diff --git a/pkg/models/listeners.go b/pkg/models/listeners.go
index 6112b8f3a..7317ce949 100644
--- a/pkg/models/listeners.go
+++ b/pkg/models/listeners.go
@@ -896,65 +896,152 @@ func getProjectIDFromAnyEvent(eventPayload map[string]interface{}) int64 {
 	return 0
 }
 
+func reloadDoerInEvent(s *xorm.Session, event map[string]interface{}) (doerID int64, err error) {
+	doer, has := event["doer"]
+	if !has || doer == nil {
+		return 0, nil
+	}
+
+	// doer can be null in incoming payloads, so guard the type assertion
+	d, ok := doer.(map[string]interface{})
+	if !ok {
+		return 0, nil
+	}
+
+	rawDoerID, has := d["id"]
+	if !has || rawDoerID == nil {
+		return 0, nil
+	}
+
+	doerID = getIDAsInt64(rawDoerID)
+	if doerID <= 0 {
+		return 0, nil
+	}
+
+	fullDoer, err := user.GetUserByID(s, doerID)
+	if err != nil && !user.IsErrUserDoesNotExist(err) {
+		return 0, err
+	}
+	if err == nil {
+		event["doer"] = fullDoer
+	}
+
+	return doerID, nil
+}
+
+func reloadTaskInEvent(s *xorm.Session, event map[string]interface{}, doerID int64) error {
+	task, has := event["task"]
+	if !has || task == nil || doerID == 0 {
+		return nil
+	}
+
+	// guard the type assertion for task as well
+	t, ok := task.(map[string]interface{})
+	if !ok {
+		return nil
+	}
+
+	taskID, has := t["id"]
+	if !has || taskID == nil {
+		return nil
+	}
+
+	id := getIDAsInt64(taskID)
+	if id <= 0 {
+		return nil
+	}
+
+	fullTask := Task{
+		ID: id,
+		Expand: []TaskCollectionExpandable{
+			TaskCollectionExpandBuckets,
+		},
+	}
+	err := fullTask.ReadOne(s, &user.User{ID: doerID})
+	if err != nil && !IsErrTaskDoesNotExist(err) {
+		return err
+	}
+	if err == nil {
+		event["task"] = fullTask
+	}
+
+	return nil
+}
+
+func reloadProjectInEvent(s *xorm.Session, event map[string]interface{}, projectID, doerID int64) error {
+	_, has := event["project"]
+	if !has || doerID == 0 {
+		return nil
+	}
+
+	project, err := GetProjectSimpleByID(s, projectID)
+	if err != nil {
+		if IsErrProjectDoesNotExist(err) {
+			return nil
+		}
+		return err
+	}
+
+	err = project.ReadOne(s, &user.User{ID: doerID})
+	if err != nil && !IsErrProjectDoesNotExist(err) {
+		return err
+	}
+
+	if err == nil {
+		event["project"] = project
+	}
+
+	return nil
+}
+
+func reloadAssigneeInEvent(s *xorm.Session, event map[string]interface{}) error {
+	assignee, has := event["assignee"]
+	if !has || assignee == nil {
+		return nil
+	}
+
+	a, ok := assignee.(map[string]interface{})
+	if !ok {
+		return nil
+	}
+
+	assigneeID := getIDAsInt64(a["id"])
+	if assigneeID <= 0 {
+		return nil
+	}
+
+	fullAssignee, err := user.GetUserByID(s, assigneeID)
+	if err != nil && !user.IsErrUserDoesNotExist(err) {
+		return err
+	}
+	if err == nil {
+		event["assignee"] = fullAssignee
+	}
+
+	return nil
+}
+
 func reloadEventData(s *xorm.Session, event map[string]interface{}, projectID int64) (eventWithData map[string]interface{}, doerID int64, err error) {
 	// Load event data again so that it is always populated in the webhook payload
-	if doer, has := event["doer"]; has && doer != nil {
-		// doer can be null in incoming payloads, so guard the type assertion
-		d, ok := doer.(map[string]interface{})
-		if ok {
-			if rawDoerID, has := d["id"]; has && rawDoerID != nil {
-				doerID = getIDAsInt64(rawDoerID)
-				if doerID > 0 {
-					fullDoer, err := user.GetUserByID(s, doerID)
-					if err != nil && !user.IsErrUserDoesNotExist(err) {
-						return nil, 0, err
-					}
-					if err == nil {
-						event["doer"] = fullDoer
-					}
-				}
-			}
-		}
+
+	doerID, err = reloadDoerInEvent(s, event)
+	if err != nil {
+		return nil, 0, err
 	}
 
