diff --git a/castellum/appointments/management/commands/send_appointment_reminders.py b/castellum/appointments/management/commands/send_appointment_reminders.py
index eac18375f44d64a0af399091c79ca7efd0b1904e..e1ded801c8368f34ef40c76ea625b15326771aa1 100644
--- a/castellum/appointments/management/commands/send_appointment_reminders.py
+++ b/castellum/appointments/management/commands/send_appointment_reminders.py
@@ -46,7 +46,7 @@ def send_mail_to_subject(ctx, study, appointment):
     )
 
 
-def send_mail_to_study_conductors(study, not_reachable, base_url):
+def send_mail_to_study_conductors(study, not_reachable, base_url, ctx):
     urls = '\n'.join(
         base_url + reverse(
             'execution:participation-detail',
@@ -54,16 +54,15 @@ def send_mail_to_study_conductors(study, not_reachable, base_url):
         )
         for appointment in not_reachable
     )
-    with MailContext('internal') as ctx:
-        return ctx.send_mail(
-            settings.CASTELLUM_APPOINTMENT_NO_EMAIL_MAIL_SUBJECT.format(study=study),
-            (
-                lambda: {'urls': urls},
-                settings.CASTELLUM_APPOINTMENT_NO_EMAIL_MAIL_BODY,
-                settings.CASTELLUM_APPOINTMENT_NO_EMAIL_MAIL_BODY_EN,
-            ),
-            [user.email for user in study.conductors],
-        )
+    return ctx.send_mail(
+        settings.CASTELLUM_APPOINTMENT_NO_EMAIL_MAIL_SUBJECT.format(study=study),
+        (
+            lambda: {'urls': urls},
+            settings.CASTELLUM_APPOINTMENT_NO_EMAIL_MAIL_BODY,
+            settings.CASTELLUM_APPOINTMENT_NO_EMAIL_MAIL_BODY_EN,
+        ),
+        [user.email for user in study.conductors],
+    )
 
 
 def send_appointment_reminders(base_url):
@@ -71,17 +70,17 @@ def send_appointment_reminders(base_url):
     reached_count = 0
     not_reached_count = 0
 
-    for study in Study.objects.filter(status=Study.EXECUTION):
-        due_appointments = Appointment.objects.filter(
-            start__gte=now,
-            start__lte=now + settings.CASTELLUM_APPOINTMENT_REMINDER_PERIOD,
-            reminded=False,
-            session__study=study,
-            participation__status=Participation.INVITED,
-        ).select_related('participation__subject')
-        not_reachable = []
-
-        with MailContext('recruitment') as ctx:
+    with MailContext('recruitment') as ctx:
+        for study in Study.objects.filter(status=Study.EXECUTION):
+            due_appointments = Appointment.objects.filter(
+                start__gte=now,
+                start__lte=now + settings.CASTELLUM_APPOINTMENT_REMINDER_PERIOD,
+                reminded=False,
+                session__study=study,
+                participation__status=Participation.INVITED,
+            ).select_related('participation__subject')
+            not_reachable = []
+
             for appointment in due_appointments:
                 success = send_mail_to_subject(ctx, study, appointment)
                 if success:
@@ -90,10 +89,11 @@ def send_appointment_reminders(base_url):
                     not_reached_count += 1
                     not_reachable.append(appointment)
 
-        if not_reachable:
-            send_mail_to_study_conductors(study, not_reachable, base_url)
+            if not_reachable:
+                with MailContext('internal', ctx.connection) as internal_ctx:
+                    send_mail_to_study_conductors(study, not_reachable, base_url, internal_ctx)
 
-        due_appointments.update(reminded=True)
+                due_appointments.update(reminded=True)
 
     return reached_count, not_reached_count
 
diff --git a/castellum/utils/mail.py b/castellum/utils/mail.py
index 11c5f6df208539c0bad865e665e81f4b8e040117..d4be6ce9dd6a286046027cd15dbf12c999bd7219 100644
--- a/castellum/utils/mail.py
+++ b/castellum/utils/mail.py
@@ -41,8 +41,9 @@ def render_body_with_fallback(get_mail_data, text, fallback=None, lang=None):
 
 
 class MailContext:
-    def __init__(self, name=None):
-        self.connection = None
+    def __init__(self, name=None, connection=None):
+        self.connection = connection
+        self.close_connection = False
         self.data = {
             'from_email': settings.DEFAULT_FROM_EMAIL,
             'language': settings.LANGUAGE_CODE,
@@ -57,6 +58,7 @@ class MailContext:
     def __enter__(self):
         if not self.connection:
             self.connection = get_connection(**self.data['connection'])
+            self.close_connection = True
             try:
                 self.connection.open()
             except Exception:
@@ -66,7 +68,8 @@ class MailContext:
         return self
 
     def __exit__(self, type, value, traceback):
-        self.connection.close()
+        if self.close_connection:
+            self.connection.close()
         self.connection = None
 
     def prepare_body(self, body, recipients_string=''):