diff --git a/index_parentPhotoDeleteProcess.php b/index_parentPhotoDeleteProcess.php
index 380c6655f8..0beff949b9 100644
--- a/index_parentPhotoDeleteProcess.php
+++ b/index_parentPhotoDeleteProcess.php
@@ -21,6 +21,7 @@
 
 //Gibbon system-wide includes
 
+use Gibbon\Contracts\Filesystem\FileHandler;
 use Gibbon\Http\Url;
 
 include './gibbon.php';
@@ -47,6 +48,8 @@
         header("Location: {$URL->withReturn('error2')}");
     } else {
         //UPDATE
+        $fileDeleted = $container->get(FileHandler::class)->deleteFile('gibbonPerson', $gibbonPersonID, 'image_240');
+
         try {
             $data = array('gibbonPersonID' => $gibbonPersonID);
             $sql = "UPDATE gibbonPerson SET image_240='' WHERE gibbonPersonID=:gibbonPersonID";
diff --git a/modules/Activities/activities_categories_deleteProcess.php b/modules/Activities/activities_categories_deleteProcess.php
index 110d59c6d3..43cf84356d 100755
--- a/modules/Activities/activities_categories_deleteProcess.php
+++ b/modules/Activities/activities_categories_deleteProcess.php
@@ -17,6 +17,7 @@
 along with this program. If not, see <http://www.gnu.org/licenses/>.
 */
 
+use Gibbon\Contracts\Filesystem\FileHandler;
 use Gibbon\Data\Validator;
 use Gibbon\Domain\Activities\ActivityCategoryGateway;
 
@@ -51,6 +52,10 @@
 
     $deleted = $categoryGateway->delete($gibbonActivityCategoryID);
 
+    if ($deleted) {
+        $fileDeleted = $container->get(FileHandler::class)->deleteFile('gibbonActivityCategory', $gibbonActivityCategoryID, 'backgroundImage');
+    }
+
     $URL .= !$deleted
         ? '&return=error2'
         : '&return=success0';
diff --git a/modules/Activities/activities_manage_deleteProcess.php b/modules/Activities/activities_manage_deleteProcess.php
index 183137321e..6eda7df842 100644
--- a/modules/Activities/activities_manage_deleteProcess.php
+++ b/modules/Activities/activities_manage_deleteProcess.php
@@ -19,6 +19,9 @@
 along with this program. If not, see <http://www.gnu.org/licenses/>.
 */
 
+use Gibbon\Contracts\Filesystem\FileHandler;
+use Gibbon\Domain\Activities\ActivityPhotoGateway;
+
 include '../../gibbon.php';
 
 $gibbonActivityID = $_POST['gibbonActivityID']  ?? '';
@@ -50,6 +53,13 @@
             $URL .= '&return=error2';
             header("Location: {$URL}");
         } else {
+            // Delete file attachments for all activity photos before deleting the activity
+            $activityPhotos = $container->get(ActivityPhotoGateway::class)->selectBy(['gibbonActivityID' => $gibbonActivityID], ['gibbonActivityPhotoID'])->fetchAll();
+            
+            foreach ($activityPhotos as $photo) {
+                $photoDeleted = $container->get(FileHandler::class)->deleteFile('gibbonActivityPhoto', $photo['gibbonActivityPhotoID'], 'filePath');
+            }
+
             //Write to database
             try {
                 $data = array('gibbonActivityID' => $gibbonActivityID);
diff --git a/modules/Data Updater/data_medical_manage_deleteProcess.php b/modules/Data Updater/data_medical_manage_deleteProcess.php
index 77c15bcb48..5c8672e5b9 100644
--- a/modules/Data Updater/data_medical_manage_deleteProcess.php	
+++ b/modules/Data Updater/data_medical_manage_deleteProcess.php	
@@ -19,6 +19,9 @@
 along with this program. If not, see <http://www.gnu.org/licenses/>.
 */
 
+use Gibbon\Contracts\Filesystem\FileHandler;
+use Gibbon\Domain\DataUpdater\MedicalConditionUpdateGateway;
+
 include '../../gibbon.php';
 
 $gibbonSchoolYearID = $_POST['gibbonSchoolYearID'] ?? $session->get('gibbonSchoolYearID');
@@ -51,6 +54,9 @@
             $URL .= '&return=error2';
             header("Location: {$URL}");
         } else {
+            // Fetch child condition update IDs before deleting the parent record
+            $conditionUpdates = $container->get(MedicalConditionUpdateGateway::class)->selectBy(['gibbonPersonMedicalUpdateID' => $gibbonPersonMedicalUpdateID], ['gibbonPersonMedicalConditionUpdateID'])->fetchAll();
+
             //Write to database
             try {
                 $data = array('gibbonPersonMedicalUpdateID' => $gibbonPersonMedicalUpdateID);
@@ -62,6 +68,11 @@
                 header("Location: {$URL}");
                 exit();
             }
+            
+            // Delete file attachments for all condition updates linked to this medical update
+            foreach ($conditionUpdates as $conditionUpdate) {
+                $fileDeleted = $container->get(FileHandler::class)->deleteFile('gibbonPersonMedicalConditionUpdate', $conditionUpdate['gibbonPersonMedicalConditionUpdateID'], 'attachment');
+            }
 
