diff --git a/src/encryptid/server.ts b/src/encryptid/server.ts
index 69b75915..20c65538 100644
--- a/src/encryptid/server.ts
+++ b/src/encryptid/server.ts
@@ -579,8 +579,17 @@ app.post('/api/register/start', async (c) => {
   // Generate challenge
   const challenge = Buffer.from(crypto.getRandomValues(new Uint8Array(32))).toString('base64url');
 
-  // Generate user ID
-  const userId = Buffer.from(crypto.getRandomValues(new Uint8Array(32))).toString('base64url');
+  // Derive userId deterministically from username so repeated /start calls for
+  // the same username produce the same WebAuthn user.id. Per WebAuthn spec, a
+  // repeated create() ceremony with the same (rpId, user.id) overwrites the
+  // existing passkey instead of creating a new one — stops failed retries from
+  // leaving orphan passkeys behind in the user's password manager.
+  const userIdSalt = process.env.USER_ID_SALT || process.env.JWT_SECRET || 'encryptid-user-id';
+  const userIdBuf = await crypto.subtle.digest(
+    'SHA-256',
+    new TextEncoder().encode(`${userIdSalt}:${username.toLowerCase()}`),
+  );
+  const userId = Buffer.from(userIdBuf).toString('base64url');
 
   // Store challenge in database
   const challengeRecord: StoredChallenge = {