diff --git a/kerfuffle/archive_kerfuffle.cpp b/kerfuffle/archive_kerfuffle.cpp
--- a/kerfuffle/archive_kerfuffle.cpp
+++ b/kerfuffle/archive_kerfuffle.cpp
@@ -306,9 +306,14 @@
         return Q_NULLPTR;
     }
 
-    qCDebug(ARK) << "Going to add files" << files << "with options" << options;
+    CompressionOptions newOptions = options;
+    if (encryptionType() != Unencrypted) {
+        newOptions[QStringLiteral("PasswordProtectedHint")] = true;
+    }
+
+    qCDebug(ARK) << "Going to add files" << files << "with options" << newOptions;
     Q_ASSERT(!m_iface->isReadOnly());
-    AddJob *newJob = new AddJob(files, options, static_cast<ReadWriteArchiveInterface*>(m_iface), this);
+    AddJob *newJob = new AddJob(files, newOptions, static_cast<ReadWriteArchiveInterface*>(m_iface), this);
     connect(newJob, &AddJob::result, this, &Archive::onAddFinished);
     return newJob;
 }
diff --git a/kerfuffle/cliinterface.cpp b/kerfuffle/cliinterface.cpp
--- a/kerfuffle/cliinterface.cpp
+++ b/kerfuffle/cliinterface.cpp
@@ -176,6 +176,17 @@
 
     m_operationMode = Add;
 
+    const QStringList addArgs = m_param.value(AddArgs).toStringList();
+
+    if (addArgs.contains(QStringLiteral("$PasswordSwitch")) &&
+        options.value(QStringLiteral("PasswordProtectedHint")).toBool() &&
+        password().isEmpty()) {
+        qCDebug(ARK) << "Password hint enabled, querying user";
+        if (!passwordQuery()) {
+            return false;
+        }
+    }
+
     int compLevel = options.value(QStringLiteral("CompressionLevel"), -1).toInt();
 
     const auto args = substituteAddVariables(m_param.value(AddArgs).toStringList(),
diff --git a/kerfuffle/queries.cpp b/kerfuffle/queries.cpp
--- a/kerfuffle/queries.cpp
+++ b/kerfuffle/queries.cpp
@@ -176,7 +176,7 @@
     QApplication::setOverrideCursor(QCursor(Qt::ArrowCursor));
 
     QPointer<KPasswordDialog> dlg = new KPasswordDialog;
-    dlg.data()->setPrompt(xi18nc("@info", "The archive <filename>%1</filename> is password protected. Please enter the password to extract the file.",
+    dlg.data()->setPrompt(xi18nc("@info", "The archive <filename>%1</filename> is password protected. Please enter the password.",
                                  m_data.value(QStringLiteral("archiveFilename")).toString()));
 
     if (m_data.value(QStringLiteral("incorrectTryAgain")).toBool()) {