diff --git a/build_msvc/test_bitcoin-qt/test_bitcoin-qt.vcxproj b/build_msvc/test_bitcoin-qt/test_bitcoin-qt.vcxproj
index 16514a0a7c1..a0feeb86f34 100644
--- a/build_msvc/test_bitcoin-qt/test_bitcoin-qt.vcxproj
+++ b/build_msvc/test_bitcoin-qt/test_bitcoin-qt.vcxproj
@@ -14,6 +14,7 @@
     <ClCompile Include="..\..\src\qt\test\addressbooktests.cpp" />
     <ClCompile Include="..\..\src\qt\test\apptests.cpp" />
     <ClCompile Include="..\..\src\qt\test\importdescriptorstests.cpp" />
+    <ClCompile Include="..\..\src\qt\test\importlegacytests.cpp" />
     <ClCompile Include="..\..\src\qt\test\importmultitests.cpp" />
     <ClCompile Include="..\..\src\qt\test\optiontests.cpp" />
     <ClCompile Include="..\..\src\qt\test\rpcnestedtests.cpp" />
@@ -25,6 +26,7 @@
     <ClCompile Include="$(GeneratedFilesOutDir)\moc\moc_addressbooktests.cpp" />
     <ClCompile Include="$(GeneratedFilesOutDir)\moc\moc_apptests.cpp" />
     <ClCompile Include="$(GeneratedFilesOutDir)\moc\moc_importdescriptorstests.cpp" />
+    <ClCompile Include="$(GeneratedFilesOutDir)\moc\moc_importlegacytests.cpp" />
     <ClCompile Include="$(GeneratedFilesOutDir)\moc\moc_importmultitests.cpp" />
     <ClCompile Include="$(GeneratedFilesOutDir)\moc\moc_optiontests.cpp" />
     <ClCompile Include="$(GeneratedFilesOutDir)\moc\moc_rpcnestedtests.cpp" />
@@ -99,6 +101,7 @@
     <MocTestFiles Include="..\..\src\qt\test\addressbooktests.h" />
     <MocTestFiles Include="..\..\src\qt\test\apptests.h" />
     <MocTestFiles Include="..\..\src\qt\test\importdescriptorstests.h" />
+    <MocTestFiles Include="..\..\src\qt\test\importlegacytests.h" />
     <MocTestFiles Include="..\..\src\qt\test\importmultitests.h" />
     <MocTestFiles Include="..\..\src\qt\test\optiontests.h" />
     <MocTestFiles Include="..\..\src\qt\test\rpcnestedtests.h" />
diff --git a/src/Makefile.qttest.include b/src/Makefile.qttest.include
index 088ef310183..743c8ea2824 100644
--- a/src/Makefile.qttest.include
+++ b/src/Makefile.qttest.include
@@ -15,6 +15,7 @@ if ENABLE_WALLET
 TEST_QT_MOC_CPP += \
   qt/test/moc_addressbooktests.cpp \
   qt/test/moc_importdescriptorstests.cpp \
+  qt/test/moc_importlegacytests.cpp \
   qt/test/moc_importmultitests.cpp \
   qt/test/moc_wallettests.cpp
 endif # ENABLE_WALLET
@@ -23,6 +24,7 @@ TEST_QT_H = \
   qt/test/addressbooktests.h \
   qt/test/apptests.h \
   qt/test/importdescriptorstests.h \
+  qt/test/importlegacytests.h \
   qt/test/importmultitests.h \
   qt/test/optiontests.h \
   qt/test/rpcnestedtests.h \
@@ -45,6 +47,7 @@ if ENABLE_WALLET
 qt_test_test_bitcoin_qt_SOURCES += \
   qt/test/addressbooktests.cpp \
   qt/test/importdescriptorstests.cpp \
+  qt/test/importlegacytests.cpp \
   qt/test/importmultitests.cpp \
   qt/test/wallettests.cpp \
   qt/test/util.cpp \
diff --git a/src/qt/test/importlegacytests.cpp b/src/qt/test/importlegacytests.cpp
new file mode 100644
index 00000000000..a20fb004f50
--- /dev/null
+++ b/src/qt/test/importlegacytests.cpp
@@ -0,0 +1,223 @@
+// Copyright (c) 2023 The Bitcoin Core developers
+// Distributed under the MIT software license, see the accompanying
+// file COPYING or http://www.opensource.org/licenses/mit-license.php.
