diff --git a/elementary/clients/slack/client.py b/elementary/clients/slack/client.py
index fb366d60b..10fa141e2 100644
--- a/elementary/clients/slack/client.py
+++ b/elementary/clients/slack/client.py
@@ -1,7 +1,9 @@
 import json
+import ssl
 from abc import ABC, abstractmethod
 from typing import Dict, List, Optional, Tuple
 
+import certifi
 from ratelimit import limits, sleep_and_retry
 from slack_sdk import WebClient, WebhookClient
 from slack_sdk.errors import SlackApiError
@@ -24,8 +26,9 @@ class SlackClient(ABC):
     def __init__(
         self,
         tracking: Optional[Tracking] = None,
+        ssl_context: Optional[ssl.SSLContext] = None,
     ):
-        self.client = self._initial_client()
+        self.client = self._initial_client(ssl_context)
         self.tracking = tracking
         self._initial_retry_handlers()
         self.email_to_user_id_cache: Dict[str, str] = {}
@@ -37,15 +40,35 @@ def create_client(
         if not config.has_slack:
             return None
         if config.slack_token:
-            logger.debug("Creating Slack client with token.")
-            return SlackWebClient(token=config.slack_token, tracking=tracking)
+            logger.debug(
+                "Creating Slack client with token (system CA? = %s).",
+                config.use_system_ca_files,
+            )
+            ssl_context = (
+                None
+                if config.use_system_ca_files
+                else ssl.create_default_context(cafile=certifi.where())
+            )
+            return SlackWebClient(
+                token=config.slack_token, tracking=tracking, ssl_context=ssl_context
+            )
         elif config.slack_webhook:
-            logger.debug("Creating Slack client with webhook.")
-            return SlackWebhookClient(webhook=config.slack_webhook, tracking=tracking)
+            logger.debug(
+                "Creating Slack client with webhook (system CA? = %s).",
+                config.use_system_ca_files,
+            )
+            ssl_context = (
+                ssl.create_default_context(cafile=certifi.where())
+                if not config.use_system_ca_files
+                else None
+            )
+            return SlackWebhookClient(
+                webhook=config.slack_webhook, tracking=tracking, ssl_context=ssl_context
+            )
         return None
 
     @abstractmethod
-    def _initial_client(self):
+    def _initial_client(self, ssl_context: Optional[ssl.SSLContext]):
         raise NotImplementedError
 
     def _initial_retry_handlers(self):
@@ -79,12 +102,13 @@ def __init__(
         self,
         token: str,
         tracking: Optional[Tracking] = None,
+        ssl_context: Optional[ssl.SSLContext] = None,
     ):
         self.token = token
-        super().__init__(tracking)
+        super().__init__(tracking, ssl_context)
 
-    def _initial_client(self):
-        return WebClient(token=self.token)
+    def _initial_client(self, ssl_context: Optional[ssl.SSLContext]):
+        return WebClient(token=self.token, ssl=ssl_context)
 
     @sleep_and_retry
     @limits(calls=1, period=ONE_SECOND)
@@ -224,13 +248,16 @@ def __init__(
         self,
         webhook: str,
         tracking: Optional[Tracking] = None,
+        ssl_context: Optional[ssl.SSLContext] = None,
     ):
         self.webhook = webhook
-        super().__init__(tracking)
+        super().__init__(tracking, ssl_context)
 
-    def _initial_client(self):
+    def _initial_client(self, ssl_context: Optional[ssl.SSLContext]):
         return WebhookClient(
-            url=self.webhook, default_headers={"Content-type": "application/json"}
+            url=self.webhook,
+            default_headers={"Content-type": "application/json"},
+            ssl=ssl_context,
         )
 
     @sleep_and_retry
diff --git a/elementary/config/config.py b/elementary/config/config.py
index 3eaefef46..a65aa7253 100644
--- a/elementary/config/config.py
+++ b/elementary/config/config.py
@@ -73,6 +73,7 @@ def __init__(
         env: str = DEFAULT_ENV,
         run_dbt_deps_if_needed: Optional[bool] = None,
         project_name: Optional[str] = None,
+        use_system_ca_files: bool = True,
     ):
         self.config_dir = config_dir
         self.profiles_dir = profiles_dir
@@ -204,6 +205,8 @@ def __init__(
             "disable_elementary_version_check", False
         )
 
+        self.use_system_ca_files = use_system_ca_files
+
     def _load_configuration(self) -> dict:
         if not os.path.exists(self.config_dir):
             os.makedirs(self.config_dir)
diff --git a/elementary/monitor/cli.py b/elementary/monitor/cli.py
index 019293f1f..f31357edf 100644
--- a/elementary/monitor/cli.py
+++ b/elementary/monitor/cli.py
@@ -73,6 +73,11 @@ def decorator(func):
                 default=None,
                 help="The Slack token for your workspace.",
             )(func)
+            func = click.option(
+                "--use-system-ca-files/--no-use-system-ca-files",
+                default=True,
+                help="Whether to use the system CA files for SSL connections or the ones provided by certify (see https://pypi.org/project/certifi).",
+            )(func)
         if cmd in (Command.REPORT, Command.SEND_REPORT):
             func = click.option(
                 "--exclude-elementary-models",
@@ -304,6 +309,7 @@ def monitor(
     report_url,
     filters,
     teams_webhook,
+    use_system_ca_files,
 ):
     """
     Get alerts on failures in dbt jobs.
@@ -335,6 +341,7 @@ def monitor(
         slack_group_alerts_by=group_by,
         report_url=report_url,
         teams_webhook=teams_webhook,
+        use_system_ca_files=use_system_ca_files,
     )
     anonymous_tracking = AnonymousCommandLineTracking(config)
     anonymous_tracking.set_env("use_select", bool(select))
@@ -652,6 +659,7 @@ def send_report(
     disable,
     include,
     target_path,
+    use_system_ca_files,
 ):
     """
     Generate and send the report to an external platform.
@@ -693,6 +701,7 @@ def send_report(
         report_url=report_url,
         env=env,
         project_name=project_name,
+        use_system_ca_files=use_system_ca_files,
     )
     anonymous_tracking = AnonymousCommandLineTracking(config)
     anonymous_tracking.set_env("use_select", bool(select))