diff --git a/elementary/clients/slack/client.py b/elementary/clients/slack/client.py
index f66a9b969..0c2814157 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, Union
 
+import certifi
 import requests
 from ratelimit import limits, sleep_and_retry
 from slack_sdk import WebClient, WebhookClient
@@ -25,8 +27,9 @@ 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] = {}
@@ -38,19 +41,38 @@ 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.")
+            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,
                 is_workflow=config.is_slack_workflow,
                 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):
@@ -85,12 +107,13 @@ 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)
@@ -231,16 +254,22 @@ def __init__(
         webhook: str,
         is_workflow: bool,
         tracking: Optional[Tracking] = None,
+        ssl_context: Optional[ssl.SSLContext] = None,
     ):
         self.webhook = webhook
         self.is_workflow = is_workflow
-        super().__init__(tracking)
+        super().__init__(tracking, ssl_context)
 
-    def _initial_client(self):
+    def _initial_client(self, ssl_context: Optional[ssl.SSLContext]):
         if self.is_workflow:
+            # Workflow webhooks do not support the ssl_context parameter.
+            # requests.Session() uses the requests default CA bundle (certifi).
             return requests.Session()
+
         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 b8e56143c..b15ff9c43 100644
--- a/elementary/config/config.py
+++ b/elementary/config/config.py
@@ -76,6 +76,7 @@ def __init__(
         run_dbt_deps_if_needed: Optional[bool] = None,
         project_name: Optional[str] = None,
         quiet_logs: Optional[bool] = None,
+        use_system_ca_files: bool = True,
     ):
         self.config_dir = config_dir
         self.profiles_dir = profiles_dir
@@ -223,6 +224,8 @@ def __init__(
             quiet_logs, config.get("quiet_logs"), 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 9b47133ff..0550b434b 100644
--- a/elementary/monitor/cli.py
+++ b/elementary/monitor/cli.py
@@ -75,6 +75,11 @@ 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",
@@ -331,6 +336,7 @@ def monitor(
     teams_webhook,
     maximum_columns_in_alert_samples,
     quiet_logs,
+    use_system_ca_files,
 ):
     """
     Get alerts on failures in dbt jobs.
@@ -365,6 +371,7 @@ def monitor(
         teams_webhook=teams_webhook,
         maximum_columns_in_alert_samples=maximum_columns_in_alert_samples,
         quiet_logs=quiet_logs,
+        use_system_ca_files=use_system_ca_files,
     )
     anonymous_tracking = AnonymousCommandLineTracking(config)
     anonymous_tracking.set_env("use_select", bool(select))
@@ -692,6 +699,7 @@ def send_report(
     include,
     target_path,
     quiet_logs,
+    use_system_ca_files,
 ):
     """
     Generate and send the report to an external platform.
@@ -735,6 +743,7 @@ def send_report(
         env=env,
         project_name=project_name,
         quiet_logs=quiet_logs,
+        use_system_ca_files=use_system_ca_files,
     )
     anonymous_tracking = AnonymousCommandLineTracking(config)
     anonymous_tracking.set_env("use_select", bool(select))