diff --git a/src/azure-cli-core/azure/cli/core/__init__.py b/src/azure-cli-core/azure/cli/core/__init__.py
index c4dfc7f8b22..fb2f2ad3af3 100644
--- a/src/azure-cli-core/azure/cli/core/__init__.py
+++ b/src/azure-cli-core/azure/cli/core/__init__.py
@@ -622,9 +622,9 @@ def __init__(self, mod_name, suppress_extension_name, suppress_up_to_version, re
         self.recommend_update = recommend_update
 
     def handle_suppress(self, ext):
-        from pkg_resources import parse_version
+        from packaging.version import parse
         should_suppress = ext.name == self.suppress_extension_name and ext.version and \
-            parse_version(ext.version) <= parse_version(self.suppress_up_to_version)
+            parse(ext.version) <= parse(self.suppress_up_to_version)
         if should_suppress:
             reason = self.reason or "Use --debug for more information."
             logger.warning("Extension %s (%s) has been suppressed. %s",
diff --git a/src/azure-cli-core/azure/cli/core/extension/__init__.py b/src/azure-cli-core/azure/cli/core/extension/__init__.py
index 89a75d83108..50bdea534f7 100644
--- a/src/azure-cli-core/azure/cli/core/extension/__init__.py
+++ b/src/azure-cli-core/azure/cli/core/extension/__init__.py
@@ -280,20 +280,20 @@ def _collect(path, depth=0, max_depth=3):
 
 def ext_compat_with_cli(azext_metadata):
     from azure.cli.core import __version__ as core_version
-    from pkg_resources import parse_version
+    from packaging.version import parse
     is_compatible, min_required, max_required = (True, None, None)
     if azext_metadata:
         min_required = azext_metadata.get(EXT_METADATA_MINCLICOREVERSION)
         max_required = azext_metadata.get(EXT_METADATA_MAXCLICOREVERSION)
-        parsed_cli_version = parse_version(core_version)
-        if min_required and parsed_cli_version < parse_version(min_required):
+        parsed_cli_version = parse(core_version)
+        if min_required and parsed_cli_version < parse(min_required):
             is_compatible = False
-        elif max_required and parsed_cli_version > parse_version(max_required):
+        elif max_required and parsed_cli_version > parse(max_required):
             is_compatible = False
 
     try:
         min_ext_required = EXTENSION_VERSION_REQUIREMENTS.get(azext_metadata.get('name')).get(MIN_EXT_VERSION)
-        if parse_version(azext_metadata.get('version')) < parse_version(min_ext_required):
+        if parse(azext_metadata.get('version')) < parse(min_ext_required):
             is_compatible = False
     except AttributeError:
         min_ext_required = None
diff --git a/src/azure-cli-core/azure/cli/core/extension/_resolve.py b/src/azure-cli-core/azure/cli/core/extension/_resolve.py
index 40841be48fc..f29d338c967 100644
--- a/src/azure-cli-core/azure/cli/core/extension/_resolve.py
+++ b/src/azure-cli-core/azure/cli/core/extension/_resolve.py
@@ -2,7 +2,7 @@
 # Copyright (c) Microsoft Corporation. All rights reserved.
 # Licensed under the MIT License. See License.txt in the project root for license information.
 # --------------------------------------------------------------------------------------------
-from pkg_resources import parse_version
+from packaging.version import parse
 
 from azure.cli.core.extension import ext_compat_with_cli, WHEEL_INFO_RE
 from azure.cli.core.extension._index import get_index_extensions
@@ -43,10 +43,10 @@ def _is_compatible_with_cli_version(item):
 def _is_greater_than_cur_version(cur_version):
     if not cur_version:
         return None
-    cur_version_parsed = parse_version(cur_version)
+    cur_version_parsed = parse(cur_version)
 
     def filter_func(item):
-        item_version = parse_version(item['metadata']['version'])
+        item_version = parse(item['metadata']['version'])
         if item_version > cur_version_parsed:
             return True
         logger.debug("Skipping '%s' as %s not greater than current version %s", item['filename'],
@@ -76,7 +76,7 @@ def resolve_from_index(extension_name, cur_version=None, index_url=None, target_
     if not candidates:
         raise NoExtensionCandidatesError("No suitable extensions found.")
 