             $URLDelete = $URLDelete.'&return=success0';
             header("Location: {$URLDelete}");
diff --git a/modules/Departments/department_edit_resource_deleteProcess.php b/modules/Departments/department_edit_resource_deleteProcess.php
index 675648820f..99f44d65ff 100644
--- a/modules/Departments/department_edit_resource_deleteProcess.php
+++ b/modules/Departments/department_edit_resource_deleteProcess.php
@@ -19,6 +19,7 @@
 along with this program. If not, see <http://www.gnu.org/licenses/>.
 */
 
+use Gibbon\Contracts\Filesystem\FileHandler;
 use Gibbon\Domain\Departments\DepartmentResourceGateway;
 
 include '../../gibbon.php';
@@ -73,6 +74,8 @@
                     exit();
                 }
 
+                $fileDeleted = $container->get(FileHandler::class)->deleteFile('gibbonDepartmentResource', $gibbonDepartmentResourceID, 'url');
+
                 $URL .= '&return=success0';
                 header("Location: {$URL}");
             }
diff --git a/modules/Formal Assessment/externalAssessment_manage_details_deleteProcess.php b/modules/Formal Assessment/externalAssessment_manage_details_deleteProcess.php
index dfe5bd5c0b..1bbfc4b64d 100644
--- a/modules/Formal Assessment/externalAssessment_manage_details_deleteProcess.php	
+++ b/modules/Formal Assessment/externalAssessment_manage_details_deleteProcess.php	
@@ -1,6 +1,4 @@
 <?php
-
-use Gibbon\Domain\FormalAssessment\ExternalAssessmentStudentGateway;
 /*
 Gibbon: the flexible, open school platform
 Founded by Ross Parker at ICHK Secondary. Built by Ross Parker, Sandra Kuipers and the Gibbon community (https://gibbonedu.org/about/)
@@ -21,6 +19,9 @@
 along with this program. If not, see <http://www.gnu.org/licenses/>.
 */
 
+use Gibbon\Contracts\Filesystem\FileHandler;
+use Gibbon\Domain\FormalAssessment\ExternalAssessmentStudentGateway;
+
 include '../../gibbon.php';
 
 $gibbonExternalAssessmentStudentID = $_POST['gibbonExternalAssessmentStudentID'] ?? '';
@@ -80,6 +81,8 @@
                     exit();
                 }
 
+                $fileDeleted = $container->get(FileHandler::class)->deleteFile('gibbonExternalAssessmentStudent', $gibbonExternalAssessmentStudentID, 'attachment');
+
                 $URLDelete = $URLDelete.'&return=success0';
                 header("Location: {$URLDelete}");
             }
diff --git a/modules/Formal Assessment/internalAssessment_manage_deleteProcess.php b/modules/Formal Assessment/internalAssessment_manage_deleteProcess.php
index f8389014c4..b4134a8dbb 100644
--- a/modules/Formal Assessment/internalAssessment_manage_deleteProcess.php	
+++ b/modules/Formal Assessment/internalAssessment_manage_deleteProcess.php	
@@ -19,6 +19,7 @@
 along with this program. If not, see <http://www.gnu.org/licenses/>.
 */
 
+use Gibbon\Contracts\Filesystem\FileHandler;
 use Gibbon\Domain\FormalAssessment\InternalAssessmentColumnGateway;
 
 include '../../gibbon.php';
@@ -57,6 +58,8 @@
                 exit();
             }
 
+            $fileDeleted = $container->get(FileHandler::class)->deleteFile('gibbonInternalAssessmentColumn', $gibbonInternalAssessmentColumnID, 'attachment');
+
             $URLDelete = $URLDelete.'&return=success0';
             header("Location: {$URLDelete}");
         }
diff --git a/modules/Formal Assessment/internalAssessment_write_data_responseDeleteProcess.php b/modules/Formal Assessment/internalAssessment_write_data_responseDeleteProcess.php
index e817ab126d..fbe3bebca9 100644
--- a/modules/Formal Assessment/internalAssessment_write_data_responseDeleteProcess.php	
+++ b/modules/Formal Assessment/internalAssessment_write_data_responseDeleteProcess.php	
@@ -20,6 +20,8 @@
 */
 
 use Gibbon\Data\Validator;
+use Gibbon\Domain\FormalAssessment\InternalAssessmentEntryGateway;
+use Gibbon\Contracts\Filesystem\FileHandler;
 
 require_once '../../gibbon.php';
 
@@ -55,6 +57,13 @@
         }
 
         $URL .= '&return=success0';
+
+        $entryRow = $container->get(InternalAssessmentEntryGateway::class)->selectBy(['gibbonPersonIDStudent' => $gibbonPersonID, 'gibbonInternalAssessmentColumnID' => $gibbonInternalAssessmentColumnID], ['gibbonInternalAssessmentEntryID'])->fetch();
+
+        if (!empty($entryRow)) {
+            $fileDeleted = $container->get(FileHandler::class)->deleteFile('gibbonInternalAssessmentEntry', $entryRow['gibbonInternalAssessmentEntryID'], 'response');
+        }
+
         //Success 0
         header("Location: {$URL}");
     }
diff --git a/modules/Library/library_manage_catalog_deleteProcess.php b/modules/Library/library_manage_catalog_deleteProcess.php
index d3a4d3b09e..48cf28ea8b 100644
--- a/modules/Library/library_manage_catalog_deleteProcess.php
+++ b/modules/Library/library_manage_catalog_deleteProcess.php
@@ -19,6 +19,8 @@
 along with this program. If not, see <http://www.gnu.org/licenses/>.
 */
 
