From cba7e05d9873913d22d1d2f55dcf089a3ea54d14 Mon Sep 17 00:00:00 2001
From: Til Wegener <38760774+tilwegener@users.noreply.github.com>
Date: Thu, 14 Aug 2025 08:10:58 +0000
Subject: [PATCH] fix: handle attachment cleanup errors safely and surface
 messages

---
 .../controllers/archived-email.controller.ts  |  7 ++-
 .../src/services/ArchivedEmailService.ts      | 53 +++++++++++++------
 .../archived-emails/[id]/+page.svelte         |  8 ++-
 3 files changed, 48 insertions(+), 20 deletions(-)

diff --git a/packages/backend/src/api/controllers/archived-email.controller.ts b/packages/backend/src/api/controllers/archived-email.controller.ts
index 3faf007..3c2b704 100644
--- a/packages/backend/src/api/controllers/archived-email.controller.ts
+++ b/packages/backend/src/api/controllers/archived-email.controller.ts
@@ -47,8 +47,11 @@ export class ArchivedEmailController {
             return res.status(204).send();
         } catch (error) {
             console.error(`Delete archived email ${req.params.id} error:`, error);
-            if (error instanceof Error && error.message === 'Archived email not found') {
-                return res.status(404).json({ message: error.message });
+            if (error instanceof Error) {
+                if (error.message === 'Archived email not found') {
+                    return res.status(404).json({ message: error.message });
+                }
+                return res.status(500).json({ message: error.message });
             }
             return res.status(500).json({ message: 'An internal server error occurred' });
         }
diff --git a/packages/backend/src/services/ArchivedEmailService.ts b/packages/backend/src/services/ArchivedEmailService.ts
index 2c87afc..d374479 100644
--- a/packages/backend/src/services/ArchivedEmailService.ts
+++ b/packages/backend/src/services/ArchivedEmailService.ts
@@ -158,10 +158,9 @@ export class ArchivedEmailService {
 
         const storage = new StorageService();
 
-        // Load attachments before deleting the email
-        let emailAttachmentsResult: { attachmentId: string; storagePath: string }[] = [];
+        // Load and handle attachments before deleting the email itself
         if (email.hasAttachments) {
-            emailAttachmentsResult = await db
+            const emailAttachmentsResult = await db
                 .select({
                     attachmentId: attachments.id,
                     storagePath: attachments.storagePath,
@@ -169,24 +168,46 @@ export class ArchivedEmailService {
                 .from(emailAttachments)
                 .innerJoin(attachments, eq(emailAttachments.attachmentId, attachments.id))
                 .where(eq(emailAttachments.emailId, emailId));
+
+            try {
+                for (const attachment of emailAttachmentsResult) {
+                    const [refCount] = await db
+                        .select({ count: count(emailAttachments.emailId) })
+                        .from(emailAttachments)
+                        .where(eq(emailAttachments.attachmentId, attachment.attachmentId));
+
+                    if (refCount.count === 1) {
+                        await storage.delete(attachment.storagePath);
+                        await db
+                            .delete(emailAttachments)
+                            .where(
+                                and(
+                                    eq(emailAttachments.emailId, emailId),
+                                    eq(emailAttachments.attachmentId, attachment.attachmentId)
+                                )
+                            );
+                        await db
+                            .delete(attachments)
+                            .where(eq(attachments.id, attachment.attachmentId));
+                    } else {
+                        await db
+                            .delete(emailAttachments)
+                            .where(
+                                and(
+                                    eq(emailAttachments.emailId, emailId),
+                                    eq(emailAttachments.attachmentId, attachment.attachmentId)
+                                )
+                            );
+                    }
+                }
+            } catch {
+                throw new Error('Failed to delete email attachments');
+            }
         }
 
         // Delete the email file from storage
         await storage.delete(email.storagePath);
 
-        // Handle attachments: delete only if not referenced elsewhere
-        for (const attachment of emailAttachmentsResult) {
-            const [refCount] = await db
-                .select({ count: count(emailAttachments.emailId) })
-                .from(emailAttachments)
-                .where(eq(emailAttachments.attachmentId, attachment.attachmentId));
-
-            if (refCount.count === 1) {
-                await storage.delete(attachment.storagePath);
-                await db.delete(attachments).where(eq(attachments.id, attachment.attachmentId));
-            }
-        }
-
         const searchService = new SearchService();
         await searchService.deleteDocuments('emails', [emailId]);
 
diff --git a/packages/frontend/src/routes/dashboard/archived-emails/[id]/+page.svelte b/packages/frontend/src/routes/dashboard/archived-emails/[id]/+page.svelte
index e19c00d..0482bb9 100644
--- a/packages/frontend/src/routes/dashboard/archived-emails/[id]/+page.svelte
+++ b/packages/frontend/src/routes/dashboard/archived-emails/[id]/+page.svelte
@@ -48,9 +48,13 @@
                                 method: 'DELETE'
                         });
                         if (!response.ok) {
-                                throw new Error('Failed to delete email');
+                                const errorData = await response.json().catch(() => null);
+                                const message = errorData?.message || 'Failed to delete email';
+                                console.error('Delete failed:', message);
+                                alert(message);
+                                return;
                         }
-                        await goto('/dashboard/archived-emails');
+                        await goto('/dashboard/archived-emails', { invalidateAll: true });
                 } catch (error) {
                         console.error('Delete failed:', error);
                 } finally {