diff --git a/cli/medperf/cli.py b/cli/medperf/cli.py
index c6524a21a..078d37841 100644
--- a/cli/medperf/cli.py
+++ b/cli/medperf/cli.py
@@ -17,6 +17,7 @@
 import medperf.commands.association.association as association
 import medperf.commands.compatibility_test.compatibility_test as compatibility_test
 import medperf.commands.storage as storage
+from medperf.utils import check_for_updates
 
 app = typer.Typer()
 app.add_typer(mlcube.app, name="mlcube", help="Manage mlcubes")
@@ -99,5 +100,6 @@ def main(
 
     logging.info(f"Running MedPerf v{__version__} on {loglevel} logging level")
     logging.info(f"Executed command: {' '.join(sys.argv[1:])}")
+    check_for_updates()
 
     config.ui.print(f"MedPerf {__version__}")
diff --git a/cli/medperf/commands/execution.py b/cli/medperf/commands/execution.py
index f604c74d0..d8afb2244 100644
--- a/cli/medperf/commands/execution.py
+++ b/cli/medperf/commands/execution.py
@@ -90,7 +90,7 @@ def run_inference(self):
         except ExecutionError as e:
             if not self.ignore_model_errors:
                 logging.error(f"Model MLCube Execution failed: {e}")
-                raise ExecutionError("Model MLCube failed")
+                raise ExecutionError(f"Model MLCube failed: {e}")
             else:
                 self.partial = True
                 logging.warning(f"Model MLCube Execution failed: {e}")
diff --git a/cli/medperf/entities/cube.py b/cli/medperf/entities/cube.py
index 915e15039..6e6f65677 100644
--- a/cli/medperf/entities/cube.py
+++ b/cli/medperf/entities/cube.py
@@ -1,6 +1,5 @@
 import os
 import yaml
-import pexpect
 import logging
 from typing import List, Dict, Optional, Union
 from pydantic import Field
@@ -12,6 +11,7 @@
     remove_path,
     verify_hash,
     generate_tmp_path,
+    spawn_and_kill,
 )
 from medperf.entities.interface import Entity, Uploadable
 from medperf.entities.schemas import MedperfSchema, DeployableSchema
@@ -248,7 +248,8 @@ def _set_image_hash_from_registry(self):
         cmd = f"mlcube --log-level {config.loglevel} inspect --mlcube={self.cube_path} --format=yaml"
         cmd += f" --platform={config.platform} --output-file {tmp_out_yaml}"
         logging.info(f"Running MLCube command: {cmd}")
-        with pexpect.spawn(cmd, timeout=config.mlcube_inspect_timeout) as proc:
+        with spawn_and_kill(cmd, timeout=config.mlcube_inspect_timeout) as proc_wrapper:
+            proc = proc_wrapper.proc
             combine_proc_sp_text(proc)
         if proc.exitstatus != 0:
             raise ExecutionError("There was an error while inspecting the image hash")
@@ -266,7 +267,8 @@ def _get_image_from_registry(self):
         if config.platform == "singularity":
             cmd += f" -Psingularity.image={self._converted_singularity_image_name}"
         logging.info(f"Running MLCube command: {cmd}")
-        with pexpect.spawn(cmd, timeout=config.mlcube_configure_timeout) as proc:
+        with spawn_and_kill(cmd, timeout=config.mlcube_configure_timeout) as proc_wrapper:
+            proc = proc_wrapper.proc
             combine_proc_sp_text(proc)
         if proc.exitstatus != 0:
             raise ExecutionError("There was an error while retrieving the MLCube image")
@@ -361,7 +363,8 @@ def run(
         cmd += " -Pplatform.accelerator_count=0"
 
         logging.info(f"Running MLCube command: {cmd}")
-        with pexpect.spawn(cmd, timeout=timeout) as proc:
+        with spawn_and_kill(cmd, timeout=timeout) as proc_wrapper:
+            proc = proc_wrapper.proc
             proc_out = combine_proc_sp_text(proc)
 
         if output_logs is not None:
diff --git a/cli/medperf/tests/entities/test_cube.py b/cli/medperf/tests/entities/test_cube.py
index 758c64097..c7b8998cc 100644
--- a/cli/medperf/tests/entities/test_cube.py
+++ b/cli/medperf/tests/entities/test_cube.py
@@ -39,8 +39,9 @@ def setup(request, mocker, comms, fs):
 