+use Gibbon\Contracts\Filesystem\FileHandler;
+
 include '../../gibbon.php';
 
 include './moduleFunctions.php';
@@ -57,6 +59,8 @@
         }
 
         //Success 0
+        $fileDeleted = $container->get(FileHandler::class)->deleteFile('gibbonLibraryItem', $queryArr['gibbonLibraryItemID'], 'imageLocation');
+
         $queryArr['q'] = "/modules/".getModuleName($_POST['address'])."/library_manage_catalog.php";
         $queryArr['return'] = "success0";
         header("Location: " . $baseURL . http_build_query($queryArr));
diff --git a/modules/Markbook/markbook_edit_data_responseDeleteProcess.php b/modules/Markbook/markbook_edit_data_responseDeleteProcess.php
index ea74e906ce..96267ff480 100644
--- a/modules/Markbook/markbook_edit_data_responseDeleteProcess.php
+++ b/modules/Markbook/markbook_edit_data_responseDeleteProcess.php
@@ -19,7 +19,9 @@
 along with this program. If not, see <http://www.gnu.org/licenses/>.
 */
 
+use Gibbon\Contracts\Filesystem\FileHandler;
 use Gibbon\Data\Validator;
+use Gibbon\Domain\Markbook\MarkbookEntryGateway;
 
 require_once '../../gibbon.php';
 
@@ -55,6 +57,14 @@
         }
 
         $URL .= '&return=success0';
+
+        // Delete the file attachment for this entry response
+        $entryRow = $container->get(MarkbookEntryGateway::class)->selectBy(['gibbonPersonIDStudent' => $gibbonPersonID, 'gibbonMarkbookColumnID' => $gibbonMarkbookColumnID], ['gibbonMarkbookEntryID'])->fetch();
+        
+        if (!empty($entryRow)) {
+            $fileDeleted = $container->get(FileHandler::class)->deleteFile('gibbonMarkbookEntry', $entryRow['gibbonMarkbookEntryID'], 'response');
+        }
+
         //Success 0
         header("Location: {$URL}");
     }
diff --git a/modules/Markbook/markbook_edit_deleteProcess.php b/modules/Markbook/markbook_edit_deleteProcess.php
index 33398420df..1afa0c15b7 100644
--- a/modules/Markbook/markbook_edit_deleteProcess.php
+++ b/modules/Markbook/markbook_edit_deleteProcess.php
@@ -19,6 +19,9 @@
 along with this program. If not, see <http://www.gnu.org/licenses/>.
 */
 
+use Gibbon\Contracts\Filesystem\FileHandler;
+use Gibbon\Domain\Markbook\MarkbookEntryGateway;
+
 include '../../gibbon.php';
 
 $gibbonCourseClassID = $_POST['gibbonCourseClassID'] ?? '';
@@ -64,6 +67,15 @@
                 exit();
             }
 
+            // Delete file attachments for all markbook entry responses for this column
+            $entryRows = $container->get(MarkbookEntryGateway::class)->selectBy(['gibbonMarkbookColumnID' => $gibbonMarkbookColumnID], ['gibbonMarkbookEntryID'])->fetchAll();
+        
+            foreach ($entryRows as $entryRow) {
+                $entryFileDeleted = $container->get(FileHandler::class)->deleteFile('gibbonMarkbookEntry', $entryRow['gibbonMarkbookEntryID'], 'response');
+            }
+            
+            $columnFileDeleted = $container->get(FileHandler::class)->deleteFile('gibbonMarkbookColumn', $gibbonMarkbookColumnID, 'attachment');
+
             $URLDelete = $URLDelete.'&return=success0';
             header("Location: {$URLDelete}");
         }
diff --git a/modules/Planner/planner_deleteProcess.php b/modules/Planner/planner_deleteProcess.php
index 5e91bd1ced..ee3bf5ddae 100644
--- a/modules/Planner/planner_deleteProcess.php
+++ b/modules/Planner/planner_deleteProcess.php
@@ -19,6 +19,9 @@
 along with this program. If not, see <http://www.gnu.org/licenses/>.
 */
 
+use Gibbon\Contracts\Filesystem\FileHandler;
+use Gibbon\Domain\Planner\PlannerEntryHomeworkGateway;
+
 include '../../gibbon.php';
 
 $gibbonPlannerEntryID = $_POST['gibbonPlannerEntryID'] ?? '';
@@ -85,7 +88,15 @@
                 $URL .= "&return=error2$params";
                 header("Location: {$URL}");
             } else {
-                //Write to database
+                //Write to database          
+
+                // Delete file attachments for all homework entries before deleting the planner entry
+                $homeworkRows = $container->get(PlannerEntryHomeworkGateway::class)->selectBy(['gibbonPlannerEntryID' => $gibbonPlannerEntryID], ['gibbonPlannerEntryHomeworkID'])->fetchAll();
+
+                foreach ($homeworkRows as $homework) {
+                    $homeWorkFileDeleted = $container->get(FileHandler::class)->deleteFile('gibbonPlannerEntryHomework', $homework['gibbonPlannerEntryHomeworkID'], 'location');
+                }
+                
                 try {
                     $data = array('gibbonPlannerEntryID' => $gibbonPlannerEntryID);
                     $sql = 'DELETE FROM gibbonPlannerEntryOutcome WHERE gibbonPlannerEntryID=:gibbonPlannerEntryID';
diff --git a/modules/Planner/planner_view_full_submit_deleteProcess.php b/modules/Planner/planner_view_full_submit_deleteProcess.php
index a29f9b89b4..b1190fa73f 100644
--- a/modules/Planner/planner_view_full_submit_deleteProcess.php
+++ b/modules/Planner/planner_view_full_submit_deleteProcess.php
@@ -19,6 +19,8 @@
 along with this program. If not, see <http://www.gnu.org/licenses/>.
 */
 
