diff --git a/libs/s25main/WindowManager.cpp b/libs/s25main/WindowManager.cpp
index ae874f87bf..117484fc0d 100644
--- a/libs/s25main/WindowManager.cpp
+++ b/libs/s25main/WindowManager.cpp
@@ -136,8 +136,13 @@ void WindowManager::RelayKeyboardMessage(KeyboardMsgHandler msg, const KeyEvent&
         const auto itActiveWnd = std::find_if(windows.rbegin(), windows.rend(), [escape](const auto& wnd) {
             return !wnd->ShouldBeClosed() && !(escape && wnd->IsPinned());
         });
-        if(itActiveWnd != windows.rend() && (*itActiveWnd)->getCloseBehavior() != CloseBehavior::Custom)
-            (*itActiveWnd)->Close();
+        if(itActiveWnd != windows.rend())
+        {
+            if((*itActiveWnd)->getCloseBehavior() == CloseBehavior::Custom)
+                CALL_MEMBER_FN(**itActiveWnd, msg)(ke);
+            else
+                (*itActiveWnd)->Close();
+        }
     } else if(!CALL_MEMBER_FN(*windows.back(), msg)(ke)) // send to active window
     {
         // If not handled yet, relay to active window
diff --git a/libs/s25main/desktops/dskTest.cpp b/libs/s25main/desktops/dskTest.cpp
index 6b350cd8f4..5ef058cbac 100644
--- a/libs/s25main/desktops/dskTest.cpp
+++ b/libs/s25main/desktops/dskTest.cpp
@@ -16,6 +16,7 @@
 #include "desktops/dskTextureTest.h"
 #include "dskBenchmark.h"
 #include "files.h"
+#include "ingameWindows/iwMsgbox.h"
 #include "ogl/FontStyle.h"
 #include "s25util/colors.h"
 
@@ -36,7 +37,9 @@ enum
     ID_txtTest,
     ID_cbTxtSize,
     ID_btHideCtrls,
-    ID_btShowBenchmark
+    ID_btShowBenchmark,
+    ID_btPopupWarning,
+    ID_btPopupConfirm
 };
 }
 
@@ -91,6 +94,11 @@ dskTest::dskTest() : curBGIdx(LOAD_SCREENS.size())
     btPos.y += 11;
     AddText(ID_txtTest, btPos, "Enter something", COLOR_YELLOW, FontStyle::VCENTER, SmallFont);
 
+    AddTextButton(ID_btPopupWarning, DrawPoint(10, 260), Extent(150, 22), TextureColor::Green1, "Warning popup",
+                  NormalFont);
+    AddTextButton(ID_btPopupConfirm, DrawPoint(165, 260), Extent(150, 22), TextureColor::Green1, "Confirm popup",
+                  NormalFont);
+
     AddTextButton(ID_btDisable, DrawPoint(10, 540), Extent(150, 22), TextureColor::Green1, "Enable/Disable buttons",
                   NormalFont);
     AddTextButton(ID_btAnimate, DrawPoint(165, 540), Extent(80, 22), TextureColor::Green1, "Animate", NormalFont);
@@ -131,6 +139,26 @@ void dskTest::Msg_ButtonClick(const unsigned ctrl_id)
     {
         case ID_btTextureTest: WINDOWMANAGER.Switch(std::make_unique<dskTextureTest>()); break;
         case ID_btShowBenchmark: WINDOWMANAGER.Switch(std::make_unique<dskBenchmark>()); break;
+        case ID_btPopupWarning:
+            WINDOWMANAGER.Show(
+              std::make_unique<iwMsgbox>("Warning", "This addon may heavily alter intended map design.", this,
+                                         MsgboxConfig{{{"OK", MsgboxResult::Ok, TextureColor::Green2},
+                                                       {"Cancel", MsgboxResult::Cancel, TextureColor::Red1}},
+                                                      0,
+                                                      1,
+                                                      1},
+                                         MsgboxIcon::ExclamationRed, ID_btPopupWarning));
+            break;
+        case ID_btPopupConfirm:
+            WINDOWMANAGER.Show(
+              std::make_unique<iwMsgbox>("Confirm", "Do you want to continue?", this,
+                                         MsgboxConfig{{{"Yes", MsgboxResult::Yes, TextureColor::Green2},
+                                                       {"No", MsgboxResult::No, TextureColor::Red1}},
+                                                      0,
+                                                      1,
+                                                      1},
+                                         MsgboxIcon::QuestionRed, ID_btPopupConfirm));
+            break;
         case ID_btDisable:
             for(unsigned i = ID_grpBtStart; i < ID_grpBtEnd; i++)
             {
diff --git a/libs/s25main/ingameWindows/iwMsgbox.cpp b/libs/s25main/ingameWindows/iwMsgbox.cpp
index 927b6fae07..fcb968efb8 100644
--- a/libs/s25main/ingameWindows/iwMsgbox.cpp
+++ b/libs/s25main/ingameWindows/iwMsgbox.cpp
@@ -7,11 +7,12 @@
 #include "WindowManager.h"
 #include "controls/ctrlImage.h"
 #include "controls/ctrlMultiline.h"
+#include "driver/KeyEvent.h"
 #include "drivers/VideoDriverWrapper.h"
 #include "enum_cast.hpp"
-#include "helpers/EnumArray.h"
 #include "ogl/glArchivItem_Bitmap.h"
 #include "gameData/const_gui_ids.h"
+#include <utility>
 
