' % (self.testMethodName, os.getpid())
         self.build(dictionary={'EXE': exe})
diff --git a/lldb/test/API/tools/lldb-server/TestGdbRemoteAttachWait.py b/lldb/test/API/tools/lldb-server/TestGdbRemoteAttachWait.py
--- a/lldb/test/API/tools/lldb-server/TestGdbRemoteAttachWait.py
+++ b/lldb/test/API/tools/lldb-server/TestGdbRemoteAttachWait.py
@@ -13,6 +13,7 @@
 
     mydir = TestBase.compute_mydir(__file__)
 
+    @skipIfWindows # This test is flaky on Windows
     def test_attach_with_vAttachWait(self):
         exe = '%s_%d' % (self.testMethodName, os.getpid())