+use Gibbon\Contracts\Filesystem\FileHandler;
+
 //Gibbon system-wide includes
 include '../../gibbon.php';
 
@@ -71,6 +73,8 @@
                 exit();
             }
 
+            $fileDeleted = $container->get(FileHandler::class)->deleteFile('gibbonPlannerEntryHomework', $gibbonPlannerEntryHomeworkID, 'location');
+
             $URL .= '&return=success0';
             header("Location: {$URL}");
         }
diff --git a/modules/Planner/planner_view_full_submit_studentDeleteProcess.php b/modules/Planner/planner_view_full_submit_studentDeleteProcess.php
index 69b4f8a957..84e724b748 100644
--- a/modules/Planner/planner_view_full_submit_studentDeleteProcess.php
+++ b/modules/Planner/planner_view_full_submit_studentDeleteProcess.php
@@ -19,6 +19,7 @@
 along with this program. If not, see <http://www.gnu.org/licenses/>.
 */
 
+use Gibbon\Contracts\Filesystem\FileHandler;
 use Gibbon\Data\Validator;
 
 require_once '../../gibbon.php';
@@ -74,6 +75,8 @@
                 exit();
             }
 
+            $fileDeleted = $container->get(FileHandler::class)->deleteFile('gibbonPlannerEntryHomework', $gibbonPlannerEntryHomeworkID, 'location');
+
             $URL .= '&return=success0';
             header("Location: {$URL}");
         }
diff --git a/modules/Planner/units_deleteProcess.php b/modules/Planner/units_deleteProcess.php
index 7e5465a024..4da4f92e0c 100644
--- a/modules/Planner/units_deleteProcess.php
+++ b/modules/Planner/units_deleteProcess.php
@@ -19,6 +19,7 @@
 along with this program. If not, see <http://www.gnu.org/licenses/>.
 */
 
+use Gibbon\Contracts\Filesystem\FileHandler;
 use Gibbon\Domain\Timetable\CourseGateway;
 
 include '../../gibbon.php';
@@ -111,6 +112,8 @@
                         header("Location: {$URL}");
                         exit();
                     }
+                    
+                    $fileDeleted = $container->get(FileHandler::class)->deleteFile('gibbonUnit', $gibbonUnitID, 'attachment');
 
                     $URLDelete = $URLDelete.'&return=success0';
                     header("Location: {$URLDelete}");
diff --git a/modules/Reports/archive_manage_deleteProcess.php b/modules/Reports/archive_manage_deleteProcess.php
index ff05c66c02..5531029d91 100644
--- a/modules/Reports/archive_manage_deleteProcess.php
+++ b/modules/Reports/archive_manage_deleteProcess.php
@@ -19,7 +19,9 @@
 along with this program. If not, see <http://www.gnu.org/licenses/>.
 */
 
+use Gibbon\Contracts\Filesystem\FileHandler;
 use Gibbon\Module\Reports\Domain\ReportArchiveGateway;
+use Gibbon\Module\Reports\Domain\ReportArchiveEntryGateway;
 
 require_once '../../gibbon.php';
 
@@ -48,6 +50,13 @@
         exit;
     }
 
+    // Delete file attachments for all entries in this archive before deleting the archive
+    $archiveEntries = $container->get(ReportArchiveEntryGateway::class)->selectBy(['gibbonReportArchiveID' => $gibbonReportArchiveID], ['gibbonReportArchiveEntryID'])->fetchAll();
+
+    foreach ($archiveEntries as $entry) {
+        $fileDeleted = $container->get(FileHandler::class)->deleteFile('gibbonReportArchiveEntry', $entry['gibbonReportArchiveEntryID'], 'filePath');
+    }
+
     $deleted = $reportArchiveGateway->delete($gibbonReportArchiveID);
     $partialFail &= !$deleted;
 
diff --git a/modules/Reports/templates_manage_section_deleteProcess.php b/modules/Reports/templates_manage_section_deleteProcess.php
index 65e3c97a8c..1d63f0cde9 100644
--- a/modules/Reports/templates_manage_section_deleteProcess.php
+++ b/modules/Reports/templates_manage_section_deleteProcess.php
@@ -19,6 +19,8 @@
 along with this program. If not, see <http://www.gnu.org/licenses/>.
 */
 
+use Gibbon\Contracts\Filesystem\FileHandler;
+use Gibbon\Domain\System\FilePointerGateway;
 use Gibbon\Module\Reports\Domain\ReportTemplateGateway;
 use Gibbon\Module\Reports\Domain\ReportTemplateSectionGateway;
 
@@ -53,6 +55,13 @@
         exit;
     }
 
+    // Delete any file attachments associated with this section (dynamic config columns)
+    $pointers = $container->get(FilePointerGateway::class)->selectBy(['foreignTable' => 'gibbonReportTemplateSection', 'foreignTableID' => $gibbonReportTemplateSectionID])->fetchAll();
+
+    foreach ($pointers as $pointer) {
+        $fileDeleted = $container->get(FileHandler::class)->deleteFile($pointer['foreignTable'], $pointer['foreignTableID'], $pointer['foreignColumn']);
+    }
+    
     $deleted = $templateSectionGateway->delete($gibbonReportTemplateSectionID);
 