-    candidates_sorted = sorted(candidates, key=lambda c: parse_version(c['metadata']['version']), reverse=True)
+    candidates_sorted = sorted(candidates, key=lambda c: parse(c['metadata']['version']), reverse=True)
     logger.debug("Candidates %s", [c['filename'] for c in candidates_sorted])
 
     if target_version:
diff --git a/src/azure-cli-core/azure/cli/core/extension/operations.py b/src/azure-cli-core/azure/cli/core/extension/operations.py
index fff8b7357d0..b43aabe23d0 100644
--- a/src/azure-cli-core/azure/cli/core/extension/operations.py
+++ b/src/azure-cli-core/azure/cli/core/extension/operations.py
@@ -15,7 +15,7 @@
 from subprocess import check_output, STDOUT, CalledProcessError
 from urllib.parse import urlparse
 
-from pkg_resources import parse_version
+from packaging.version import parse
 
 from azure.cli.core import CommandIndex
 from azure.cli.core.util import CLIError, reload_module
@@ -439,12 +439,12 @@ def list_available_extensions(index_url=None, show_details=False, cli_ctx=None):
         if not items:
             continue
 
-        latest = max(items, key=lambda c: parse_version(c['metadata']['version']))
+        latest = max(items, key=lambda c: parse(c['metadata']['version']))
         installed = False
         if name in installed_extension_names:
             installed = True
             ext_version = get_extension(name).version
-            if ext_version and parse_version(latest['metadata']['version']) > parse_version(ext_version):
+            if ext_version and parse(latest['metadata']['version']) > parse(ext_version):
                 installed = str(True) + ' (upgrade available)'
         results.append({
             'name': name,
@@ -473,13 +473,13 @@ def list_versions(extension_name, index_url=None, cli_ctx=None):
     results = []
     latest_compatible_version = None
 
-    for ext in sorted(exts, key=lambda c: parse_version(c['metadata']['version']), reverse=True):
+    for ext in sorted(exts, key=lambda c: parse(c['metadata']['version']), reverse=True):
         compatible = ext_compat_with_cli(ext['metadata'])[0]
         ext_version = ext['metadata']['version']
         if latest_compatible_version is None and compatible:
             latest_compatible_version = ext_version
         installed = ext_version == installed_ext.version if installed_ext else False
-        if installed and parse_version(latest_compatible_version) > parse_version(installed_ext.version):
+        if installed and parse(latest_compatible_version) > parse(installed_ext.version):
             installed = str(True) + ' (upgrade available)'
         version = ext['metadata']['version']
         if latest_compatible_version == ext_version:
diff --git a/src/azure-cli-core/azure/cli/core/util.py b/src/azure-cli-core/azure/cli/core/util.py
index 424574ee83a..187b3176ab7 100644
--- a/src/azure-cli-core/azure/cli/core/util.py
+++ b/src/azure-cli-core/azure/cli/core/util.py
@@ -352,10 +352,10 @@ def _print(val=''):
         print(val, file=output)
 
     def _get_version_string(name, version_dict):
-        from distutils.version import LooseVersion  # pylint: disable=import-error,no-name-in-module
+        from packaging.version import parse  # pylint: disable=import-error,no-name-in-module
         local = version_dict['local']
         pypi = version_dict.get('pypi', None)
-        if pypi and LooseVersion(pypi) > LooseVersion(local):
+        if pypi and parse(pypi) > parse(local):
             return name.ljust(25) + local.rjust(15) + ' *'
         return name.ljust(25) + local.rjust(15)
 
