diff --git a/packages/app-server/src/modules/notes/notes.repository.ts b/packages/app-server/src/modules/notes/notes.repository.ts
index 73196f11..79f0c473 100644
--- a/packages/app-server/src/modules/notes/notes.repository.ts
+++ b/packages/app-server/src/modules/notes/notes.repository.ts
@@ -1,8 +1,10 @@
 import type { Storage } from '../storage/storage.types';
 import type { DatabaseNote, Note } from './notes.types';
 import { injectArguments } from '@corentinth/chisels';
+import { isCustomError } from '../shared/errors/errors';
 import { generateId } from '../shared/utils/random';
-import { createNoteNotFoundError } from './notes.errors';
+import { KV_VALUE_LENGTH_EXCEEDED_ERROR_CODE } from '../storage/factories/cloudflare-kv.storage';
+import { createNoteNotFoundError, createNotePayloadTooLargeError } from './notes.errors';
 import { getNoteExpirationDate } from './notes.models';
 
 export { createNoteRepository };
@@ -52,38 +54,46 @@ async function saveNote(
     isPublic: boolean;
   },
 ): Promise<{ noteId: string }> {
-  const noteId = generateNoteId();
-  const baseNote = {
-    payload,
-    deleteAfterReading,
-    encryptionAlgorithm,
-    serializationFormat,
-    isPublic,
-  };
-
-  if (!ttlInSeconds) {
-    await storage.setItem(noteId, baseNote);
+  try {
+    const noteId = generateNoteId();
+    const baseNote = {
+      payload,
+      deleteAfterReading,
+      encryptionAlgorithm,
+      serializationFormat,
+      isPublic,
+    };
+
+    if (!ttlInSeconds) {
+      await storage.setItem(noteId, baseNote);
+
+      return { noteId };
+    }
+
+    const { expirationDate } = getNoteExpirationDate({ ttlInSeconds, now });
+
+    await storage.setItem(
+      noteId,
+      {
+        ...baseNote,
+        expirationDate: expirationDate.toISOString(),
+      },
+      {
+      // Some storage drivers have a different API for setting TTLs
+        ttl: ttlInSeconds,
+        // Cloudflare KV Binding - https://developers.cloudflare.com/kv/api/write-key-value-pairs/#create-expiring-keys
+        expirationTtl: ttlInSeconds,
+      },
+    );
 
     return { noteId };
-  }
+  } catch (error) {
+    if (isCustomError(error) && error.code === KV_VALUE_LENGTH_EXCEEDED_ERROR_CODE) {
+      throw createNotePayloadTooLargeError();
+    }
 
-  const { expirationDate } = getNoteExpirationDate({ ttlInSeconds, now });
-
-  await storage.setItem(
-    noteId,
-    {
-      ...baseNote,
-      expirationDate: expirationDate.toISOString(),
-    },
-    {
-      // Some storage drivers have a different API for setting TTLs
-      ttl: ttlInSeconds,
-      // Cloudflare KV Binding - https://developers.cloudflare.com/kv/api/write-key-value-pairs/#create-expiring-keys
-      expirationTtl: ttlInSeconds,
-    },
-  );
-
-  return { noteId };
+    throw error;
+  }
 }
 