     $URL .= !$deleted
diff --git a/modules/School Admin/department_manage_deleteProcess.php b/modules/School Admin/department_manage_deleteProcess.php
index bbc052e2a0..1a24e4c9a6 100644
--- a/modules/School Admin/department_manage_deleteProcess.php	
+++ b/modules/School Admin/department_manage_deleteProcess.php	
@@ -19,6 +19,9 @@
 along with this program. If not, see <http://www.gnu.org/licenses/>.
 */
 
+use Gibbon\Contracts\Filesystem\FileHandler;
+use Gibbon\Domain\Departments\DepartmentResourceGateway;
+
 include '../../gibbon.php';
 
 $gibbonDepartmentID = $_POST['gibbonDepartmentID'] ?? '';
@@ -72,6 +75,19 @@
                 exit();
             }
 
+            // Delete related department resources and files
+            $fileHandler = $container->get(FileHandler::class); 
+            $departmentResourceGateway = $container->get(DepartmentResourceGateway::class);             
+            $resourceResult = $departmentResourceGateway->selectBy(['gibbonDepartmentID' => $gibbonDepartmentID, 'type' => 'File'], ['gibbonDepartmentResourceID'])->fetchAll();
+
+            foreach ($resourceResult as $resource) {
+                $resourceDeleted = $fileHandler->deleteFile('gibbonDepartmentResource', $resource['gibbonDepartmentResourceID'], 'url');
+            }
+            
+            $deleted = $departmentResourceGateway->deleteWhere(['gibbonDepartmentID' => $gibbonDepartmentID]);          
+             
+            $fileDeleted = $fileHandler->deleteFile('gibbonDepartment', $gibbonDepartmentID, 'logo');
+
             $URLDelete = $URLDelete.'&return=success0';
             header("Location: {$URLDelete}");
         }
diff --git a/modules/School Admin/house_manage_deleteProcess.php b/modules/School Admin/house_manage_deleteProcess.php
index 90f51c1d50..2330aec981 100644
--- a/modules/School Admin/house_manage_deleteProcess.php	
+++ b/modules/School Admin/house_manage_deleteProcess.php	
@@ -19,6 +19,8 @@
 along with this program. If not, see <http://www.gnu.org/licenses/>.
 */
 
+use Gibbon\Contracts\Filesystem\FileHandler;
+
 include '../../gibbon.php';
 
 $gibbonHouseID = $_POST['gibbonHouseID'] ?? '';
@@ -62,6 +64,8 @@
                 exit();
             }
 
+            $fileDeleted = $container->get(FileHandler::class)->deleteFile('gibbonHouse', $gibbonHouseID, 'logo');
+
             $URLDelete = $URLDelete.'&return=success0';
             header("Location: {$URLDelete}");
         }
diff --git a/modules/Staff/applicationForm_manage_deleteProcess.php b/modules/Staff/applicationForm_manage_deleteProcess.php
index 5f5935cf31..be0b57d7ae 100644
--- a/modules/Staff/applicationForm_manage_deleteProcess.php
+++ b/modules/Staff/applicationForm_manage_deleteProcess.php
@@ -19,6 +19,8 @@
 along with this program. If not, see <http://www.gnu.org/licenses/>.
 */
 
+use Gibbon\Contracts\Filesystem\FileHandler;
+use Gibbon\Domain\Staff\StaffApplicationFormFileGateway;
 use Gibbon\Domain\User\PersonalDocumentGateway;
 
 include '../../gibbon.php';
@@ -63,6 +65,13 @@
                 exit();
             }
 
+            // Delete file attachments for all staff application form files
+            $staffAppFiles = $container->get(StaffApplicationFormFileGateway::class)->selectBy(['gibbonStaffApplicationFormID' => $gibbonStaffApplicationFormID], ['gibbonStaffApplicationFormFileID'])->fetchAll();
+
+            foreach ($staffAppFiles as $staffAppFile) {
+                $fileDeleted = $container->get(FileHandler::class)->deleteFile('gibbonStaffApplicationFormFile', $staffAppFile['gibbonStaffApplicationFormFileID'], 'path');
+            }
+
             //Delete files, but don't return error if it fails
             $data = array('gibbonStaffApplicationFormID' => $gibbonStaffApplicationFormID);
             $sql = 'DELETE FROM gibbonStaffApplicationFormFile WHERE gibbonStaffApplicationFormID=:gibbonStaffApplicationFormID';
diff --git a/modules/Staff/coverage_manage_deleteProcess.php b/modules/Staff/coverage_manage_deleteProcess.php
index a7a18aacf0..a20307761d 100644
--- a/modules/Staff/coverage_manage_deleteProcess.php
+++ b/modules/Staff/coverage_manage_deleteProcess.php
@@ -19,6 +19,7 @@
 along with this program. If not, see <http://www.gnu.org/licenses/>.
 */
 
+use Gibbon\Contracts\Filesystem\FileHandler;
 use Gibbon\Domain\Staff\StaffCoverageGateway;
 use Gibbon\Domain\Staff\StaffCoverageDateGateway;
 use Gibbon\Domain\Staff\StaffAbsenceGateway;
@@ -61,6 +62,8 @@
     // Then delete the coverage itself
     $partialFail &= !$staffCoverageGateway->delete($gibbonStaffCoverageID);
 
