diff --git a/apps/web/src/common/attachments.ts b/apps/web/src/common/attachments.ts
index 442662d8b..1adb56ef5 100644
--- a/apps/web/src/common/attachments.ts
+++ b/apps/web/src/common/attachments.ts
@@ -106,9 +106,12 @@ export async function checkAttachment(hash: string) {
       import("../interfaces/fs"),
       ({ getUploadedFileSize }) => getUploadedFileSize(hash)
     );
-    if (size <= 0) return { failed: "File length is 0." };
+    if (size === 0) throw new Error("File length is 0.");
+    else if (size === -1) throw new Error("File verification check failed.");
   } catch (e) {
-    return { failed: e instanceof Error ? e.message : "Unknown error." };
+    const reason = e instanceof Error ? e.message : "Unknown error.";
+    await db.attachments.markAsFailed(attachment.id, reason);
+    return { failed: reason };
   }
   return { success: true };
 }
diff --git a/apps/web/src/components/editor/picker.ts b/apps/web/src/components/editor/picker.ts
index 5ee058c95..51bfd2ddc 100644
--- a/apps/web/src/components/editor/picker.ts
+++ b/apps/web/src/components/editor/picker.ts
@@ -189,7 +189,7 @@ async function addAttachment(
 
     const exists = await db.attachments.attachment(hash);
     if (!forceWrite && exists) {
-      forceWrite = (await getUploadedFileSize(hash)) <= 0;
+      forceWrite = (await getUploadedFileSize(hash)) === 0;
     }
 
     if (forceWrite || !exists) {
diff --git a/apps/web/src/interfaces/fs.ts b/apps/web/src/interfaces/fs.ts
index 3e6629ab1..2d595781e 100644
--- a/apps/web/src/interfaces/fs.ts
+++ b/apps/web/src/interfaces/fs.ts
@@ -49,6 +49,7 @@ import {
   Output,
   RequestOptions
 } from "@notesnook/core/dist/interfaces";
+import { logger } from "../utils/logger";
 
 const ABYTES = 17;
 const CHUNK_SIZE = 512 * 1024;
@@ -624,6 +625,13 @@ async function deleteFile(
   }
 }
 
+/**
+ * `-1` means an error during file size
+ *
+ * `0` means file either doesn't exist or file is actually of 0 length
+ *
+ * `>0` means file is valid
+ */
 export async function getUploadedFileSize(filename: string) {
   try {
     const url = `${hosts.API_HOST}/s3?name=${filename}`;
@@ -636,8 +644,8 @@ export async function getUploadedFileSize(filename: string) {
     const contentLength = parseInt(attachmentInfo.headers["content-length"]);
     return isNaN(contentLength) ? 0 : contentLength;
   } catch (e) {
-    console.error(e);
-    return 0;
+    logger.error(e, "Failed to get uploaded file size.", { filename });
+    return -1;
   }
 }