diff --git a/frontend/src/lib/pages/WelcomeAssistant.svelte b/frontend/src/lib/pages/WelcomeAssistant.svelte
index d183c8752..1fcd9f8e7 100644
--- a/frontend/src/lib/pages/WelcomeAssistant.svelte
+++ b/frontend/src/lib/pages/WelcomeAssistant.svelte
@@ -144,7 +144,9 @@
       window.location.reload();
     } catch (err) {
       console.error('Setup error:', err);
-      error = t('setup.setupError');
+      // Show the server's message when it sends one, for example a password over
+      // bcrypt's 72 byte input limit. The generic string stays as the fallback.
+      error = err?.message || t('setup.setupError');
       submitting = false;
     }
   }
diff --git a/internal/handlers/setup.go b/internal/handlers/setup.go
index 14e112bde..8c5e5ee7c 100644
--- a/internal/handlers/setup.go
+++ b/internal/handlers/setup.go
@@ -17,6 +17,10 @@ import (
 	"golang.org/x/crypto/bcrypt"
 )
 
+// bcrypt's input limit. x/crypto/bcrypt refuses inputs longer than this instead
+// of truncating them, so a password over 72 bytes cannot be hashed at all.
+const maxPasswordBytes = 72
+
 // AuthMiddleware interface to avoid circular imports
 type AuthMiddleware interface {
 	MarkSetupCompleted()
@@ -502,6 +506,13 @@ func (h *SetupHandler) validateSetupRequest(req models.SetupRequest) error {
 	if req.AdminUser.Password == "" {
 		return fmt.Errorf("admin password is required")
 	}
+	// bcrypt's input limit is 72 bytes, and x/crypto/bcrypt errors instead of
+	// truncating. An over-long password therefore surfaces as a 500 here and the
+	// UI shows a generic setup failure. Validate before hashing so the client gets
+	// an actionable message. len(string) counts bytes, which is what matters.
+	if len(req.AdminUser.Password) > maxPasswordBytes {
+		return fmt.Errorf("admin password must be %d bytes or fewer (bcrypt input limit)", maxPasswordBytes)
+	}
 
 	// Basic email validation
 	if !strings.Contains(req.AdminUser.Email, "@") {