diff --git a/documentation/changelog.rst b/documentation/changelog.rst
index e64a74a3e..725b5ef5c 100644
--- a/documentation/changelog.rst
+++ b/documentation/changelog.rst
@@ -15,6 +15,7 @@ Infrastructure / Support
 ----------------------
 
 * Add possibility to send errors to Sentry [see `PR #143 <http://www.github.com/SeitaBV/flexmeasures/pull/143>`_]
+* Add CLI task to monitor if tasks ran successfully and recently enough [see `PR #146 <http://www.github.com/SeitaBV/flexmeasures/pull/146>`_]
 
 
 v0.5.0 | June 7, 2021
diff --git a/documentation/configuration.rst b/documentation/configuration.rst
index f000e8549..ba2af79a8 100644
--- a/documentation/configuration.rst
+++ b/documentation/configuration.rst
@@ -153,6 +153,15 @@ Token for accessing the MapBox API (for displaying maps on the dashboard and ass
 Default: ``None``
 
 
+SENTRY_SDN
+^^^^^^^^^^^^
+
+Set tokenized URL, so errors will be sent to Sentry when ``app.env`` is not in `debug` or `testing` mode.
+E.g.: ``https://<examplePublicKey>@o<something>.ingest.sentry.io/<project-Id>``
+
+Default: ``None``
+
+
 SQLAlchemy
 ----------
 
@@ -356,6 +365,13 @@ Token which external services can use to check on the status of recurring tasks
 Default: ``None``
 
 
+FLEXMEASURES_MONITORING_MAIL_RECIPIENTS
+^^^^^^^^^^^^^^^^^^^^^^^
+
+E-mail addresses to send monitoring alerts to from the CLI task ``flexmeasures monitor tasks``. For example ``["fred@one.com", "wilma@two.com"]``
+
+Default: ``[]``
+
 
 .. _redis-config:
 
diff --git a/flexmeasures/data/__init__.py b/flexmeasures/data/__init__.py
index 4ddf8e80c..c48e7c22e 100644
--- a/flexmeasures/data/__init__.py
+++ b/flexmeasures/data/__init__.py
@@ -26,6 +26,7 @@ def register_at(app: Flask):
         # Register some useful custom scripts with the flask cli
         with app.app_context():
             import flexmeasures.data.scripts.cli_tasks.jobs
+            import flexmeasures.data.scripts.cli_tasks.monitor
             import flexmeasures.data.scripts.cli_tasks.data_add
             import flexmeasures.data.scripts.cli_tasks.data_delete
             import flexmeasures.data.scripts.cli_tasks.db_ops
diff --git a/flexmeasures/data/scripts/cli_tasks/monitor.py b/flexmeasures/data/scripts/cli_tasks/monitor.py
new file mode 100644
index 000000000..896af9e1a
--- /dev/null
+++ b/flexmeasures/data/scripts/cli_tasks/monitor.py
@@ -0,0 +1,88 @@
+from datetime import timedelta
+from typing import Optional
+
+import click
+from flask import current_app as app
+from flask.cli import with_appcontext
+from flask_mail import Message
+from sentry_sdk import (
+    capture_message as capture_message_for_sentry,
+    set_context as set_sentry_context,
+)
+
+from flexmeasures.data.models.task_runs import LatestTaskRun
+from flexmeasures.utils.time_utils import server_now
+
+
+@click.group("monitor")
+def fm_monitor():
+    """FlexMeasures: Monitor tasks."""
+
+
+def send_monitoring_alert(
+    task_name: str, msg: str, latest_run: Optional[LatestTaskRun] = None
+):
+    """
+    Send any monitoring message per Sentry and per email. Also log an error.
+    """
+    latest_run_txt = ""
+    if latest_run:
+        set_sentry_context(
+            "latest_run", {"time": latest_run.datetime, "status": latest_run.status}
+        )
+        latest_run_txt = (
+            f"Last run was at {latest_run.datetime}, status was: {latest_run.status}"
+        )
+
+    capture_message_for_sentry(msg)
+
+    email_recipients = app.config.get("FLEXMEASURES_MONITORING_MAIL_RECIPIENTS", [])
+    if len(email_recipients) > 0:
+        email = Message(subject=f"Problem with task {task_name}", bcc=email_recipients)
+        email.body = f"{msg}\n\n{latest_run_txt}\nWe suggest to check the logs."
+        app.mail.send(email)
+
+    app.logger.error(f"{msg} {latest_run_txt}")
+
+
+@fm_monitor.command("tasks")
+@with_appcontext
+@click.option(
+    "--task",
+    type=(str, int),
+    multiple=True,
+    required=True,
+    help="The name of the task and the maximal allowed minutes between successful runs. Use multiple times if needed.",
+)
+def monitor_tasks(task):
+    """
+    Check if the given task's last successful execution happened less than the allowed time ago.
+    If not, alert someone, via email or sentry.
+    """
+    for t in task:
+        task_name = t[0]
+        app.logger.info(f"Checking latest run of task {task_name} ...")
+        latest_run: LatestTaskRun = LatestTaskRun.query.get(task_name)
+        if latest_run is None:
+            msg = f"Task {task_name} has no last run and thus cannot be monitored. Is it configured properly?"
+            send_monitoring_alert(task_name, msg)
+            return
+        now = server_now()
+        acceptable_interval = timedelta(minutes=t[1])
+        # check if latest run was recently enough
+        if latest_run.datetime >= now - acceptable_interval:
+            # latest run time is okay, let's check the status
+            if latest_run.status is False:
+                msg = f"A failure has been reported on task {task_name}."
+                send_monitoring_alert(task_name, msg, latest_run)
+        else:
+            msg = (
+                f"Task {task_name}'s latest run time is outside of the acceptable range "
+                f"({acceptable_interval})."
+            )
+            app.logger.error(msg)
+            send_monitoring_alert(task_name, msg, latest_run)
+    app.logger.info("Done checking task runs ...")
+
+
+app.cli.add_command(fm_monitor)
diff --git a/flexmeasures/utils/config_defaults.py b/flexmeasures/utils/config_defaults.py
index 70de7332a..199a42785 100644
--- a/flexmeasures/utils/config_defaults.py
+++ b/flexmeasures/utils/config_defaults.py
@@ -80,6 +80,7 @@ class Config(object):
     # traces_sample_rate is for performance monitoring across all transactions,
     # you probably want to adjust this.
     FLEXMEASURES_SENTRY_CONFIG: dict = dict(traces_sample_rate=0.33)
+    FLEXMEASURES_MONITORING_MAIL_RECIPIENTS: List[str] = []
 
     FLEXMEASURES_PLATFORM_NAME: str = "FlexMeasures"
     FLEXMEASURES_MODE: str = ""