 namespace {
 enum IDS
@@ -24,25 +25,96 @@ const Extent btSize(90, 20);
 const unsigned short paddingX = 15; /// Padding in X/to image
 const unsigned short minTextWidth = 150;
 const unsigned short maxTextHeight = 200;
+
+MsgboxConfig makeLegacyConfig(const MsgboxButton button)
+{
+    MsgboxConfig config;
+    switch(button)
+    {
+        case MsgboxButton::Ok:
+            config.buttons.push_back({_("OK"), MsgboxResult::Ok, TextureColor::Green2});
+            config.defaultButton = 0;
+            config.cancelButton = -1;
+            config.focusedButton = 0;
+            break;
+
+        case MsgboxButton::OkCancel:
+            config.buttons.push_back({_("OK"), MsgboxResult::Ok, TextureColor::Green2});
+            config.buttons.push_back({_("Cancel"), MsgboxResult::Cancel, TextureColor::Red1});
+            config.defaultButton = 0;
+            config.cancelButton = 1;
+            config.focusedButton = 1;
+            break;
+
+        case MsgboxButton::YesNo:
+            config.buttons.push_back({_("Yes"), MsgboxResult::Yes, TextureColor::Green2});
+            config.buttons.push_back({_("No"), MsgboxResult::No, TextureColor::Red1});
+            config.defaultButton = 0;
+            config.cancelButton = 1;
+            config.focusedButton = 1;
+            break;
+
+        case MsgboxButton::YesNoCancel:
+            config.buttons.push_back({_("Yes"), MsgboxResult::Yes, TextureColor::Green2});
+            config.buttons.push_back({_("No"), MsgboxResult::No, TextureColor::Red1});
+            config.buttons.push_back({_("Cancel"), MsgboxResult::Cancel, TextureColor::Grey});
+            config.defaultButton = 0;
+            config.cancelButton = 2;
+            config.focusedButton = 2;
+            break;
+    }
+    return config;
+}
 } // namespace
 
 iwMsgbox::iwMsgbox(const std::string& title, const std::string& text, Window* msgHandler, MsgboxButton button,
                    MsgboxIcon icon, unsigned msgboxid)
-    : iwMsgbox(title, text, msgHandler, button, "io", rttr::enum_cast(icon), msgboxid)
+    : iwMsgbox(title, text, msgHandler, makeLegacyConfig(button), icon, msgboxid)
 {}
 
 iwMsgbox::iwMsgbox(const std::string& title, const std::string& text, Window* msgHandler, MsgboxButton button,
                    const ResourceId& iconFile, unsigned iconIdx, unsigned msgboxid /* = 0 */)
+    : iwMsgbox(title, text, msgHandler, makeLegacyConfig(button), iconFile, iconIdx, msgboxid)
+{}
+
+iwMsgbox::iwMsgbox(const std::string& title, const std::string& text, Window* msgHandler, MsgboxConfig config,
+                   unsigned msgboxid /* = 0 */)
     : IngameWindow(CGI_MSGBOX, IngameWindow::posLastOrCenter, Extent(420, 140), title, LOADER.GetImageN("resource", 41),
                    true, CloseBehavior::Custom),
-      button(button), msgboxid(msgboxid), msgHandler_(msgHandler)
+      msgboxid(msgboxid), buttons_(std::move(config.buttons)), defaultButton_(config.defaultButton),
+      cancelButton_(config.cancelButton), focusedButton_(config.focusedButton), msgHandler_(msgHandler)
 {
-    Init(text, iconFile, iconIdx);
+    Init(text, nullptr);
 }
 
