diff --git a/artifacts/npm-outdated.json b/artifacts/npm-outdated.json
index d7613b9a..4b3da80f 100644
--- a/artifacts/npm-outdated.json
+++ b/artifacts/npm-outdated.json
@@ -13,6 +13,13 @@
     "dependent": "app",
     "location": "/app/node_modules/esbuild"
   },
+  "nostr-tools": {
+    "current": "2.20.0",
+    "wanted": "2.21.0",
+    "latest": "2.21.0",
+    "dependent": "app",
+    "location": "/app/node_modules/nostr-tools"
+  },
   "pixelmatch": {
     "current": "5.3.0",
     "wanted": "5.3.0",
diff --git a/issues/upgrade-nostr-tools.md b/issues/upgrade-nostr-tools.md
index 3a0c2ba6..6a743e67 100644
--- a/issues/upgrade-nostr-tools.md
+++ b/issues/upgrade-nostr-tools.md
@@ -1,8 +1,8 @@
 # Upgrade nostr-tools
 
-- **Current Version:** 2.19.4
-- **Wanted Version:** 2.20.0
-- **Latest Version:** 2.20.0
+- **Current Version:** 2.20.0
+- **Wanted Version:** 2.21.0
+- **Latest Version:** 2.21.0
 
 **Status:** Skipped (Risky/Protocol)
-**Reason:** This is a cryptographic/protocol library. As per security guardrails, manual review is required before upgrading.
+**Reason:** This is a cryptographic/protocol library. As per security guardrails, manual review is required before upgrading. The upgrade from 2.20 to 2.21 is minor but still falls under the "anything touching nostr-tools" policy.
diff --git a/tests/nostr-login-permissions.test.mjs b/tests/nostr-login-permissions.test.mjs
index 0fa80c4c..1a81e753 100644
--- a/tests/nostr-login-permissions.test.mjs
+++ b/tests/nostr-login-permissions.test.mjs
@@ -313,7 +313,7 @@ test("NIP-07 login falls back when structured permissions fail", async () => {
     const pubkey = result.pubkey;
     assert.equal(pubkey, HEX_PUBKEY);
     assert.ok(env.enableCalls.length >= 2, "should retry with alternate payloads");
-    const [objectCall, stringCall] = env.enableCalls;
+    const [objectCall, stringCall, plainCall] = env.enableCalls;
     assert.ok(Array.isArray(objectCall?.permissions));
     assert.equal(
       typeof objectCall.permissions[0],