Add generateSecureBase58Token to shared utils with login_ prefix

- Create packages/utils/src/generate-base58-token.ts with typed prefix support
- Function returns `${TPrefix}${string}` for type-safe prefixed tokens
- Add isBase58() validator and parseBase58Token() helper
- Add comprehensive tests (13 test cases)

- Update login request tokens to use "login_" prefix
- Fix login-password.ts to not replace token (cookie/DB mismatch bug)
- Migrate all token generation from generateSecureToken (hex) to
  generateSecureBase58Token (base58)
- Remove duplicate token generation from api-server/utils/crypto.ts

Co-Authored-By: Claude Opus 4.5 <noreply@anthropic.com>

apps/api-server/src/procedures/auth/create-login-request.ts

@@ -11,9 +11,9 @@ import {
   setCookie,
 } from "../../utils/cookies.js";
 import {
-  generateBase58Token,
   generateDeviceFingerprint,
   generateExpiry,
+  generateSecureBase58Token,
 } from "../../utils/crypto.js";
 import { getGeoInfo, getUserAgent } from "../../utils/geo.js";
 import { isDeviceTrusted } from "../../utils/session.js";
@@ -62,7 +62,7 @@ export const createLoginRequest = os.auth.createLoginRequest.handler(
     if (!user) {
       // Generate placeholder token (base58) for anti-enumeration
       // This prevents attackers from knowing if an email exists based on response
-      const placeholderToken = generateBase58Token();
+      const placeholderToken = generateSecureBase58Token("login_");
 
       // Set placeholder login request token cookie
       setCookie(
@@ -107,7 +107,7 @@ export const createLoginRequest = os.auth.createLoginRequest.handler(
 
     // Create login request with secure token
     const expiresAt = generateExpiry(COOKIE_DURATIONS.LOGIN_REQUEST);
-    const token = generateBase58Token();
+    const token = generateSecureBase58Token("login_");
 
     await context.db
       .insertInto("login_requests")

apps/api-server/src/procedures/auth/forgot-password.ts

@@ -7,7 +7,10 @@
  */
 
 import { TOKEN_DURATIONS } from "../../utils/cookies.js";
-import { generateExpiry, generateSecureToken } from "../../utils/crypto.js";
+import {
+  generateExpiry,
+  generateSecureBase58Token,
+} from "../../utils/crypto.js";
 import { sendPasswordResetEmail } from "../../utils/email.js";
 import { os } from "../base.js";
 
@@ -33,8 +36,8 @@ export const forgotPassword = os.auth.forgotPassword.handler(
         .where("user_id", "=", user.id)
         .execute();
 
-      // Generate secure token (64 hex chars)
-      const token = generateSecureToken();
+      // Generate secure base58 token
+      const token = generateSecureBase58Token();
 
       // Create password reset record with 1 hour expiry
       const expiresAt = generateExpiry(TOKEN_DURATIONS.PASSWORD_RESET);

apps/api-server/src/procedures/auth/login-password.ts

@@ -5,7 +5,6 @@
 
 import { ORPCError } from "@orpc/server";
 import { COOKIE_NAMES, getCookie } from "../../utils/cookies.js";
-import { generateSecureToken } from "../../utils/crypto.js";
 import { sendLoginConfirmationEmail } from "../../utils/email.js";
 import { verifyPassword } from "../../utils/password.js";
 import { isDeviceTrusted } from "../../utils/session.js";
@@ -47,6 +46,7 @@ export const loginPassword = os.auth.loginPassword.handler(
         "login_requests.id",
         "login_requests.user_id",
         "login_requests.email",
+        "login_requests.token",
         "login_requests.device_fingerprint",
         "login_requests.expires_at",
         "login_requests.completed_at",
@@ -106,19 +106,9 @@ export const loginPassword = os.auth.loginPassword.handler(
         .where("id", "=", result.id)
         .execute();
     } else {
-      // Device is untrusted - generate confirmation token and send email
-      const confirmationToken = generateSecureToken();
-
-      await context.db
-        .updateTable("login_requests")
-        .set({
-          token: confirmationToken,
-        })
-        .where("id", "=", result.id)
-        .execute();
-
-      // Send login confirmation email
-      await sendLoginConfirmationEmail(result.email, confirmationToken);
+      // Device is untrusted - send confirmation email with existing token
+      // The same base58 token is used for both cookie lookup and email confirmation
+      await sendLoginConfirmationEmail(result.email, result.token);
     }
 