-void iwMsgbox::Init(const std::string& text, const ResourceId& iconFile, unsigned iconIdx)
+iwMsgbox::iwMsgbox(const std::string& title, const std::string& text, Window* msgHandler, MsgboxConfig config,
+                   MsgboxIcon icon, unsigned msgboxid)
+    : iwMsgbox(title, text, msgHandler, std::move(config), "io", rttr::enum_cast(icon), msgboxid)
+{}
+
+iwMsgbox::iwMsgbox(const std::string& title, const std::string& text, Window* msgHandler, MsgboxConfig config,
+                   const ResourceId& iconFile, unsigned iconIdx, unsigned msgboxid /* = 0 */)
+    : IngameWindow(CGI_MSGBOX, IngameWindow::posLastOrCenter, Extent(420, 140), title, LOADER.GetImageN("resource", 41),
+                   true, CloseBehavior::Custom),
+      msgboxid(msgboxid), buttons_(std::move(config.buttons)), defaultButton_(config.defaultButton),
+      cancelButton_(config.cancelButton), focusedButton_(config.focusedButton), msgHandler_(msgHandler)
+{
+    Init(text, LOADER.GetImageN(iconFile, iconIdx));
+}
+
+void iwMsgbox::Init(const std::string& text, glArchivItem_Bitmap* icon)
 {
-    glArchivItem_Bitmap* icon = LOADER.GetImageN(iconFile, iconIdx);
+    if(buttons_.empty())
+        buttons_.push_back({_("OK"), MsgboxResult::Ok, TextureColor::Green2});
+    if(buttons_.size() > 3)
+        buttons_.resize(3);
+    if(defaultButton_ >= buttons_.size())
+        defaultButton_ = 0;
+    if(cancelButton_ >= static_cast<int>(buttons_.size()))
+        cancelButton_ = -1;
+    if(focusedButton_ >= static_cast<int>(buttons_.size()))
+        focusedButton_ = -1;
+
     if(icon)
         AddImage(ID_ICON, contentOffset + DrawPoint(30, 20), icon);
     int textX = icon ? icon->getWidth() - icon->getNx() + GetCtrl<Window>(ID_ICON)->GetPos().x : contentOffset.x;
@@ -58,35 +130,17 @@ void iwMsgbox::Init(const std::string& text, const ResourceId& iconFile, unsigne
     // Increase window size if required
     SetIwSize(elMax(GetIwSize(), newIwSize));
 
-    unsigned defaultBt = 0;
-    // Buttons erstellen
-    switch(button)
+    const auto numButtons = static_cast<unsigned>(buttons_.size());
+    const int spacing = 6;
+    const int totalBtWidth = numButtons * btSize.x + (numButtons - 1) * spacing;
+    int x = GetSize().x / 2 - totalBtWidth / 2;
+    for(unsigned i = 0; i < numButtons; ++i)
     {
-        case MsgboxButton::Ok:
-            AddButton(ID_BT_0, GetSize().x / 2 - 45, _("OK"), TextureColor::Green2);
-            defaultBt = 0;
-            break;
-
-        case MsgboxButton::OkCancel:
-            AddButton(ID_BT_0, GetSize().x / 2 - 3 - 90, _("OK"), TextureColor::Green2);
-            AddButton(ID_BT_0 + 1, GetSize().x / 2 + 3, _("Cancel"), TextureColor::Red1);
-            defaultBt = 1;
-            break;
-
-        case MsgboxButton::YesNo:
-            AddButton(ID_BT_0, GetSize().x / 2 - 3 - 90, _("Yes"), TextureColor::Green2);
-            AddButton(ID_BT_0 + 1, GetSize().x / 2 + 3, _("No"), TextureColor::Red1);
-            defaultBt = 1;
-            break;
-
-        case MsgboxButton::YesNoCancel:
-            AddButton(ID_BT_0, GetSize().x / 2 - 45 - 6 - 90, _("Yes"), TextureColor::Green2);
-            AddButton(ID_BT_0 + 1, GetSize().x / 2 - 45, _("No"), TextureColor::Red1);
-            AddButton(ID_BT_0 + 2, GetSize().x / 2 + 45 + 6, _("Cancel"), TextureColor::Grey);
-            defaultBt = 2;
-            break;
+        AddButton(ID_BT_0 + i, x, buttons_[i].text, buttons_[i].color);
+        x += btSize.x + spacing;
     }
-    const Window* defBt = GetCtrl<Window>(defaultBt + ID_BT_0);
+    const unsigned focusedButton = focusedButton_ >= 0 ? static_cast<unsigned>(focusedButton_) : defaultButton_;
+    const Window* defBt = GetCtrl<Window>(focusedButton + ID_BT_0);
     if(defBt)
         VIDEODRIVER.SetMousePos(defBt->GetDrawPos() + DrawPoint(defBt->GetSize()) / 2);
     WINDOWMANAGER.SetCursor();
@@ -152,16 +206,25 @@ void iwMsgbox::MoveIcon(const DrawPoint& pos)
     }
 }
 
