diff --git a/packages/api/src/resolvers/upload_files/index.ts b/packages/api/src/resolvers/upload_files/index.ts
index 58eca5370..93e622ea0 100644
--- a/packages/api/src/resolvers/upload_files/index.ts
+++ b/packages/api/src/resolvers/upload_files/index.ts
@@ -109,9 +109,12 @@ export const uploadFileRequestResolver = authorized<
       input.contentType
     )
 
+    // If this is a file URL, we swap in a special URL
+    const attachmentUrl = `https://omnivore.app/attachments/${uploadFilePathName}`
     if (isFileUrl(input.url)) {
       await authTrx(async (tx) => {
         await tx.getRepository(UploadFile).update(uploadFileId, {
+          url: attachmentUrl,
           status: UploadFileStatus.Initialized,
         })
       })
diff --git a/packages/api/src/routers/svc/email_attachment.ts b/packages/api/src/routers/svc/email_attachment.ts
index 096359673..6c127135b 100644
--- a/packages/api/src/routers/svc/email_attachment.ts
+++ b/packages/api/src/routers/svc/email_attachment.ts
@@ -142,7 +142,12 @@ export function emailAttachmentRouter() {
         return res.status(400).send('BAD REQUEST')
       }
 
-      const uploadFileUrlOverride = `https://omnivore.app/attachments/${uploadFileId}/${uploadFile.fileName}`
+      const uploadFilePathName = generateUploadFilePathName(
+        uploadFileId,
+        uploadFile.fileName
+      )
+
+      const uploadFileUrlOverride = `https://omnivore.app/attachments/${uploadFilePathName}`
       const uploadFileHash = uploadFileDetails.md5Hash
       const itemType =
         uploadFile.contentType === 'application/pdf'