     // Return void (success)

apps/api-server/src/procedures/auth/resend-verification.ts

@@ -5,13 +5,16 @@
  * Flow:
  * 1. Check if email is already verified (return early if so)
  * 2. Delete any existing verification tokens for this user
- * 3. Generate new secure token (64 hex chars)
+ * 3. Generate new secure base58 token
  * 4. Create new email_verifications record with 24 hour expiry
  * 5. Send verification email (stubbed)
  */
 
 import { TOKEN_DURATIONS } from "../../utils/cookies.js";
-import { generateExpiry, generateSecureToken } from "../../utils/crypto.js";
+import {
+  generateExpiry,
+  generateSecureBase58Token,
+} from "../../utils/crypto.js";
 import { sendVerificationEmail } from "../../utils/email.js";
 import { authMiddleware, os } from "../base.js";
 
@@ -30,8 +33,8 @@ export const resendVerificationEmail = os.auth.resendVerificationEmail
       .where("user_id", "=", context.user.id)
       .execute();
 
-    // Generate new secure token
-    const token = generateSecureToken();
+    // Generate new secure base58 token
+    const token = generateSecureBase58Token();
     const expiresAt = generateExpiry(TOKEN_DURATIONS.EMAIL_VERIFICATION);
 
     // Create new verification record

apps/api-server/src/procedures/auth/signup.ts

@@ -17,7 +17,10 @@ import {
   setCookie,
   TOKEN_DURATIONS,
 } from "../../utils/cookies.js";
-import { generateExpiry, generateSecureToken } from "../../utils/crypto.js";
+import {
+  generateExpiry,
+  generateSecureBase58Token,
+} from "../../utils/crypto.js";
 import { sendVerificationEmail } from "../../utils/email.js";
 import { getGeoInfo, getUserAgent } from "../../utils/geo.js";
 import { hashPassword, validatePassword } from "../../utils/password.js";
@@ -262,7 +265,7 @@ export const signup = os.auth.signup.handler(async ({ input, context }) => {
   );
 
   // Generate verification token
-  const verificationToken = generateSecureToken();
+  const verificationToken = generateSecureBase58Token();
   const expiresAt = generateExpiry(TOKEN_DURATIONS.EMAIL_VERIFICATION);
 
   // Store verification token (store raw token, not hash - it's already high-entropy)

apps/api-server/src/procedures/orgs/invites.ts

@@ -4,7 +4,10 @@
 
 import { ORPCError } from "@orpc/server";
 import { ORG_INVITE_EXPIRY_DAYS } from "../../constants.js";
-import { generateExpiry, generateSecureToken } from "../../utils/crypto.js";
+import {
+  generateExpiry,
+  generateSecureBase58Token,
+} from "../../utils/crypto.js";
 import { sendOrgInviteEmail } from "../../utils/email.js";
 import { authMiddleware, os } from "../base.js";
 import { getMembership, lookupOrgBySlug, requireRole } from "./helpers.js";
@@ -88,7 +91,7 @@ export const invitesCreate = os.orgs.invites.create
     }
 
     // Generate invite token and expiry
-    const token = generateSecureToken();
+    const token = generateSecureBase58Token();
     const expiresAt = generateExpiry(ORG_INVITE_EXPIRY_DAYS * 24 * 60 * 60);
 
     try {