diff --git a/pythonFiles/tests/pytestadapter/expected_execution_test_output.py b/pythonFiles/tests/pytestadapter/expected_execution_test_output.py
index 44f3d3d0abce..db4e493c3daa 100644
--- a/pythonFiles/tests/pytestadapter/expected_execution_test_output.py
+++ b/pythonFiles/tests/pytestadapter/expected_execution_test_output.py
@@ -684,3 +684,15 @@
         "subtest": None,
     },
 }
+
+# Constant for the symlink execution test where TEST_DATA_PATH / "root" the target and TEST_DATA_PATH / "symlink_folder" the symlink
+test_a_symlink_path = TEST_DATA_PATH / "symlink_folder" / "tests" / "test_a.py"
+symlink_run_expected_execution_output = {
+    get_absolute_test_id("test_a.py::test_a_function", test_a_symlink_path): {
+        "test": get_absolute_test_id("test_a.py::test_a_function", test_a_symlink_path),
+        "outcome": "success",
+        "message": None,
+        "traceback": None,
+        "subtest": None,
+    }
+}
diff --git a/pythonFiles/tests/pytestadapter/test_execution.py b/pythonFiles/tests/pytestadapter/test_execution.py
index dd32b61fa262..1defe2f52b82 100644
--- a/pythonFiles/tests/pytestadapter/test_execution.py
+++ b/pythonFiles/tests/pytestadapter/test_execution.py
@@ -1,5 +1,6 @@
 # Copyright (c) Microsoft Corporation. All rights reserved.
 # Licensed under the MIT License.
+import json
 import os
 import shutil
 from typing import Any, Dict, List
@@ -8,7 +9,13 @@
 
 from tests.pytestadapter import expected_execution_test_output
 
-from .helpers import TEST_DATA_PATH, runner, runner_with_cwd
+from .helpers import (
+    TEST_DATA_PATH,
+    create_symlink,
+    get_absolute_test_id,
+    runner,
+    runner_with_cwd,
+)
 
 
 def test_config_file():
@@ -276,3 +283,50 @@ def test_pytest_execution(test_ids, expected_const):
         if actual_result_dict[key]["traceback"] is not None:
             actual_result_dict[key]["traceback"] = "TRACEBACK"
     assert actual_result_dict == expected_const
+
+
+def test_symlink_run():
+    """
+    Test to test pytest discovery with the command line arg --rootdir specified as a symlink path.
+    Discovery should succeed and testids should be relative to the symlinked root directory.
+    """
+    with create_symlink(TEST_DATA_PATH, "root", "symlink_folder") as (
+        source,
+        destination,
+    ):
+        assert destination.is_symlink()
+        test_a_path = TEST_DATA_PATH / "symlink_folder" / "tests" / "test_a.py"
+        test_a_id = get_absolute_test_id(
+            "tests/test_a.py::test_a_function",
+            test_a_path,
+        )
+
+        # Run pytest with the cwd being the resolved symlink path (as it will be when we run the subprocess from node).
+        actual = runner_with_cwd(
+            [f"--rootdir={os.fspath(destination)}", test_a_id], source
+        )
+
+        expected_const = (
+            expected_execution_test_output.symlink_run_expected_execution_output
+        )
+        assert actual
+        actual_list: List[Dict[str, Any]] = actual
+        if actual_list is not None:
+            assert actual_list.pop(-1).get("eot")
+            actual_item = actual_list.pop(0)
+            try:
+                # Check if all requirements
+                assert all(
+                    item in actual_item.keys() for item in ("status", "cwd", "result")
+                ), "Required keys are missing"
+                assert actual_item.get("status") == "success", "Status is not 'success'"
+                assert actual_item.get("cwd") == os.fspath(
+                    destination
+                ), f"CWD does not match: {os.fspath(destination)}"
+                actual_result_dict = dict()
+                actual_result_dict.update(actual_item["result"])
+                assert actual_result_dict == expected_const
+            except AssertionError as e:
+                # Print the actual_item in JSON format if an assertion fails
+                print(json.dumps(actual_item, indent=4))
+                pytest.fail(str(e))
diff --git a/pythonFiles/vscode_pytest/__init__.py b/pythonFiles/vscode_pytest/__init__.py
index 256f2bfdb099..bdeefde469f4 100644
--- a/pythonFiles/vscode_pytest/__init__.py
+++ b/pythonFiles/vscode_pytest/__init__.py
@@ -225,6 +225,8 @@ def pytest_report_teststatus(report, config):
     config -- configuration object.
     """
     cwd = pathlib.Path.cwd()
+    if SYMLINK_PATH:
+        cwd = SYMLINK_PATH
 
     if report.when == "call":
         traceback = None
@@ -348,10 +350,7 @@ def pytest_sessionfinish(session, exitstatus):
     cwd = pathlib.Path.cwd()
     if SYMLINK_PATH:
         print("Plugin warning[vscode-pytest]: SYMLINK set, adjusting cwd.")
-        # Get relative between the cwd (resolved path) and the node path.
-        rel_path = os.path.relpath(cwd, pathlib.Path.cwd())
-        # Calculate the new node path by making it relative to the symlink path.
-        cwd = pathlib.Path(os.path.join(SYMLINK_PATH, rel_path))
+        cwd = pathlib.Path(SYMLINK_PATH)
 
     if IS_DISCOVERY:
         if not (exitstatus == 0 or exitstatus == 1 or exitstatus == 5):
@@ -681,9 +680,9 @@ def get_node_path(node: Any) -> pathlib.Path:
     A function that returns the path of a node given the switch to pathlib.Path.
     It also evaluates if the node is a symlink and returns the equivalent path.
     """
-    path = getattr(node, "path", None) or pathlib.Path(node.fspath)
+    node_path = getattr(node, "path", None) or pathlib.Path(node.fspath)
 
-    if not path:
+    if not node_path:
         raise VSCodePytestError(
             f"Unable to find path for node: {node}, node.path: {node.path}, node.fspath: {node.fspath}"
         )
@@ -692,17 +691,24 @@ def get_node_path(node: Any) -> pathlib.Path:
     if SYMLINK_PATH and not isinstance(node, pytest.Session):
         # Get relative between the cwd (resolved path) and the node path.
         try:
-            rel_path = path.relative_to(pathlib.Path.cwd())
-
-            # Calculate the new node path by making it relative to the symlink path.
-            sym_path = pathlib.Path(os.path.join(SYMLINK_PATH, rel_path))
-            return sym_path
+            # check to see if the node path contains the symlink root already
+            common_path = os.path.commonpath([SYMLINK_PATH, node_path])
+            if common_path == os.fsdecode(SYMLINK_PATH):
+                # node path is already relative to the SYMLINK_PATH root therefore return
+                return node_path
+            else:
+                # if the node path is not a symlink, then we need to calculate the equivalent symlink path
+                # get the relative path between the cwd and the node path (as the node path is not a symlink)
+                rel_path = node_path.relative_to(pathlib.Path.cwd())
+                # combine the difference between the cwd and the node path with the symlink path
+                sym_path = pathlib.Path(os.path.join(SYMLINK_PATH, rel_path))
+                return sym_path
         except Exception as e:
             raise VSCodePytestError(
                 f"Error occurred while calculating symlink equivalent from node path: {e}"
-                "\n SYMLINK_PATH: {SYMLINK_PATH}, \n node path: {path}, \n cwd: {{pathlib.Path.cwd()}}"
+                f"\n SYMLINK_PATH: {SYMLINK_PATH}, \n node path: {node_path}, \n cwd: {pathlib.Path.cwd()}"
             )
-    return path
+    return node_path
 
 
 __socket = None