diff --git a/cmake/Testing.cmake b/cmake/Testing.cmake
index 749512fb6..0d9988806 100644
--- a/cmake/Testing.cmake
+++ b/cmake/Testing.cmake
@@ -34,15 +34,16 @@ function(auto_test subsystem module extra_deps)
     COMMAND ${TEST_CROSSCOMPILING_EMULATOR} test_${module})
 endfunction()
 
-auto_test(core core ${${PROJECT_NAME}_RESOURCES})
+auto_test(core core "${${PROJECT_NAME}_RESOURCES}")
 auto_test(core contactid "")
 auto_test(core toxid "")
 auto_test(core toxstring "")
 auto_test(chatlog textformatter "")
-auto_test(net bsu ${${PROJECT_NAME}_RESOURCES}) # needs nodes list
+auto_test(net bsu "${${PROJECT_NAME}_RESOURCES}") # needs nodes list
 auto_test(persistence paths "")
 auto_test(persistence dbschema "")
 auto_test(persistence offlinemsgengine "")
+auto_test(persistence smileypack "${${PROJECT_NAME}_RESOURCES}") # needs emojione
 auto_test(model friendmessagedispatcher "")
 auto_test(model groupmessagedispatcher "")
 auto_test(model messageprocessor "")
diff --git a/test/persistence/smileypack_test.cpp b/test/persistence/smileypack_test.cpp
new file mode 100644
index 000000000..477737d8e
--- /dev/null
+++ b/test/persistence/smileypack_test.cpp
@@ -0,0 +1,117 @@
+/*
+    Copyright © 2021 by The qTox Project Contributors
+
+    This file is part of qTox, a Qt-based graphical interface for Tox.
+
+    qTox is libre software: you can redistribute it and/or modify
+    it under the terms of the GNU General Public License as published by
+    the Free Software Foundation, either version 3 of the License, or
+    (at your option) any later version.
+
+    qTox is distributed in the hope that it will be useful,
+    but WITHOUT ANY WARRANTY; without even the implied warranty of
+    MERCHANTABILITY or FITNESS FOR A PARTICULAR PURPOSE.  See the
+    GNU General Public License for more details.
+
+    You should have received a copy of the GNU General Public License
+    along with qTox.  If not, see <http://www.gnu.org/licenses/>.
+*/
+
+#include "src/persistence/smileypack.h"
+
+#include <QtTest/QtTest>
+#include <QSignalSpy>
+#include <QString>
+#include <QStandardPaths>
+
+#include <QGuiApplication>
+
+#include <memory>
+
+QString getAsRichText(const QString& key);
+
+class TestSmileyPack : public QObject
+{
+    Q_OBJECT
+public:
+    TestSmileyPack();
+
+private slots:
+    void testSmilifySingleCharEmoji();
+    void testSmilifyMultiCharEmoji();
+    void testSmilifyAsciiEmoticon();
+private:
+    std::unique_ptr<QGuiApplication> app;
+};
+
+TestSmileyPack::TestSmileyPack()
+{
+    static char arg1[]{"QToxSmileyPackTestApp"};
+    static char arg2[]{"-platform"};
+    static char arg3[]{"offscreen"};
+    static char* qtTestAppArgv[] = {arg1, arg2, arg3};
+    static int qtTestAppArgc = 3;
+
+    app = std::unique_ptr<QGuiApplication>(new QGuiApplication(qtTestAppArgc, qtTestAppArgv));
+}
+
+/**
+ * @brief Test that single-character emojis (non-ascii) are correctly smilified
+ */
+void TestSmileyPack::testSmilifySingleCharEmoji()
+{
+    auto& smileyPack = SmileyPack::getInstance();
+
+    auto result = smileyPack.smileyfied("😊");
+    QVERIFY(result == getAsRichText("😊"));
+
+    result = smileyPack.smileyfied("Some😊Letters");
+    QVERIFY(result == "Some" + getAsRichText("😊") + "Letters");
+}
+
+/**
+ * @brief Test that multi-character emojis (non-ascii) are correctly smilified
+ *  and not incorrectly matched against single-char counterparts
+ */
+void TestSmileyPack::testSmilifyMultiCharEmoji()
+{
+    auto& smileyPack = SmileyPack::getInstance();
+
+    auto result = smileyPack.smileyfied("🇬🇧");
+    QVERIFY(result == getAsRichText("🇬🇧"));
+
+    result = smileyPack.smileyfied("Some🇬🇧Letters");
+    QVERIFY(result == "Some" + getAsRichText("🇬🇧") + "Letters");
+
+    // This verifies that multi-char emojis are not accidentally
+    // considered a multichar ascii smiley
+    result = smileyPack.smileyfied("🇫🇷🇬🇧");
+    QVERIFY(result == getAsRichText("🇫🇷") + getAsRichText("🇬🇧"));
+}
+
+
+/**
+ * @brief Test that single character emojis (non-ascii) are correctly smilified
+ *  and not when surrounded by non-punctuation and non-whitespace chars
+ */
+void TestSmileyPack::testSmilifyAsciiEmoticon()
+{
+    auto& smileyPack = SmileyPack::getInstance();
+
+    auto result = smileyPack.smileyfied(":-)");
+    QVERIFY(result == getAsRichText(":-)"));
+
+    constexpr auto testMsg = "Some:-)Letters";
+    result = smileyPack.smileyfied(testMsg);
+
+    // Nothing has changed. Ascii smileys are only considered
+    // when they are surrounded by white space
+    QVERIFY(result == testMsg);
+
+    result = smileyPack.smileyfied("  :-)  ");
+    QVERIFY(result == "  " + getAsRichText(":-)") + "  ");
+}
+
+
+QTEST_GUILESS_MAIN(TestSmileyPack)
+#include "smileypack_test.moc"