 async function getNoteById({ noteId, storage }: { noteId: string; storage: Storage<DatabaseNote> }): Promise<{ note: Note }> {
diff --git a/packages/app-server/src/modules/storage/factories/cloudflare-kv.storage.models.test.ts b/packages/app-server/src/modules/storage/factories/cloudflare-kv.storage.models.test.ts
new file mode 100644
index 00000000..8625611d
--- /dev/null
+++ b/packages/app-server/src/modules/storage/factories/cloudflare-kv.storage.models.test.ts
@@ -0,0 +1,19 @@
+import { describe, expect, test } from 'vitest';
+import { looksLikeCloudflare413Error } from './cloudflare-kv.storage.models';
+
+describe('cloudflare-kv storage models', () => {
+  describe('looksLikeCloudflare413Error', () => {
+    test('a cloudflare 413 error starts with "KV PUT failed: 413 Value length of", everything else is not a cloudflare 413 error', () => {
+      expect(looksLikeCloudflare413Error({
+        error: new Error('KV PUT failed: 413 Value length of 41943339 exceeds limit of 26214400.'),
+      })).to.eql(true);
+
+      expect(looksLikeCloudflare413Error({
+        error: new Error('KV PUT failed: 429 Too many requests.'),
+      })).to.eql(false);
+
+      expect(looksLikeCloudflare413Error({ error: undefined })).to.eql(false);
+      expect(looksLikeCloudflare413Error({ error: 'foo' })).to.eql(false);
+    });
+  });
+});
diff --git a/packages/app-server/src/modules/storage/factories/cloudflare-kv.storage.models.ts b/packages/app-server/src/modules/storage/factories/cloudflare-kv.storage.models.ts
new file mode 100644
index 00000000..9a22486c
--- /dev/null
+++ b/packages/app-server/src/modules/storage/factories/cloudflare-kv.storage.models.ts
@@ -0,0 +1,11 @@
+import { isError } from 'lodash-es';
+
+export { looksLikeCloudflare413Error };
+
+function looksLikeCloudflare413Error({ error }: { error: unknown }) {
+  if (isError(error)) {
+    return error?.message?.startsWith('KV PUT failed: 413 Value length of') ?? false;
+  }
+
+  return false;
+}
diff --git a/packages/app-server/src/modules/storage/factories/cloudflare-kv.storage.ts b/packages/app-server/src/modules/storage/factories/cloudflare-kv.storage.ts
index abfe179f..519b5857 100644
--- a/packages/app-server/src/modules/storage/factories/cloudflare-kv.storage.ts
+++ b/packages/app-server/src/modules/storage/factories/cloudflare-kv.storage.ts
@@ -1,8 +1,12 @@
 import type { Driver } from 'unstorage';
+import { safely } from '@corentinth/chisels';
 import { createStorage } from 'unstorage';
 import cloudflareKVBindingDriver from 'unstorage/drivers/cloudflare-kv-binding';
 import { createError } from '../../shared/errors/errors';
 import { defineBindableStorageFactory } from '../storage.models';
+import { looksLikeCloudflare413Error } from './cloudflare-kv.storage.models';
+
+export const KV_VALUE_LENGTH_EXCEEDED_ERROR_CODE = 'storage.kv.value_length_exceeds_limit';
 
 export const createCloudflareKVStorageFactory = defineBindableStorageFactory(() => {
   return {
@@ -28,7 +32,22 @@ export const createCloudflareKVStorageFactory = defineBindableStorageFactory(()
         // Current : https://github.com/unjs/unstorage/blob/v1.10.2/src/drivers/cloudflare-kv-binding.ts
         // Future : https://github.com/unjs/unstorage/blob/main/src/drivers/cloudflare-kv-binding.ts
         async setItem(key, value, options) {
-          return binding.put(key, value, options);
+          const [result, error] = await safely(binding.put(key, value, options));
+
+          if (looksLikeCloudflare413Error({ error })) {
+            throw createError({
+              message: 'Value length exceeds limit',
+              code: KV_VALUE_LENGTH_EXCEEDED_ERROR_CODE,
+              statusCode: 413,
+              isInternal: true,
+            });
+          }
+
+          if (error) {
+            throw error;
+          }
+
+          return result;
         },
       };
 
diff --git a/packages/app-server/wrangler.toml b/packages/app-server/wrangler.toml
index dc0028da..482b967a 100644
--- a/packages/app-server/wrangler.toml
+++ b/packages/app-server/wrangler.toml
@@ -5,3 +5,8 @@ pages_build_output_dir = "./dist"
 [[kv_namespaces]]
 binding = "notes"
 id = "b1329cb8560e49d392bed877c9ac48a2"
+
+[vars]
+# Cloudfare KV value max size is 25Mib
+# https://developers.cloudflare.com/kv/platform/limits/
+NOTES_MAX_ENCRYPTED_PAYLOAD_LENGTH = 26214400