-	if task, has := event["task"]; has && task != nil && doerID != 0 {
-		// guard the type assertion for task as well
-		t, ok := task.(map[string]interface{})
-		if ok {
-			if taskID, has := t["id"]; has && taskID != nil {
-				id := getIDAsInt64(taskID)
-				if id > 0 {
-					fullTask := Task{
-						ID: id,
-						Expand: []TaskCollectionExpandable{
-							TaskCollectionExpandBuckets,
-						},
-					}
-					err = fullTask.ReadOne(s, &user.User{ID: doerID})
-					if err != nil && !IsErrTaskDoesNotExist(err) {
-						return
-					}
-					if err == nil {
-						event["task"] = fullTask
-					}
-				}
-			}
-		}
+	err = reloadTaskInEvent(s, event, doerID)
+	if err != nil {
+		return nil, doerID, err
 	}
 
-	if _, has := event["project"]; has && doerID != 0 {
-		var project *Project
-		project, err = GetProjectSimpleByID(s, projectID)
-		if err != nil && !IsErrProjectDoesNotExist(err) {
-			return
-		}
-		err = project.ReadOne(s, &user.User{ID: doerID})
-		if err != nil && !IsErrProjectDoesNotExist(err) {
-			return
-		}
-		if err == nil {
-			event["project"] = project
-		}
+	err = reloadProjectInEvent(s, event, projectID, doerID)
+	if err != nil {
+		return nil, doerID, err
+	}
+
+	err = reloadAssigneeInEvent(s, event)
+	if err != nil {
+		return nil, doerID, err
 	}
 
 	return event, doerID, nil
diff --git a/pkg/models/task_attachment.go b/pkg/models/task_attachment.go
index 9dcb1b806..10d9b1ffb 100644
--- a/pkg/models/task_attachment.go
+++ b/pkg/models/task_attachment.go
@@ -121,7 +121,17 @@ func (ta *TaskAttachment) ReadOne(s *xorm.Session, _ web.Auth) (err error) {
 	// Get the file
 	ta.File = &files.File{ID: ta.FileID}
 	err = ta.File.LoadFileMetaByID()
-	return
+	if err != nil {
+		return
+	}
+
+	// Get the creator (non-fatal if user doesn't exist)
+	ta.CreatedBy, err = user.GetUserByID(s, ta.CreatedByID)
+	if err != nil && !user.IsErrUserDoesNotExist(err) {
+		return err
+	}
+
+	return nil
 }
 
 // ReadAll returns a project with all attachments
diff --git a/pkg/models/task_comments.go b/pkg/models/task_comments.go
index ae827ef6c..17decfc44 100644
--- a/pkg/models/task_comments.go
+++ b/pkg/models/task_comments.go
@@ -118,7 +118,12 @@ func (tc *TaskComment) CreateWithTimestamps(s *xorm.Session, a web.Auth) (err er
 // @Failure 404 {object} web.HTTPError "The task comment was not found."
 // @Failure 500 {object} models.Message "Internal error"
 // @Router /tasks/{taskID}/comments/{commentID} [delete]
-func (tc *TaskComment) Delete(s *xorm.Session, _ web.Auth) error {
+func (tc *TaskComment) Delete(s *xorm.Session, a web.Auth) error {
+	err := tc.ReadOne(s, a)
+	if err != nil {
+		return err
+	}
+
 	deleted, err := s.
 		ID(tc.ID).
 		NoAutoCondition().
@@ -131,6 +136,7 @@ func (tc *TaskComment) Delete(s *xorm.Session, _ web.Auth) error {
 		return err
 	}
 