+
+#include <qt/test/importlegacytests.h>
+#include <qt/test/util.h>
+#include <test/util/setup_common.h>
+
+#include <interfaces/chain.h>
+#include <interfaces/node.h>
+#include <qt/bitcoinamountfield.h>
+#include <qt/importdialog.h>
+#include <qt/clientmodel.h>
+#include <qt/editaddressdialog.h>
+#include <qt/optionsmodel.h>
+#include <qt/platformstyle.h>
+#include <qt/qvalidatedlineedit.h>
+#include <qt/walletmodel.h>
+
+#include <key_io.h>
+#include <script/standard.h>
+#include <validation.h>
+#include <wallet/coincontrol.h>
+#include <wallet/spend.h>
+#include <wallet/wallet.h>
+#include <wallet/test/util.h>
+#include <walletinitinterface.h>
+
+#include <chrono>
+
+#include <QApplication>
+#include <QCheckBox>
+#include <QLineEdit>
+#include <QString>
+
+using wallet::AddWallet;
+using wallet::CreateMockWalletDatabase;
+using wallet::CWallet;
+using wallet::RemoveWallet;
+using wallet::WalletContext;
+
+struct ImportKeyData
+{
+    QString key;
+    QString label;
+    bool rescan = true;
+    bool p2sh = false;
+};
+
+void EditKeyAndSubmit(ImportDialog* dialog, ImportDialog::Page _page, const ImportKeyData& data, QString expected_msg) {
+    QString warning_text;
+
+    dialog->findChild<QLineEdit*>("keyEditIKP")->setText(data.key);
+    dialog->findChild<QLineEdit*>("labelEditIKP")->setText(data.label);
+    dialog->findChild<QCheckBox*>("rescanButtonIKP")->setChecked(data.rescan);
+    if (_page == ImportDialog::importAddress) {
+        dialog->findChild<QCheckBox*>("p2shButtonIKP")->setChecked(data.p2sh);
+    }
+
+    ConfirmMessage(&warning_text, 5ms);
+    dialog->accept();
+    QCOMPARE(warning_text, expected_msg);
+}
+
+void TestImportLegacy(interfaces::Node& node)
+{
+    // Set up wallet and chain with 105 blocks.
+    TestChain100Setup test;
+    auto wallet_loader = interfaces::MakeWalletLoader(*test.m_node.chain, *Assert(test.m_node.args));
+    test.m_node.wallet_loader = wallet_loader.get();
+    node.setContext(&test.m_node);
+    const std::shared_ptr<CWallet> wallet = std::make_shared<CWallet>(node.context()->chain.get(), "", CreateMockWalletDatabase());
+    {
+        LOCK2(wallet->cs_wallet, ::cs_main);
+        wallet->SetLastBlockProcessed(105, node.context()->chainman->ActiveChain().Tip()->GetBlockHash());
+    }
+
+    wallet->LoadWallet();
+    wallet->SetupLegacyScriptPubKeyMan();
+
+    // Initialize relevant QT models.