+    $fileDeleted = $container->get(FileHandler::class)->deleteFile('gibbonStaffCoverage', $gibbonStaffCoverageID, 'attachmentContent');
+
     // Check for other coverage linked to this absence
     $otherCoverage = $staffCoverageGateway->selectBy(['gibbonStaffAbsenceID' => $values['gibbonStaffAbsenceID']])->fetchAll();
 
diff --git a/modules/Students/applicationForm_manage_deleteProcess.php b/modules/Students/applicationForm_manage_deleteProcess.php
index 073363a115..a6a7d248a0 100644
--- a/modules/Students/applicationForm_manage_deleteProcess.php
+++ b/modules/Students/applicationForm_manage_deleteProcess.php
@@ -19,6 +19,8 @@
 along with this program. If not, see <http://www.gnu.org/licenses/>.
 */
 
+use Gibbon\Contracts\Filesystem\FileHandler;
+use Gibbon\Domain\Students\ApplicationFormFileGateway;
 use Gibbon\Domain\System\LogGateway;
 use Gibbon\Domain\User\PersonalDocumentGateway;
 
@@ -68,7 +70,7 @@
                 exit();
             }
 
-            //Attempt to write logo
+            //Attempt to write log
             $logGateway->addLog($session->get('gibbonSchoolYearIDCurrent'), 'Students', $session->get('gibbonPersonID'), 'Application Form - Delete', array('gibbonApplicationFormID' => $gibbonApplicationFormID, 'applicationFormContents' => serialize($row)), $_SERVER['REMOTE_ADDR']);
 
 
@@ -102,6 +104,19 @@
             $personalDocumentGateway->deletePersonalDocuments('gibbonApplicationFormParent1', $gibbonApplicationFormID);
             $personalDocumentGateway->deletePersonalDocuments('gibbonApplicationFormParent2', $gibbonApplicationFormID);
 
+            // Delete file attachments for all application form files
+            $appFiles = $container->get(ApplicationFormFileGateway::class)->selectBy(['gibbonApplicationFormID' => $gibbonApplicationFormID], ['gibbonApplicationFormFileID'])->fetchAll();
+
+            foreach ($appFiles as $appFile) {
+                $fileDeleted = $container->get(FileHandler::class)->deleteFile('gibbonApplicationFormFile', $appFile['gibbonApplicationFormFileID'], 'path');
+            }
+
+            //Delete files, but don't return error if it fails
+            $data = ['gibbonApplicationFormID' => $gibbonApplicationFormID];
+            $sql = 'DELETE FROM gibbonApplicationFormFile WHERE gibbonApplicationFormID=:gibbonApplicationFormID';
+            $result = $connection2->prepare($sql);
+            $result->execute($data);
+
             $URLDelete = $URLDelete.'&return=success0';
             header("Location: {$URLDelete}");
         }
diff --git a/modules/Students/medicalForm_manage_condition_deleteProcess.php b/modules/Students/medicalForm_manage_condition_deleteProcess.php
index 75fd0812d9..21733ca1fd 100644
--- a/modules/Students/medicalForm_manage_condition_deleteProcess.php
+++ b/modules/Students/medicalForm_manage_condition_deleteProcess.php
@@ -19,6 +19,8 @@
 along with this program. If not, see <http://www.gnu.org/licenses/>.
 */
 
+use Gibbon\Contracts\Filesystem\FileHandler;
+
 include '../../gibbon.php';
 
 //Check if gibbonPersonMedicalID and gibbonPersonMedicalConditionID specified
@@ -67,6 +69,8 @@
                     exit();
                 }
 
+                $fileDeleted = $container->get(FileHandler::class)->deleteFile('gibbonPersonMedicalCondition', $gibbonPersonMedicalConditionID, 'attachment');
+
                 $URLDelete = $URLDelete.'&return=success0';
                 header("Location: {$URLDelete}");
             }
diff --git a/modules/User Admin/user_manage_deleteProcess.php b/modules/User Admin/user_manage_deleteProcess.php
index 1f83e5458d..7978cb321f 100644
--- a/modules/User Admin/user_manage_deleteProcess.php	
+++ b/modules/User Admin/user_manage_deleteProcess.php	
@@ -19,6 +19,7 @@
 along with this program. If not, see <http://www.gnu.org/licenses/>.
 */
 
+use Gibbon\Contracts\Filesystem\FileHandler;
 use Gibbon\Domain\User\PersonalDocumentGateway;
 
 include '../../gibbon.php';
@@ -67,6 +68,8 @@
             // Personal Documents
             $container->get(PersonalDocumentGateway::class)->deletePersonalDocuments('gibbonPerson', $gibbonPersonID);
 
