diff --git a/lldb/packages/Python/lldbsuite/test/tools/lldb-dap/lldbdap_testcase.py b/lldb/packages/Python/lldbsuite/test/tools/lldb-dap/lldbdap_testcase.py
index c51b4b1892951..36471501ea666 100644
--- a/lldb/packages/Python/lldbsuite/test/tools/lldb-dap/lldbdap_testcase.py
+++ b/lldb/packages/Python/lldbsuite/test/tools/lldb-dap/lldbdap_testcase.py
@@ -1,15 +1,16 @@
 import os
 import time
-from typing import Optional
 import uuid
+from typing import Optional
 
 import dap_server
 from dap_server import Source
 from lldbsuite.test.lldbtest import *
-from lldbsuite.test import lldbplatformutil
-import lldbgdbserverutils
 import base64
 
+import lldbgdbserverutils
+from lldbsuite.test import lldbplatformutil
+
 
 class DAPTestCaseBase(TestBase):
     # set timeout based on whether ASAN was enabled or not. Increase
@@ -451,8 +452,25 @@ def attach(
         # if we throw an exception during the test case.
         def cleanup():
             if disconnectAutomatically:
-                self.dap_server.request_disconnect(terminateDebuggee=True)
-            self.dap_server.terminate()
+                try:
+                    self.dap_server.request_disconnect(terminateDebuggee=True)
+                except (
+                    ValueError,
+                    TimeoutError,
+                    BrokenPipeError,
+                    ConnectionError,
+                    Exception,
+                ) as e:
+                    # DAP server might not be responsive, skip disconnect and terminate directly
+                    print(
+                        f"Warning: disconnect failed ({e}), skipping and terminating directly"
+                    )
+            try:
+                self.dap_server.terminate()
+            except Exception as e:
+                print(
+                    f"Warning: terminate failed ({e}), DAP server may have already died"
+                )
 
         # Execute the cleanup function during test case tear down.
         self.addTearDownHook(cleanup)
@@ -462,9 +480,20 @@ def cleanup():
         if expectFailure:
             return response
         if not (response and response["success"]):
-            self.assertTrue(
-                response["success"], "attach failed (%s)" % (response["message"])
-            )
+            error_msg = "attach failed"
+            if response:
+                if "message" in response:
+                    error_msg += " (%s)" % response["message"]
+                elif "body" in response and "error" in response["body"]:
+                    if "format" in response["body"]["error"]:
+                        error_msg += " (%s)" % response["body"]["error"]["format"]
+                    else:
+                        error_msg += " (error in body)"
+                else:
+                    error_msg += " (no error details available)"
+            else:
+                error_msg += " (no response)"
+            self.assertTrue(response and response["success"], error_msg)
 
     def launch(
         self,
diff --git a/lldb/test/API/tools/lldb-dap/attach/TestDAP_attach.py b/lldb/test/API/tools/lldb-dap/attach/TestDAP_attach.py
index 55557e6e0030e..67d3ffaf16250 100644
--- a/lldb/test/API/tools/lldb-dap/attach/TestDAP_attach.py
+++ b/lldb/test/API/tools/lldb-dap/attach/TestDAP_attach.py
@@ -4,12 +4,13 @@
 
 from lldbsuite.test.decorators import *
 from lldbsuite.test.lldbtest import *
-from lldbsuite.test import lldbutil
-import lldbdap_testcase
 import subprocess
 import threading
 import time
 
+import lldbdap_testcase
+from lldbsuite.test import lldbutil
+
 
 def spawn_and_wait(program, delay):
     if delay:
@@ -227,3 +228,46 @@ def test_terminate_commands(self):
             pattern=terminateCommands[0],
         )
         self.verify_commands("terminateCommands", output, terminateCommands)
+
+    def test_session_id_update(self):
+        program = self.build_and_create_debug_adapter_for_attach()
+        self.process = subprocess.Popen(
+            [program],
+            stdin=subprocess.PIPE,
+            stdout=subprocess.PIPE,
+            stderr=subprocess.PIPE,
+        )
+
+        postRunCommands = [
+            "script print('Actual_Session_ID: ' + str(os.getenv('VSCODE_DEBUG_SESSION_ID', 'None')))"
+        ]
+        self.attach(
+            pid=self.process.pid,
+            postRunCommands=postRunCommands,
+        )
+        output = self.get_console()
+        lines = filter(lambda x: "Actual_Session_ID" in x, output.splitlines())
+        self.assertTrue(
+            any("Actual_Session_ID: None" in l for l in lines),
+            "expect session id to be None when not set",
+        )
+
+    def test_session_id_update_empty(self):
+        program = self.build_and_create_debug_adapter_for_attach()
+
+        self.spawn_thread = threading.Thread(
+            target=spawn_and_wait,
+            args=(program, 0.1),
+        )
+        self.spawn_thread.start()
+
+        postRunCommands = [
+            "script print('Actual_Session_ID: ' + str(os.getenv('VSCODE_DEBUG_SESSION_ID', 'None')))"
+        ]
+        self.attach(program=program, postRunCommands=postRunCommands)
+        output = self.get_console()
+        lines = filter(lambda x: "Actual_Session_ID" in x, output.splitlines())
+        self.assertTrue(
+            any("Actual_Session_ID: None" in l for l in lines),
+            "expect session id in console output",
+        )