@@ -1180,11 +1180,11 @@ def handle_version_update():
     """
     try:
         from azure.cli.core._session import VERSIONS
-        from distutils.version import LooseVersion  # pylint: disable=import-error,no-name-in-module
+        from packaging.version import parse  # pylint: disable=import-error,no-name-in-module
         from azure.cli.core import __version__
         if not VERSIONS['versions']:
             get_cached_latest_versions()
-        elif LooseVersion(VERSIONS['versions']['core']['local']) != LooseVersion(__version__):
+        elif parse(VERSIONS['versions']['core']['local']) != parse(__version__):
             logger.debug("Azure CLI has been updated.")
             logger.debug("Clean up versions and refresh cloud endpoints information in local files.")
             VERSIONS['versions'] = {}
diff --git a/src/azure-cli/azure/cli/__main__.py b/src/azure-cli/azure/cli/__main__.py
index 7e315c4456e..ebe4773c1ca 100644
--- a/src/azure-cli/azure/cli/__main__.py
+++ b/src/azure-cli/azure/cli/__main__.py
@@ -81,8 +81,8 @@ def cli_main(cli, args):
                 version_update_time = datetime.datetime.strptime(VERSIONS[_VERSION_UPDATE_TIME], '%Y-%m-%d %H:%M:%S.%f')
                 if datetime.datetime.now() > version_update_time + datetime.timedelta(days=11):
                     get_cached_latest_versions()
-                from distutils.version import LooseVersion
-                if LooseVersion(VERSIONS['versions']['core']['local']) < LooseVersion(VERSIONS['versions']['core']['pypi']):  # pylint: disable=line-too-long
+                from packaging.version import parse
+                if parse(VERSIONS['versions']['core']['local']) < parse(VERSIONS['versions']['core']['pypi']):  # pylint: disable=line-too-long
                     import subprocess
                     import platform
                     from azure.cli.core.azclierror import UnclassifiedUserFault  # pylint: disable=ungrouped-imports
diff --git a/src/azure-cli/azure/cli/command_modules/acr/check_health.py b/src/azure-cli/azure/cli/command_modules/acr/check_health.py
index dea06a33da9..d9737bff87b 100644
--- a/src/azure-cli/azure/cli/command_modules/acr/check_health.py
+++ b/src/azure-cli/azure/cli/command_modules/acr/check_health.py
@@ -138,7 +138,7 @@ def _get_cli_version():
 # Get helm versions
 def _get_helm_version(ignore_errors):
     from ._errors import HELM_VERSION_ERROR
-    from distutils.version import LooseVersion  # pylint: disable=import-error,no-name-in-module
+    from packaging.version import parse  # pylint: disable=import-error,no-name-in-module
 
     # Helm command check
     helm_command, error = get_helm_command(is_diagnostics_context=True)
@@ -165,7 +165,7 @@ def _get_helm_version(ignore_errors):
     logger.warning("Helm version: %s", output)
 
     # Display an error message if the current helm version < min required version
-    if match_obj and LooseVersion(output) < LooseVersion(MIN_HELM_VERSION):
+    if match_obj and parse(output) < parse(MIN_HELM_VERSION):
         obsolete_ver_error = HELM_VERSION_ERROR.set_error_message(
             "Current Helm client version is not recommended. Please upgrade your Helm client to at least version {}."
             .format(MIN_HELM_VERSION))
@@ -175,7 +175,7 @@ def _get_helm_version(ignore_errors):
 def _get_notary_version(ignore_errors):
     from ._errors import NOTARY_VERSION_ERROR
     from .notary import get_notary_command
-    from distutils.version import LooseVersion  # pylint: disable=import-error,no-name-in-module
+    from packaging.version import parse  # pylint: disable=import-error,no-name-in-module
 
     # Notary command check
     notary_command, error = get_notary_command(is_diagnostics_context=True)
@@ -202,9 +202,9 @@ def _get_notary_version(ignore_errors):
     logger.warning("Notary version: %s", output)
 