+            $fileDeleted = $container->get(FileHandler::class)->deleteFile('gibbonPerson', $gibbonPersonID, 'image_240');
+
             $URLDelete = $URLDelete.'&return=success0';
             header("Location: {$URLDelete}");
         }
diff --git a/src/Domain/FormalAssessment/InternalAssessmentEntryGateway.php b/src/Domain/FormalAssessment/InternalAssessmentEntryGateway.php
new file mode 100644
index 0000000000..f2fd9d0ace
--- /dev/null
+++ b/src/Domain/FormalAssessment/InternalAssessmentEntryGateway.php
@@ -0,0 +1,41 @@
+<?php
+/*
+Gibbon: the flexible, open school platform
+Founded by Ross Parker at ICHK Secondary. Built by Ross Parker, Sandra Kuipers and the Gibbon community (https://gibbonedu.org/about/)
+Copyright © 2010, Gibbon Foundation
+Gibbon™, Gibbon Education Ltd. (Hong Kong)
+
+This program is free software: you can redistribute it and/or modify
+it under the terms of the GNU General Public License as published by
+the Free Software Foundation, either version 3 of the License, or
+(at your option) any later version.
+
+This program is distributed in the hope that it will be useful,
+but WITHOUT ANY WARRANTY; without even the implied warranty of
+MERCHANTABILITY or FITNESS FOR A PARTICULAR PURPOSE. See the
+GNU General Public License for more details.
+
+You should have received a copy of the GNU General Public License
+along with this program. If not, see <http://www.gnu.org/licenses/>.
+*/
+
+namespace Gibbon\Domain\FormalAssessment;
+
+use Gibbon\Domain\Traits\TableAware;
+use Gibbon\Domain\QueryCriteria;
+use Gibbon\Domain\QueryableGateway;
+
+/**
+ * @version v31
+ * @since   v31
+ */
+class InternalAssessmentEntryGateway extends QueryableGateway
+{
+    use TableAware;
+
+    private static $tableName = 'gibbonInternalAssessmentEntry';
+    private static $primaryKey = 'gibbonInternalAssessmentEntryID';
+
+    private static $searchableColumns = [];
+    
+}
diff --git a/src/Domain/Staff/StaffApplicationFormFileGateway.php b/src/Domain/Staff/StaffApplicationFormFileGateway.php
index 48f8981f22..a7e14ea3b2 100644
--- a/src/Domain/Staff/StaffApplicationFormFileGateway.php
+++ b/src/Domain/Staff/StaffApplicationFormFileGateway.php
@@ -21,6 +21,8 @@
 
 namespace Gibbon\Domain\Staff;
 
+use Gibbon\Contracts\Database\Connection;
+use Gibbon\Contracts\Filesystem\FileHandler;
 use Gibbon\Domain\QueryCriteria;
 use Gibbon\Domain\QueryableGateway;
 use Gibbon\Domain\ScrubbableGateway;
@@ -47,4 +49,15 @@ class StaffApplicationFormFileGateway extends QueryableGateway implements Scrubb
     
     private static $scrubbableKey = ['timestamp', 'gibbonStaffApplicationForm', 'gibbonStaffApplicationFormID'];
     private static $scrubbableColumns = ['path' => 'deleteFile'];
+
+    /**
+     * @var FileHandler
+     */
+    private $fileHandler;
+
+    public function __construct(Connection $db, FileHandler $fileHandler)
+    {
+        parent::__construct($db);
+        $this->fileHandler = $fileHandler;
+    }
 }
diff --git a/src/Domain/Students/ApplicationFormFileGateway.php b/src/Domain/Students/ApplicationFormFileGateway.php
index 9117d850fc..48ea39f605 100644
--- a/src/Domain/Students/ApplicationFormFileGateway.php
+++ b/src/Domain/Students/ApplicationFormFileGateway.php
@@ -21,6 +21,8 @@
 
 namespace Gibbon\Domain\Students;
 
+use Gibbon\Contracts\Database\Connection;
+use Gibbon\Contracts\Filesystem\FileHandler;
 use Gibbon\Domain\QueryCriteria;
 use Gibbon\Domain\QueryableGateway;
 use Gibbon\Domain\ScrubbableGateway;
@@ -45,4 +47,15 @@ class ApplicationFormFileGateway extends QueryableGateway implements ScrubbableG
 
     private static $scrubbableKey = ['timestamp', 'gibbonApplicationForm', 'gibbonApplicationFormID'];
     private static $scrubbableColumns = ['path' => 'deleteFile'];
+
+    /**
+     * @var FileHandler
+     */
+    private $fileHandler;
+
+    public function __construct(Connection $db, FileHandler $fileHandler)
+    {
+        parent::__construct($db);
+        $this->fileHandler = $fileHandler;
+    }
 }
diff --git a/src/Domain/Students/MedicalConditionGateway.php b/src/Domain/Students/MedicalConditionGateway.php
index 4a06b3ccbf..bb6ddce79f 100644
--- a/src/Domain/Students/MedicalConditionGateway.php
+++ b/src/Domain/Students/MedicalConditionGateway.php
@@ -21,6 +21,8 @@
 
 namespace Gibbon\Domain\Students;
 
+use Gibbon\Contracts\Database\Connection;
+use Gibbon\Contracts\Filesystem\FileHandler;
 use Gibbon\Domain\QueryCriteria;
 use Gibbon\Domain\QueryableGateway;
 use Gibbon\Domain\ScrubbableGateway;
@@ -45,4 +47,15 @@ class MedicalConditionGateway extends QueryableGateway implements ScrubbableGate
 
     private static $scrubbableKey = ['gibbonPersonID', 'gibbonPersonMedical', 'gibbonPersonMedicalID'];
     private static $scrubbableColumns = ['name' => '','gibbonAlertLevelID'=> null,'triggers' => '','reaction' => '','response' => '','medication' => '','lastEpisode'=> null,'lastEpisodeTreatment' => '','comment' => '','attachment'=> 'deleteFile'];
+
+    /**
+     * @var FileHandler
+     */
+    private $fileHandler;
+
+    public function __construct(Connection $db, FileHandler $fileHandler)
+    {
+        parent::__construct($db);
+        $this->fileHandler = $fileHandler;
+    }
 }
diff --git a/src/Domain/Traits/Scrubbable.php b/src/Domain/Traits/Scrubbable.php
index 62fbe1529b..e27290d304 100644
--- a/src/Domain/Traits/Scrubbable.php
+++ b/src/Domain/Traits/Scrubbable.php
@@ -78,16 +78,26 @@ public function scrub(string $cutoffDate, array $context = []) : array
         }, $columns);
 