     # Mock additional third party elements
     mpexpect = MockPexpect(0)
-    mocker.patch(PATCH_CUBE.format("pexpect.spawn"), side_effect=mpexpect.spawn)
+    mocker.patch(PATCH_CUBE.format("spawn_and_kill.spawn"), side_effect=mpexpect.spawn)
     mocker.patch(PATCH_CUBE.format("combine_proc_sp_text"), return_value="")
+    mocker.patch(PATCH_CUBE.format("spawn_and_kill.killpg"), return_value="")
 
     return request.param
 
@@ -95,7 +96,7 @@ def test_download_run_files_without_image_configures_mlcube(
         fs.create_file(
             "tmp_path", contents=yaml.dump({"hash": NO_IMG_CUBE["image_hash"]})
         )
-        spy = mocker.spy(medperf.entities.cube.pexpect, "spawn")
+        spy = mocker.spy(medperf.entities.cube.spawn_and_kill, "spawn")
         expected_cmds = [
             f"mlcube --log-level debug configure --mlcube={self.manifest_path} --platform={config.platform}",
             f"mlcube --log-level debug inspect --mlcube={self.manifest_path}"
@@ -122,7 +123,7 @@ def test_download_run_files_stops_execution_if_configure_fails(
             "tmp_path", contents=yaml.dump({"hash": NO_IMG_CUBE["image_hash"]})
         )
         mpexpect = MockPexpect(1, "expected_hash")
-        mocker.patch("pexpect.spawn", side_effect=mpexpect.spawn)
+        mocker.patch(PATCH_CUBE.format("spawn_and_kill.spawn"), side_effect=mpexpect.spawn)
 
         # Act & Assert
         cube = Cube.get(self.id)
@@ -147,7 +148,7 @@ def test_download_run_files_without_image_fails_with_wrong_hash(
     @pytest.mark.parametrize("setup", [{"remote": [DEFAULT_CUBE]}], indirect=True)
     def test_download_run_files_with_image_isnt_configured(self, mocker, setup):
         # Arrange
-        spy = mocker.spy(medperf.entities.cube.pexpect, "spawn")
+        spy = mocker.spy(medperf.entities.cube.spawn_and_kill, "spawn")
 
         # Act
         cube = Cube.get(self.id)
@@ -175,7 +176,7 @@ def test_cube_runs_command(self, mocker, timeout, setup, task):
         # Arrange
         mpexpect = MockPexpect(0, "expected_hash")
         spy = mocker.patch(
-            PATCH_CUBE.format("pexpect.spawn"), side_effect=mpexpect.spawn
+            PATCH_CUBE.format("spawn_and_kill.spawn"), side_effect=mpexpect.spawn
         )
         mocker.patch(PATCH_CUBE.format("Cube.get_config"), side_effect=["", ""])
         expected_cmd = (
@@ -196,7 +197,7 @@ def test_cube_runs_command(self, mocker, timeout, setup, task):
     def test_cube_runs_command_with_rw_access(self, mocker, setup, task):
         # Arrange
         mpexpect = MockPexpect(0, "expected_hash")
-        spy = mocker.patch("pexpect.spawn", side_effect=mpexpect.spawn)
+        spy = mocker.patch(PATCH_CUBE.format("spawn_and_kill.spawn"), side_effect=mpexpect.spawn)
         mocker.patch(
             PATCH_CUBE.format("Cube.get_config"),
             side_effect=["", ""],
@@ -219,7 +220,7 @@ def test_cube_runs_command_with_rw_access(self, mocker, setup, task):
     def test_cube_runs_command_with_extra_args(self, mocker, setup, task):
         # Arrange
         mpexpect = MockPexpect(0, "expected_hash")
-        spy = mocker.patch("pexpect.spawn", side_effect=mpexpect.spawn)
+        spy = mocker.patch(PATCH_CUBE.format("spawn_and_kill.spawn"), side_effect=mpexpect.spawn)
         mocker.patch(PATCH_CUBE.format("Cube.get_config"), side_effect=["", ""])
         expected_cmd = (
             f"mlcube --log-level debug run --mlcube={self.manifest_path} --task={task} "
@@ -239,7 +240,7 @@ def test_cube_runs_command_with_extra_args(self, mocker, setup, task):
     def test_cube_runs_command_and_preserves_runtime_args(self, mocker, setup, task):
         # Arrange
         mpexpect = MockPexpect(0, "expected_hash")
-        spy = mocker.patch("pexpect.spawn", side_effect=mpexpect.spawn)
+        spy = mocker.patch(PATCH_CUBE.format("spawn_and_kill.spawn"), side_effect=mpexpect.spawn)
         mocker.patch(
             PATCH_CUBE.format("Cube.get_config"),
             side_effect=["cpuarg cpuval", "gpuarg gpuval"],
@@ -262,7 +263,7 @@ def test_cube_runs_command_and_preserves_runtime_args(self, mocker, setup, task)
     def test_run_stops_execution_if_child_fails(self, mocker, setup, task):
         # Arrange
         mpexpect = MockPexpect(1, "expected_hash")
-        mocker.patch("pexpect.spawn", side_effect=mpexpect.spawn)
+        mocker.patch(PATCH_CUBE.format("spawn_and_kill.spawn"), side_effect=mpexpect.spawn)
         mocker.patch(PATCH_CUBE.format("Cube.get_config"), side_effect=["", ""])
 