     # Display error if the current version does not match the recommended version
-    if match_obj and LooseVersion(output) != LooseVersion(RECOMMENDED_NOTARY_VERSION):
+    if match_obj and parse(output) != parse(RECOMMENDED_NOTARY_VERSION):
         version_msg = "upgrade"
-        if LooseVersion(output) > LooseVersion(RECOMMENDED_NOTARY_VERSION):
+        if parse(output) > parse(RECOMMENDED_NOTARY_VERSION):
             version_msg = "downgrade"
         obsolete_ver_error = NOTARY_VERSION_ERROR.set_error_message(
             "Current notary version is not recommended. Please {} your notary client to version {}."
diff --git a/src/azure-cli/azure/cli/command_modules/find/custom.py b/src/azure-cli/azure/cli/command_modules/find/custom.py
index f59a9202ca4..714fc25e7ce 100644
--- a/src/azure-cli/azure/cli/command_modules/find/custom.py
+++ b/src/azure-cli/azure/cli/command_modules/find/custom.py
@@ -16,7 +16,7 @@
 from azure.cli.core import telemetry as telemetry_core
 from azure.cli.core import __version__ as core_version
 from azure.cli.core.commands.constants import SURVEY_PROMPT
-from pkg_resources import parse_version
+from packaging.version import parse
 from knack.log import get_logger
 logger = get_logger(__name__)
 
@@ -94,7 +94,7 @@ def should_enable_styling():
 
 
 def call_aladdin_service(query):
-    version = str(parse_version(core_version))
+    version = str(parse(core_version))
     correlation_id = telemetry_core._session.correlation_id   # pylint: disable=protected-access
     subscription_id = telemetry_core._get_azure_subscription_id()  # pylint: disable=protected-access
 
diff --git a/src/azure-cli/azure/cli/command_modules/util/custom.py b/src/azure-cli/azure/cli/command_modules/util/custom.py
index eb7025a2f6c..8672c7caf57 100644
--- a/src/azure-cli/azure/cli/command_modules/util/custom.py
+++ b/src/azure-cli/azure/cli/command_modules/util/custom.py
@@ -40,14 +40,14 @@ def upgrade_version(cmd, update_all=None, yes=None):  # pylint: disable=too-many
     from azure.cli.core import __version__ as local_version
     from azure.cli.core._environment import _ENV_AZ_INSTALLER
     from azure.cli.core.extension import get_extensions, WheelExtension
-    from distutils.version import LooseVersion
+    from packaging.version import parse
     from knack.util import CLIError
 
     update_cli = True
     from azure.cli.core.util import get_latest_from_github
     try:
         latest_version = get_latest_from_github()
-        if latest_version and LooseVersion(latest_version) <= LooseVersion(local_version):
+        if latest_version and parse(latest_version) <= parse(local_version):
             logger.warning("You already have the latest azure-cli version: %s", local_version)
             update_cli = False
             if not update_all:
diff --git a/src/azure-cli/azure/cli/command_modules/vm/_actions.py b/src/azure-cli/azure/cli/command_modules/vm/_actions.py
index 558e96ca9b3..8eaadadfb2a 100644
--- a/src/azure-cli/azure/cli/command_modules/vm/_actions.py
+++ b/src/azure-cli/azure/cli/command_modules/vm/_actions.py
@@ -147,7 +147,7 @@ def load_images_from_aliases_doc(cli_ctx, publisher=None, offer=None, sku=None):
 def load_extension_images_thru_services(cli_ctx, publisher, name, version, location,
                                         show_latest=False, partial_match=True):
     from concurrent.futures import ThreadPoolExecutor, as_completed
-    from distutils.version import LooseVersion  # pylint: disable=no-name-in-module,import-error
+    from packaging.version import parse  # pylint: disable=no-name-in-module,import-error
     all_images = []
     client = _compute_client_factory(cli_ctx)
     if location is None:
@@ -175,7 +175,7 @@ def _load_extension_images_from_publisher(publisher):
 
