diff --git a/src/simplewallet/simplewallet.cpp b/src/simplewallet/simplewallet.cpp
index a78c233f8..ef604d9f3 100644
--- a/src/simplewallet/simplewallet.cpp
+++ b/src/simplewallet/simplewallet.cpp
@@ -6276,6 +6276,17 @@ void simple_wallet::check_for_inactivity_lock(bool user)
           break;
         }
       }
+      catch (const std::exception &e)
+      {
+        // Report why unlocking failed, rather than just looping back to the password prompt
+        auto writer = fail_msg_writer();
+        if (show_wallet_name)
+          writer << tr("Failed to unlock wallet: ") << e.what();
+        else
+          writer << tr("Failed to unlock wallet.");
+        if (m_wallet->key_on_device())
+          writer << "\n" << tr("Please ensure the HW wallet is connected and unlocked.");
+      }
       catch (...) { /* do nothing, just let the loop loop */ }
     }
     m_last_activity_time = time(NULL);