+    std::unique_ptr<const PlatformStyle> platformStyle(PlatformStyle::instantiate("other"));
+    OptionsModel optionsModel(node);
+    bilingual_str error;
+    QVERIFY(optionsModel.Init(error));
+    ClientModel clientModel(node, &optionsModel);
+    WalletContext& context = *node.walletLoader().context();
+    AddWallet(context, wallet);
+    WalletModel walletModel(interfaces::MakeWallet(context, wallet), clientModel, platformStyle.get());
+    RemoveWallet(context, wallet, /* load_on_start= */ std::nullopt);
+
+    ImportDialog importDialogPubkey(ImportDialog::importPubkey, &walletModel);
+    ImportDialog importDialogPrivkey(ImportDialog::importPrivkey, &walletModel);
+    ImportDialog importDialogAddress(ImportDialog::importAddress, &walletModel);
+
+    // Public key
+    Key key = BuildAddress(wallet.get());
+    ImportKeyData data;
+    data.key = key.pubkey;
+    EditKeyAndSubmit(&importDialogPubkey, ImportDialog::importPubkey, data, QString("Import Succeeded"));
+
+    AddressInfo addressInfo;
+    GetAddressInfo(wallet.get(), addressInfo, key.p2pkh_addr);
+    QCOMPARE(addressInfo.iswatchonly, true);
+    QCOMPARE(addressInfo.ismine, false);
+
+    // Public key + Label
+    key = BuildAddress(wallet.get());
+    data = ImportKeyData();
+    data.key = key.pubkey;
+    data.rescan = false;
+    data.label = "Successful public key import";
+    EditKeyAndSubmit(&importDialogPubkey, ImportDialog::importPubkey, data, QString("Import Succeeded"));
+
+    GetAddressInfo(wallet.get(), addressInfo, key.p2pkh_addr);
+    QCOMPARE(addressInfo.iswatchonly, true);
+    QCOMPARE(addressInfo.ismine, false);
+    QCOMPARE(addressInfo.label, "Successful public key import");
+
+    // Public key + Rescan
+    key = BuildAddress(wallet.get());
+    data = ImportKeyData();
+    data.key = key.pubkey;
+    EditKeyAndSubmit(&importDialogPubkey, ImportDialog::importPubkey, data, QString("Import Succeeded"));
+
+    GetAddressInfo(wallet.get(), addressInfo, key.p2pkh_addr);
+    QCOMPARE(addressInfo.iswatchonly, true);
+    QCOMPARE(addressInfo.ismine, false);
+
+    // Public key must be hex string
+    key = BuildAddress(wallet.get());
+    data = ImportKeyData();
+    data.key = key.p2pkh_addr;
+    EditKeyAndSubmit(&importDialogPubkey, ImportDialog::importPubkey, data, QString("Pubkey must be a hex string"));
+
+    // Public key not a valid public key
+    data = ImportKeyData();
+    data.key = "02e053f77836d086a6082f441fc0db6a71de0620f3e1c9797d80ade82979c73c";
+    EditKeyAndSubmit(&importDialogPubkey, ImportDialog::importPubkey, data, QString("Pubkey is not a valid public key"));
+
+    // Private key
+    key = BuildAddress(wallet.get());
+    data = ImportKeyData();
+    data.key = key.privkey;
+    EditKeyAndSubmit(&importDialogPrivkey, ImportDialog::importPrivkey, data, QString("Import Succeeded"));
+
+    GetAddressInfo(wallet.get(), addressInfo, key.p2pkh_addr);
+    QCOMPARE(addressInfo.iswatchonly, false);
+    QCOMPARE(addressInfo.ismine, true);
+
+    // Private key + Label
+    key = BuildAddress(wallet.get());
+    data = ImportKeyData();
+    data.key = key.privkey;
+    data.label = "Successful private key import";
+    EditKeyAndSubmit(&importDialogPrivkey, ImportDialog::importPrivkey, data, QString("Import Succeeded"));
+
+    GetAddressInfo(wallet.get(), addressInfo, key.p2pkh_addr);
+    QCOMPARE(addressInfo.iswatchonly, false);
+    QCOMPARE(addressInfo.ismine, true);
+    QCOMPARE(addressInfo.label, "Successful private key import");
+
+    // Private key not a valid public key
+    data = ImportKeyData();
+    data.key = "cSFUNyEbpxP6Jur5kJftYEugGzkd1QUjHwSwkjH5yco6z1oERCq";
+    EditKeyAndSubmit(&importDialogPrivkey, ImportDialog::importPrivkey, data, QString("Invalid private key encoding."));
+
+    // Address
+    key = BuildAddress(wallet.get());
+    data = ImportKeyData();
+    data.key = key.p2pkh_addr;