+	doer, _ := user.GetFromAuth(a)
 	task, err := GetTaskByIDSimple(s, tc.TaskID)
 	if err != nil {
 		return err
@@ -139,7 +145,7 @@ func (tc *TaskComment) Delete(s *xorm.Session, _ web.Auth) error {
 	return events.Dispatch(&TaskCommentDeletedEvent{
 		Task:    &task,
 		Comment: tc,
-		Doer:    tc.Author,
+		Doer:    doer,
 	})
 }
 
diff --git a/pkg/models/task_relation.go b/pkg/models/task_relation.go
index bb75f6148..3b55b38f4 100644
--- a/pkg/models/task_relation.go
+++ b/pkg/models/task_relation.go
@@ -20,12 +20,11 @@ import (
 	"time"
 
 	"code.vikunja.io/api/pkg/events"
+	"code.vikunja.io/api/pkg/user"
+	"code.vikunja.io/api/pkg/web"
 
 	"xorm.io/builder"
 	"xorm.io/xorm"
-
-	"code.vikunja.io/api/pkg/user"
-	"code.vikunja.io/api/pkg/web"
 )
 
 // RelationKind represents a kind of relation between to tasks
@@ -270,6 +269,31 @@ func (rel *TaskRelation) Create(s *xorm.Session, a web.Auth) error {
 	})
 }
 
+// ReadOne returns a task relation
+func (rel *TaskRelation) ReadOne(s *xorm.Session, _ web.Auth) (err error) {
+	exists, err := s.
+		Where("task_id = ? AND other_task_id = ? AND relation_kind = ?", rel.TaskID, rel.OtherTaskID, rel.RelationKind).
+		Get(rel)
+	if err != nil {
+		return err
+	}
+	if !exists {
+		return ErrRelationDoesNotExist{
+			TaskID:      rel.TaskID,
+			OtherTaskID: rel.OtherTaskID,
+			Kind:        rel.RelationKind,
+		}
+	}
+
+	// Get the creator
+	rel.CreatedBy, err = user.GetUserByID(s, rel.CreatedByID)
+	if err != nil && !user.IsErrUserDoesNotExist(err) {
+		return err
+	}
+
+	return nil
+}
+
 // Delete removes a task relation
 // @Summary Remove a task relation
 // @tags task
@@ -286,7 +310,13 @@ func (rel *TaskRelation) Create(s *xorm.Session, a web.Auth) error {
 // @Failure 500 {object} models.Message "Internal error"
 // @Router /tasks/{taskID}/relations/{relationKind}/{otherTaskID} [delete]
 func (rel *TaskRelation) Delete(s *xorm.Session, a web.Auth) error {
+	// Load the full relation first (populates CreatedBy)
+	err := rel.ReadOne(s, a)
+	if err != nil {
+		return err
+	}
 
+	// Build condition for deleting both the forward and inverse relations
 	cond := builder.Or(
 		builder.And(
 			builder.Eq{"task_id": rel.TaskID},
@@ -300,21 +330,6 @@ func (rel *TaskRelation) Delete(s *xorm.Session, a web.Auth) error {
 		),
 	)
 
-	// Check if the relation exists
-	exists, err := s.
-		Where(cond).
-		Exist(&TaskRelation{})
-	if err != nil {
-		return err
-	}
-	if !exists {
-		return ErrRelationDoesNotExist{
-			TaskID:      rel.TaskID,
-			OtherTaskID: rel.OtherTaskID,
-			Kind:        rel.RelationKind,
-		}
-	}
-
 	_, err = s.
 		Where(cond).
 		Delete(&TaskRelation{})