-constexpr helpers::EnumArray<std::array<MsgboxResult, 3>, MsgboxButton> RET_IDS = {
-  {{MsgboxResult::Ok},
-   {MsgboxResult::Ok, MsgboxResult::Cancel},
-   {MsgboxResult::Yes, MsgboxResult::No},
-   {MsgboxResult::Yes, MsgboxResult::No, MsgboxResult::Cancel}}};
+bool iwMsgbox::Msg_KeyDown(const KeyEvent& ke)
+{
+    if(ke.kt == KeyType::Return)
+    {
+        Msg_ButtonClick(ID_BT_0 + defaultButton_);
+        return true;
+    }
+    if(ke.kt == KeyType::Escape && cancelButton_ >= 0)
+    {
+        Msg_ButtonClick(ID_BT_0 + static_cast<unsigned>(cancelButton_));
+        return true;
+    }
+    return false;
+}
 
 void iwMsgbox::Msg_ButtonClick(const unsigned ctrl_id)
 {
     if(msgHandler_)
-        msgHandler_->Msg_MsgBoxResult(msgboxid, RET_IDS[button][ctrl_id - ID_BT_0]);
+        msgHandler_->Msg_MsgBoxResult(msgboxid, buttons_[ctrl_id - ID_BT_0].result);
     Close();
 }
 
diff --git a/libs/s25main/ingameWindows/iwMsgbox.h b/libs/s25main/ingameWindows/iwMsgbox.h
index 53dd37e8bd..ff65290ea2 100644
--- a/libs/s25main/ingameWindows/iwMsgbox.h
+++ b/libs/s25main/ingameWindows/iwMsgbox.h
@@ -5,18 +5,38 @@
 #pragma once
 
 #include "IngameWindow.h"
+#include <string>
+#include <vector>
+
+class glArchivItem_Bitmap;
 class ResourceId;
 class Window;
+struct KeyEvent;
+
+struct MsgboxButtonConfig
+{
+    std::string text;
+    MsgboxResult result;
+    TextureColor color;
+};
+
+struct MsgboxConfig
+{
+    std::vector<MsgboxButtonConfig> buttons;
+    unsigned defaultButton = 0;
+    int cancelButton = -1;
+    int focusedButton = -1;
+};
 
 class iwMsgbox : public IngameWindow
 {
-    /// Buttons, die auf der Box erscheinen sollen
-    MsgboxButton button;
     /// ID für die Msgbox, um unterschiedliche
     unsigned msgboxid;
 
-    /// Einzelne Stringzeilen, die durch die Umbrechung ggf. zu Stande kommen
-    std::vector<std::string> strings;
+    std::vector<MsgboxButtonConfig> buttons_;
+    unsigned defaultButton_;
+    int cancelButton_;
+    int focusedButton_;
 
     Window* msgHandler_;
 
@@ -25,6 +45,12 @@ class iwMsgbox : public IngameWindow
              MsgboxIcon icon, unsigned msgboxid = 0);
     iwMsgbox(const std::string& title, const std::string& text, Window* msgHandler, MsgboxButton button,
              const ResourceId& iconFile, unsigned iconIdx, unsigned msgboxid = 0);
+    iwMsgbox(const std::string& title, const std::string& text, Window* msgHandler, MsgboxConfig config,
+             unsigned msgboxid = 0);
+    iwMsgbox(const std::string& title, const std::string& text, Window* msgHandler, MsgboxConfig config,
+             MsgboxIcon icon, unsigned msgboxid = 0);
+    iwMsgbox(const std::string& title, const std::string& text, Window* msgHandler, MsgboxConfig config,
+             const ResourceId& iconFile, unsigned iconIdx, unsigned msgboxid = 0);
 
     ~iwMsgbox() override;
 
@@ -32,9 +58,10 @@ class iwMsgbox : public IngameWindow
     void MoveIcon(const DrawPoint& pos);
 
 private:
-    void Init(const std::string& text, const ResourceId& iconFile, unsigned iconIdx);
+    void Init(const std::string& text, glArchivItem_Bitmap* icon);
 
     void AddButton(unsigned short id, int x, const std::string& text, TextureColor tc);
 