+    EditKeyAndSubmit(&importDialogAddress, ImportDialog::importAddress, data, QString("Import Succeeded"));
+
+    GetAddressInfo(wallet.get(), addressInfo, key.p2pkh_addr);
+    QCOMPARE(addressInfo.iswatchonly, true);
+    QCOMPARE(addressInfo.ismine, false);
+
+    // Address + Label
+    key = BuildAddress(wallet.get());
+    data = ImportKeyData();
+    data.key = key.p2pkh_addr;
+    data.label = "Successful address import";
+    EditKeyAndSubmit(&importDialogAddress, ImportDialog::importAddress, data, QString("Import Succeeded"));
+
+    GetAddressInfo(wallet.get(), addressInfo, key.p2pkh_addr);
+    QCOMPARE(addressInfo.iswatchonly, true);
+    QCOMPARE(addressInfo.ismine, false);
+    QCOMPARE(addressInfo.label, "Successful address import");
+
+    // Invalid Address or script
+    key = BuildAddress(wallet.get());
+    data = ImportKeyData();
+    data.key = key.privkey;
+    EditKeyAndSubmit(&importDialogAddress, ImportDialog::importAddress, data, QString("Invalid Bitcoin address or script"));
+
+    // Invalid Address can't import Bech32m into a legacy wallet
+    data = ImportKeyData();
+    data.key = "bcrt1p0xlxvlhemja6c4dqv22uapctqupfhlxm9h8z3k2e72q4k9hcz7vqc8gma6";
+    EditKeyAndSubmit(&importDialogAddress, ImportDialog::importAddress, data, QString("Bech32m addresses cannot be imported into legacy wallets"));
+
+    // Invalid Address use the p2sh flag with an address
+    key = BuildAddress(wallet.get());
+    data = ImportKeyData();
+    data.key = key.p2pkh_addr;
+    data.p2sh = true;
+    EditKeyAndSubmit(&importDialogAddress, ImportDialog::importAddress, data, QString("Cannot use the p2sh flag with an address - use a script instead"));
+}
+
+void ImportLegacyTests::importLegacyTests()
+{
+#ifdef Q_OS_MACOS
+    if (QApplication::platformName() == "minimal") {
+        // Disable for mac on "minimal" platform to avoid crashes inside the Qt
+        // framework when it tries to look up unimplemented cocoa functions,
+        // and fails to handle returned nulls
+        // (https://bugreports.qt.io/browse/QTBUG-49686).
+        QWARN("Skipping ImportLegacyTests on mac build with 'minimal' platform set due to Qt bugs. To run AppTests, invoke "
+              "with 'QT_QPA_PLATFORM=cocoa test_bitcoin-qt' on mac, or else use a linux or windows build.");
+        return;
+    }
+#endif
+    TestImportLegacy(m_node);
+}
\ No newline at end of file
diff --git a/src/qt/test/importlegacytests.h b/src/qt/test/importlegacytests.h
new file mode 100644
index 00000000000..4971173e964
--- /dev/null
+++ b/src/qt/test/importlegacytests.h
@@ -0,0 +1,27 @@
+// Copyright (c) 2023 The Bitcoin Core developers
+// Distributed under the MIT software license, see the accompanying
+// file COPYING or http://www.opensource.org/licenses/mit-license.php.
+
+#ifndef BITCOIN_QT_TEST_IMPORTLEGACYTESTS_H
+#define BITCOIN_QT_TEST_IMPORTLEGACYTESTS_H
+
+#include <QObject>
+#include <QTest>
+
+namespace interfaces {
+class Node;
+} // namespace interfaces
+
+class ImportLegacyTests : public QObject
+{
+public:
+    explicit ImportLegacyTests(interfaces::Node& node) : m_node(node) {}
+    interfaces::Node& m_node;
+
+    Q_OBJECT
+
+private Q_SLOTS:
+    void importLegacyTests();
+};
+
+#endif // BITCOIN_QT_TEST_IMPORTLEGACYTESTS_H
diff --git a/src/qt/test/test_main.cpp b/src/qt/test/test_main.cpp
index cd92c3d38b6..eff4b7f4f13 100644
--- a/src/qt/test/test_main.cpp
+++ b/src/qt/test/test_main.cpp
@@ -19,6 +19,7 @@
 #ifdef ENABLE_WALLET
 #include <qt/test/addressbooktests.h>
 #include <qt/test/importdescriptorstests.h>
+#include <qt/test/importlegacytests.h>
 #include <qt/test/importmultitests.h>
 #include <qt/test/wallettests.h>
 #endif // ENABLE_WALLET
@@ -112,6 +113,9 @@ int main(int argc, char* argv[])
 
     ImportDescriptorsTests test8(app.node());
     num_test_failures += QTest::qExec(&test8);
+
+    ImportLegacyTests test9(app.node());
+    num_test_failures += QTest::qExec(&test9);
 #endif
 
     if (num_test_failures) {