         # Act & Assert
diff --git a/cli/medperf/tests/mocks/pexpect.py b/cli/medperf/tests/mocks/pexpect.py
index 54dea77b0..83f6811c9 100644
--- a/cli/medperf/tests/mocks/pexpect.py
+++ b/cli/medperf/tests/mocks/pexpect.py
@@ -1,7 +1,8 @@
 class MockChild:
-    def __init__(self, exitstatus, stdout):
+    def __init__(self, exitstatus, stdout, pid):
         self.exitstatus = exitstatus
         self.stdout = stdout
+        self.pid = pid
 
     def __enter__(self, *args, **kwargs):
         return self
@@ -18,11 +19,15 @@ def isalive(self):
     def close(self):
         pass
 
+    def wait(self):
+        pass
+
 
 class MockPexpect:
-    def __init__(self, exitstatus, stdout=""):
+    def __init__(self, exitstatus, stdout="", pid=123456):
         self.exitstatus = exitstatus
         self.stdout = stdout
+        self.pid = pid
 
     def spawn(self, command: str, timeout: int = 30) -> MockChild:
-        return MockChild(self.exitstatus, self.stdout)
+        return MockChild(self.exitstatus, self.stdout, self.pid)
diff --git a/cli/medperf/utils.py b/cli/medperf/utils.py
index 2714f97f0..c054d64c1 100644
--- a/cli/medperf/utils.py
+++ b/cli/medperf/utils.py
@@ -2,6 +2,7 @@
 
 import re
 import os
+import signal
 import yaml
 import random
 import hashlib
@@ -18,6 +19,7 @@
 from typing import List
 from colorama import Fore, Style
 from pexpect.exceptions import TIMEOUT
+from git import Repo, GitCommandError
 import medperf.config as config
 from medperf.exceptions import ExecutionError, MedperfException, InvalidEntityError
 
@@ -438,3 +440,75 @@ def filter_latest_associations(associations, entity_key):
 
     latest_associations = list(latest_associations.values())
     return latest_associations
+
+
+def check_for_updates() -> None:
+    """Check if the current branch is up-to-date with its remote counterpart using GitPython."""
+    repo = Repo(config.BASE_DIR)
+    if repo.bare:
+        logging.debug('Repo is bare')
+        return
+
+    logging.debug(f'Current git commit: {repo.head.commit.hexsha}')
+
+    try:
+        for remote in repo.remotes:
+            remote.fetch()
+
+        if repo.head.is_detached:
+            logging.debug('Repo is in detached state')
+            return
+
+        current_branch = repo.active_branch
+        tracking_branch = current_branch.tracking_branch()
+
+        if tracking_branch is None:
+            logging.debug("Current branch does not track a remote branch.")
+            return
+        if current_branch.commit.hexsha == tracking_branch.commit.hexsha:
+            logging.debug('No git branch updates.')
+            return
+
+        logging.debug(f'Git branch updates found: {current_branch.commit.hexsha} -> {tracking_branch.commit.hexsha}')
+        config.ui.print_warning('MedPerf client updates found. Please, update your MedPerf installation.')
+    except GitCommandError as e:
+        logging.debug('Exception raised during updates check. Maybe user checked out repo with git@ and private key'
+                      'or repo is in detached / non-tracked state?')
+        logging.debug(e)
+
+
+class spawn_and_kill:
+    def __init__(self, cmd, timeout=None, *args, **kwargs):
+        self.cmd = cmd
+        self.timeout = timeout
+        self._args = args
+        self._kwargs = kwargs
+        self.proc: spawn
+        self.exception_occurred = False
+
+    @staticmethod
+    def spawn(*args, **kwargs):
+        return spawn(*args, **kwargs)
+
+    def killpg(self):
+        os.killpg(self.pid, signal.SIGINT)
+
+    def __enter__(self):
+        self.proc = self.spawn(self.cmd, timeout=self.timeout, *self._args, **self._kwargs)
+        self.pid = self.proc.pid
+        return self
+
+    def __exit__(self, exc_type, exc_val, exc_tb):
+        if exc_type:
+            self.exception_occurred = True
+            # Forcefully kill the process group if any exception occurred, in particular,
+            # - KeyboardInterrupt (user pressed Ctrl+C in terminal)
+            # - any other medperf exception like OOM or bug
+            # - pexpect.TIMEOUT
+            logging.info(f'Killing ancestor processes because of exception: {exc_val=}')
+            self.killpg()
+
+        self.proc.close()
+        self.proc.wait()
+        # Return False to propagate exceptions, if any
+        return False
diff --git a/cli/requirements.txt b/cli/requirements.txt
index 4ddb37547..5a5240ba6 100644
--- a/cli/requirements.txt
+++ b/cli/requirements.txt
@@ -21,3 +21,4 @@ schema==0.7.5
 setuptools<=66.1.1
 email-validator==2.0.0
 auth0-python==4.3.0
+GitPython==3.1.41