             if show_latest:
                 # pylint: disable=no-member
-                versions.sort(key=lambda v: LooseVersion(v.name), reverse=True)
+                versions.sort(key=lambda v: parse(v.name), reverse=True)
                 try:
                     all_images.append({
                         'publisher': publisher,
diff --git a/src/azure-cli/azure/cli/command_modules/vm/custom.py b/src/azure-cli/azure/cli/command_modules/vm/custom.py
index abd2a5ee5e4..cd00f67ad43 100644
--- a/src/azure-cli/azure/cli/command_modules/vm/custom.py
+++ b/src/azure-cli/azure/cli/command_modules/vm/custom.py
@@ -114,10 +114,10 @@ def _get_access_extension_upgrade_info(extensions, name):
 
     if extensions:
         extension = next((e for e in extensions if e.name == name), None)
-        from distutils.version import LooseVersion  # pylint: disable=no-name-in-module,import-error
-        if extension and LooseVersion(extension.type_handler_version) < LooseVersion(version):
+        from packaging.version import parse  # pylint: disable=no-name-in-module,import-error
+        if extension and parse(extension.type_handler_version) < parse(version):
             auto_upgrade = True
-        elif extension and LooseVersion(extension.type_handler_version) > LooseVersion(version):
+        elif extension and parse(extension.type_handler_version) > parse(version):
             version = extension.type_handler_version
 
     return publisher, version, auto_upgrade
diff --git a/src/azure-cli/requirements.py3.Darwin.txt b/src/azure-cli/requirements.py3.Darwin.txt
index 6e2143f1246..1b6b0d9f106 100644
--- a/src/azure-cli/requirements.py3.Darwin.txt
+++ b/src/azure-cli/requirements.py3.Darwin.txt
@@ -112,6 +112,7 @@ msal==1.10.0
 msrest==0.6.21
 msrestazure==0.6.3
 oauthlib==3.0.1
+packaging==20.9
 paramiko==2.6.0
 pbr==5.3.1
 portalocker==1.7.1
diff --git a/src/azure-cli/requirements.py3.Linux.txt b/src/azure-cli/requirements.py3.Linux.txt
index 4d4bfcb83e7..c03134381cf 100644
--- a/src/azure-cli/requirements.py3.Linux.txt
+++ b/src/azure-cli/requirements.py3.Linux.txt
@@ -112,6 +112,7 @@ msal==1.10.0
 msrest==0.6.21
 msrestazure==0.6.3
 oauthlib==3.0.1
+packaging==20.9
 paramiko==2.6.0
 pbr==5.3.1
 portalocker==1.7.1
diff --git a/src/azure-cli/requirements.py3.windows.txt b/src/azure-cli/requirements.py3.windows.txt
index 68d8bd8aceb..ec33d3fb5b3 100644
--- a/src/azure-cli/requirements.py3.windows.txt
+++ b/src/azure-cli/requirements.py3.windows.txt
@@ -111,6 +111,7 @@ msal==1.10.0
 msrest==0.6.21
 msrestazure==0.6.3
 oauthlib==3.0.1
+packaging==20.9
 paramiko==2.6.0
 pbr==5.3.1
 portalocker==1.7.1
diff --git a/src/azure-cli/setup.py b/src/azure-cli/setup.py
index 6e2c466da1e..32c8b7bbb64 100644
--- a/src/azure-cli/setup.py
+++ b/src/azure-cli/setup.py
@@ -136,6 +136,7 @@
     'javaproperties==0.5.1',
     'jsmin~=2.2.2',
     'jsondiff==1.2.0',
+    'packaging~=20.9',
     'pytz==2019.1',
     'scp~=0.13.2',
     'semver==2.13.0',