diff --git a/includes/controller/shifts_controller.php b/includes/controller/shifts_controller.php
index 726814cf..15f92a9d 100644
--- a/includes/controller/shifts_controller.php
+++ b/includes/controller/shifts_controller.php
@@ -221,6 +221,7 @@ function shift_delete_controller()
 
     // Schicht löschen bestätigt
     if ($request->hasPostData('delete')) {
+        UserWorkLog_from_shift($shift_id);
         Shift_delete($shift_id);
 
         engelsystem_log(
diff --git a/includes/mailer/shifts_mailer.php b/includes/mailer/shifts_mailer.php
index 37b26838..b496a007 100644
--- a/includes/mailer/shifts_mailer.php
+++ b/includes/mailer/shifts_mailer.php
@@ -94,7 +94,12 @@ function mail_shift_delete($shift)
     foreach ($users as $user) {
         $user = (new User())->forceFill($user);
         if ($user->settings->email_shiftinfo) {
-            engelsystem_email_to_user($user, __('Your Shift was deleted'), $message, true);
+            $userMessage = $message;
+            if ($shift['start'] < time() && !$user['freeloaded']) {
+                $userMessage .= "\n" . __('Since the deleted shift was already done, we added a worklog entry instead, to keep your work hours correct.') . "\n";
+            }
+
+            engelsystem_email_to_user($user, __('Your Shift was deleted'), $userMessage, true);
         }
     }
 }
diff --git a/includes/model/Shifts_model.php b/includes/model/Shifts_model.php
index 6bb17cf2..01295fbc 100644
--- a/includes/model/Shifts_model.php
+++ b/includes/model/Shifts_model.php
@@ -80,12 +80,15 @@ function Shifts_from_frab()
 }
 
 /**
- * @param array $room
+ * @param array|int $room
  * @return array[]
  */
 function Shifts_by_room($room)
 {
-    return DB::select('SELECT * FROM `Shifts` WHERE `RID`=? ORDER BY `start`', [$room['RID']]);
+    return DB::select(
+        'SELECT * FROM `Shifts` WHERE `RID`=? ORDER BY `start`',
+        [is_array($room) ? $room['RID'] : $room]
+    );
 }
 
 /**
@@ -508,8 +511,8 @@ function Shift_delete_by_psid($shift_psid)
  */
 function Shift_delete($shift_id)
 {
-    DB::delete('DELETE FROM `Shifts` WHERE `SID`=?', [$shift_id]);
     mail_shift_delete(Shift($shift_id));
+    DB::delete('DELETE FROM `Shifts` WHERE `SID`=?', [$shift_id]);
 }
 
 /**
diff --git a/includes/model/UserWorkLog_model.php b/includes/model/UserWorkLog_model.php
index 7b766c5e..cc7686cf 100644
--- a/includes/model/UserWorkLog_model.php
+++ b/includes/model/UserWorkLog_model.php
@@ -121,6 +121,56 @@ function UserWorkLog_create($userWorkLog)
     return $result;
 }
 
+/**
+ * @param array|int $shift
+ */
+function UserWorkLog_from_shift($shift)
+{
+    $shift = is_array($shift) ? $shift : Shift($shift);
+    $nightShifts = config('night_shifts');
+
+    if ($shift['start'] > time()) {
+        return;
+    }
+
+    $room = Room($shift['RID']);
+    foreach ($shift['ShiftEntry'] as $entry) {
+        if ($entry['freeloaded']) {
+            continue;
+        }
+
+        $type = AngelType($entry['TID']);
+
+        $nightShiftMultiplier = 1;
+        $shiftStart = Carbon::createFromTimestamp($shift['start']);
+        $shiftEnd = Carbon::createFromTimestamp($shift['end']);
+        if (
+            $nightShifts['enabled']
+            && (
+                $shiftStart->hour >= $nightShifts['start'] && $shiftStart->hour < $nightShifts['end']
+                || $shiftEnd->hour >= $nightShifts['start'] && $shiftEnd->hour < $nightShifts['end']
+            )
+        ) {
+            $nightShiftMultiplier = $nightShifts['multiplier'];
+        }
+
+        UserWorkLog_create([
+            'user_id'        => $entry['UID'],
+            'work_timestamp' => $shift['start'],
+            'work_hours'     => (($shift['end'] - $shift['start']) / 60 / 60) * $nightShiftMultiplier,
+            'comment'        => sprintf(
+                '%s (%s as %s) in %s, %s-%s',
+                $shift['name'],
+                $shift['title'],
+                $type['name'],
+                $room['Name'],
+                Carbon::createFromTimestamp($shift['start'])->format(__('m/d/Y h:i a')),
+                Carbon::createFromTimestamp($shift['end'])->format(__('m/d/Y h:i a'))
+            ),
+        ]);
+    }
+}
+
 /**
  * New user work log entry
  *
diff --git a/includes/pages/admin_rooms.php b/includes/pages/admin_rooms.php
index bc0eb651..c55eb227 100644
--- a/includes/pages/admin_rooms.php
+++ b/includes/pages/admin_rooms.php
@@ -179,9 +179,16 @@ function admin_rooms()
             ]);
         } elseif ($request->input('show') == 'delete') {
             if ($request->hasPostData('ack')) {
+                $shifts = Shifts_by_room($room_id);
+                foreach ($shifts as $shift) {
+                    $shift = Shift($shift['SID']);
+
+                    UserWorkLog_from_shift($shift);
+                    mail_shift_delete($shift);
+                }
+
                 Room_delete($room_id);
 
-                engelsystem_log('Room deleted: ' . $name);
                 success(sprintf(__('Room %s deleted.'), $name));
                 redirect(page_link_to('admin_rooms'));
             }
diff --git a/resources/lang/de_DE/default.po b/resources/lang/de_DE/default.po
index d6dc38bb..8dba9b4b 100644
--- a/resources/lang/de_DE/default.po
+++ b/resources/lang/de_DE/default.po
@@ -674,6 +674,9 @@ msgstr "Eine deiner Schichten wurde gelöscht:"
 msgid "Your Shift was deleted"
 msgstr "Deine Schicht wurde gelöscht"
 
+msgid "Since the deleted shift was already done, we added a worklog entry instead, to keep your work hours correct."
+msgstr "Da die gelöschte Schicht bereits vergangen ist, haben wir einen entsprechenden Arbeitseinsatz hinzugefügt."
+
 #: includes/mailer/shifts_mailer.php:114
 msgid "You have been assigned to a Shift:"
 msgstr "Du wurdest in eine Schicht eingetragen:"