         // Handle files that need deleted along with the scrub
-        $absolutePath = $this->db()->selectOne("SELECT value FROM gibbonSetting WHERE scope='System' AND name='absolutePath'");
+        $absolutePath = null;
         foreach ($columns as $name => $property) {
             if ($property != 'deleteFile') continue;
 
             foreach ($scrubbable as $primaryKey => $values) {
-                $values = $this->getByID($primaryKey, [$name]);
                 $columns[$name] = 'Deleted File';
 
-                if (is_file($absolutePath.'/'.$values[$name])) {
-                    unlink($absolutePath.'/'.$values[$name]);
+                if (isset($this->fileHandler)) {
+                    // Use FileHandler to clean up gibbonFilePointer, gibbonFile, and the physical file
+                    $this->fileHandler->deleteFile($this->getTableName(), $primaryKey, $name);
+                } else {
+                    // Fallback: unlink the physical file directly
+                    if ($absolutePath === null) {
+                        $absolutePath = $this->db()->selectOne("SELECT value FROM gibbonSetting WHERE scope='System' AND name='absolutePath'");
+                    }
+                    $values = $this->getByID($primaryKey, [$name]);
+                    
+                    if (is_file($absolutePath.'/'.$values[$name])) {
+                        unlink($absolutePath.'/'.$values[$name]);
+                    }
                 }
             }
         }
diff --git a/src/Domain/User/PersonalDocumentGateway.php b/src/Domain/User/PersonalDocumentGateway.php
index 0266006662..03c9cffd04 100644
--- a/src/Domain/User/PersonalDocumentGateway.php
+++ b/src/Domain/User/PersonalDocumentGateway.php
@@ -21,13 +21,14 @@
 
 namespace Gibbon\Domain\User;
 
-use Gibbon\Services\Format;
-use Gibbon\Domain\QueryCriteria;
+use Gibbon\Contracts\Database\Connection;
+use Gibbon\Contracts\Filesystem\FileHandler;
 use Gibbon\Domain\QueryableGateway;
+use Gibbon\Domain\QueryCriteria;
 use Gibbon\Domain\ScrubbableGateway;
 use Gibbon\Domain\Traits\Scrubbable;
-use Gibbon\Domain\Traits\TableAware;
 use Gibbon\Domain\Traits\ScrubByTimestamp;
+use Gibbon\Domain\Traits\TableAware;
 
 /**
  * @version v22
@@ -47,6 +48,17 @@ class PersonalDocumentGateway extends QueryableGateway implements ScrubbableGate
     private static $scrubbableKey = 'timestamp';
     private static $scrubbableColumns = ['documentNumber' => null,'documentName' => null,'documentType' => null,'dateIssue' => null,'dateExpiry' => null,'filePath' => 'deleteFile','country' => null];
 
+    /**
+     * @var FileHandler
+     */
+    private $fileHandler;
+
+    public function __construct(Connection $db, FileHandler $fileHandler)
+    {
+        parent::__construct($db);
+        $this->fileHandler = $fileHandler;
+    }
+
     /**
      * @param QueryCriteria $criteria
      * @return DataSet
@@ -171,6 +183,15 @@ public function updatePersonalDocumentOwnership($foreignTableOld, $foreignTableO
 
     public function deletePersonalDocuments($foreignTable, $foreignTableID)
     {
+        // Clean up file pointers before deleting records
+        $data = ['foreignTable' => $foreignTable, 'foreignTableID' => $foreignTableID];
+        $sql = "SELECT gibbonPersonalDocumentID FROM gibbonPersonalDocument WHERE foreignTable=:foreignTable AND foreignTableID=:foreignTableID AND (filePath IS NOT NULL AND filePath != '')";
+        $documents = $this->db()->select($sql, $data)->fetchAll();
+
+        foreach ($documents as $document) {
+            $this->fileHandler->deleteFile('gibbonPersonalDocument', $document['gibbonPersonalDocumentID'], 'filePath');
+        }
+
         $data = ['foreignTable' => $foreignTable, 'foreignTableID' => $foreignTableID];
         $sql = "DELETE FROM gibbonPersonalDocument 
                 WHERE foreignTable=:foreignTable AND foreignTableID=:foreignTableID";
diff --git a/src/Filesystem/FileHandler.php b/src/Filesystem/FileHandler.php
index 620ca9e5ca..4e9270f1f9 100644
--- a/src/Filesystem/FileHandler.php
+++ b/src/Filesystem/FileHandler.php
@@ -197,7 +197,7 @@ public function deleteFile(string $foreignTable, int|string $foreignTableID, str
         $this->db->commit();
 
         // Delete physical file only after successful commit (if no other pointers existed)
-        if ($pointerCount == 0 &&!empty($absolutePath) && file_exists($absolutePath)) {
+        if ($pointerCount == 0 && !empty($absolutePath) && file_exists($absolutePath)) {
             unlink($absolutePath);
         }