diff --git a/cli/medperf/__main__.py b/cli/medperf/__main__.py
index db7c3dbfa..5a7955622 100644
--- a/cli/medperf/__main__.py
+++ b/cli/medperf/__main__.py
@@ -19,6 +19,7 @@
 import medperf.commands.profile as profile
 from medperf.utils import (
     set_custom_config,
+    validate_config,
     set_unique_tmp_config,
     init_storage,
     setup_logging,
@@ -100,6 +101,8 @@ def main(
     # Set inline parameters
     inline_args = ctx.params
     set_custom_config(inline_args)
+    validate_config()
+
     set_unique_tmp_config()
 
     init_storage()
diff --git a/cli/medperf/entities/cube.py b/cli/medperf/entities/cube.py
index 13da6d20f..e5d71d47e 100644
--- a/cli/medperf/entities/cube.py
+++ b/cli/medperf/entities/cube.py
@@ -1,11 +1,16 @@
 import os
+import sys
 import yaml
-import pexpect
 import logging
 from typing import List, Dict, Optional, Union
 from pydantic import Field
 from pathlib import Path
 
+if sys.platform == "win32":
+    import wexpect as pexpect
+else:
+    import pexpect
+
 from medperf.utils import combine_proc_sp_text, list_files, storage_path, verify_hash
 from medperf.entities.interface import Entity, Uploadable
 from medperf.entities.schemas import MedperfSchema, DeployableSchema
@@ -283,7 +288,7 @@ def run(
         proc_out = combine_proc_sp_text(proc)
         proc.close()
         logging.debug(proc_out)
-        if proc.exitstatus != 0:
+        if proc.exitstatus:
             raise ExecutionError("There was an error while executing the cube")
 
         logging.debug(list_files(config.storage))
diff --git a/cli/medperf/utils.py b/cli/medperf/utils.py
index ffe246f00..7b05f0b77 100644
--- a/cli/medperf/utils.py
+++ b/cli/medperf/utils.py
@@ -1,5 +1,6 @@
 from __future__ import annotations
 
+import sys
 import re
 import os
 import yaml
@@ -14,12 +15,16 @@
 import json
 from pathlib import Path
 import shutil
-from pexpect import spawn
 from datetime import datetime
 from typing import List
 from colorama import Fore, Style
 from pexpect.exceptions import TIMEOUT
 
+if sys.platform == "win32":
+    from wexpect import spawn
+else:
+    from pexpect import spawn
+
 import medperf.config as config
 from medperf.logging.filters.redacting_filter import RedactingFilter
 from medperf.exceptions import ExecutionError, MedperfException, InvalidEntityError
@@ -28,7 +33,7 @@
 def setup_logging(log_lvl):
     log_fmt = "%(asctime)s | %(levelname)s: %(message)s"
     log_file = storage_path(config.log_file)
-    handler = handlers.RotatingFileHandler(log_file, backupCount=20)
+    handler = handlers.RotatingFileHandler(log_file, backupCount=20, encoding="utf-8")
     handler.setFormatter(logging.Formatter(log_fmt))
     logging.basicConfig(
         level=log_lvl,
@@ -82,6 +87,13 @@ def set_custom_config(args: dict):
         setattr(config, param, val)
 
 
+def validate_config():
+    """Validates the configuration is valid for the current machine"""
+    if config.platform == "singularity" and sys.platform == "win32":
+        raise MedperfException("Windows doesn't support singularity runner")
+    # Add additional checks here
+
+
 def storage_path(subpath: str):
     """Helper function that converts a path to deployment storage-related path"""
     server_path = config.server.split("//")[1]
@@ -372,7 +384,8 @@ def combine_proc_sp_text(proc: spawn) -> str:
         except TIMEOUT:
             logging.error("Process timed out")
             raise ExecutionError("Process timed out")
-        line = line.decode("utf-8", "ignore")
+        if line is not None and not isinstance(line, str):
+            line = line.decode("utf-8", "ignore")
         if line:
             proc_out += line
             ui.print(f"{Fore.WHITE}{Style.DIM}{line.strip()}{Style.RESET_ALL}")
diff --git a/cli/requirements.txt b/cli/requirements.txt
index e5af407b9..1c2f9c799 100644
--- a/cli/requirements.txt
+++ b/cli/requirements.txt
@@ -1,4 +1,5 @@
-typer~=0.6.0
+typer~=0.6.0; sys_platform != "win32"
+typer<0.5.0; sys_platform == "win32"
 rich~=12.5.0
 PyYAML>=5.4,<6
 requests>=2.26.0
@@ -6,13 +7,14 @@ pydantic==1.10.2
 yaspin==2.1.0
 tabulate==0.8.9
 pexpect==4.8.0
+wexpect==4.0.0; sys_platform == "win32"
 colorama==0.4.4
 time-machine==2.4.0
 pytest-mock==1.13.0
 pyfakefs==5.0.0
 mlcube @ git+https://github.com/mlcommons/mlcube@fb371c960938b495e939bf38b161199d529cf912#subdirectory=mlcube
 mlcube-docker @ git+https://github.com/mlcommons/mlcube@fb371c960938b495e939bf38b161199d529cf912#subdirectory=runners/mlcube_docker
-mlcube-singularity @ git+https://github.com/mlcommons/mlcube@fb371c960938b495e939bf38b161199d529cf912#subdirectory=runners/mlcube_singularity
+mlcube-singularity @ git+https://github.com/mlcommons/mlcube@fb371c960938b495e939bf38b161199d529cf912#subdirectory=runners/mlcube_singularity ; sys_platform != "win32"
 validators==0.18.2
 merge-args==0.1.4
 synapseclient==2.7.0