+    bool Msg_KeyDown(const KeyEvent& ke) override;
     void Msg_ButtonClick(unsigned ctrl_id) override;
 };
diff --git a/tests/s25Main/UI/testIngameWindow.cpp b/tests/s25Main/UI/testIngameWindow.cpp
index 8ef7fc6e48..d59406a20a 100644
--- a/tests/s25Main/UI/testIngameWindow.cpp
+++ b/tests/s25Main/UI/testIngameWindow.cpp
@@ -11,10 +11,13 @@
 #include "controls/ctrlButton.h"
 #include "controls/ctrlComboBox.h"
 #include "controls/ctrlEdit.h"
+#include "controls/ctrlImage.h"
 #include "controls/ctrlOptionGroup.h"
 #include "controls/ctrlPercent.h"
 #include "controls/ctrlProgress.h"
+#include "controls/ctrlTextButton.h"
 #include "desktops/dskGameLobby.h"
+#include "driver/KeyEvent.h"
 #include "drivers/VideoDriverWrapper.h"
 #include "helpers/format.hpp"
 #include "ingameWindows/IngameWindow.h"
@@ -451,6 +454,62 @@ void WindowPositioning_testOne(IngameWindow& wnd, const char* context, const std
 }
 } // namespace
 
+namespace {
+class MsgboxResultCatcher : public Window
+{
+public:
+    MsgboxResultCatcher() : Window(nullptr, 1, DrawPoint(0, 0)) {}
+
+    void Msg_MsgBoxResult(unsigned msgbox_id, MsgboxResult mbr) override
+    {
+        id = msgbox_id;
+        result = mbr;
+    }
+
+    unsigned id = 0;
+    MsgboxResult result = MsgboxResult::Cancel;
+};
+} // namespace
+
+BOOST_AUTO_TEST_CASE(MsgboxCustomButtons)
+{
+    MsgboxResultCatcher handler;
+    {
+        iwMsgbox wnd("Custom", "Choose a custom result", &handler,
+                     MsgboxConfig{{{"Apply", MsgboxResult::Ok, TextureColor::Green2},
+                                   {"Later", MsgboxResult::No, TextureColor::Grey},
+                                   {"Abort", MsgboxResult::Cancel, TextureColor::Red1}},
+                                  0,
+                                  2},
+                     MsgboxIcon::QuestionRed, 42);
+
+        const auto buttons = wnd.GetCtrls<ctrlTextButton>();
+        BOOST_TEST_REQUIRE(buttons.size() == 3u);
+        BOOST_TEST(buttons[0]->GetText() == "Apply");
+        BOOST_TEST(buttons[1]->GetText() == "Later");
+        BOOST_TEST(buttons[2]->GetText() == "Abort");
+
+        static_cast<Window&>(wnd).Msg_KeyDown(KeyEvent(KeyType::Return));
+        BOOST_TEST(handler.id == 42u);
+        BOOST_TEST(static_cast<int>(handler.result) == static_cast<int>(MsgboxResult::Ok));
+        BOOST_TEST(wnd.ShouldBeClosed());
+    }
+    {
+        iwMsgbox wnd(
+          "Custom", "Escape should use the configured cancel button", &handler,
+          MsgboxConfig{
+            {{"Yes", MsgboxResult::Yes, TextureColor::Green2}, {"No", MsgboxResult::No, TextureColor::Red1}}, 0, 1},
+          43);
+
+        BOOST_TEST(wnd.GetCtrls<ctrlImage>().empty());
+
+        static_cast<Window&>(wnd).Msg_KeyDown(KeyEvent(KeyType::Escape));
+        BOOST_TEST(handler.id == 43u);
+        BOOST_TEST(static_cast<int>(handler.result) == static_cast<int>(MsgboxResult::No));
+        BOOST_TEST(wnd.ShouldBeClosed());
+    }
+}
+
 BOOST_AUTO_TEST_CASE(WindowPositioning)
 {
     VIDEODRIVER.ResizeScreen(VideoMode(800, 600), DisplayMode::Windowed);
diff --git a/tests/s25Main/UI/testWindowManager.cpp b/tests/s25Main/UI/testWindowManager.cpp
index aa1af96c05..f22a9b4d37 100644
--- a/tests/s25Main/UI/testWindowManager.cpp
+++ b/tests/s25Main/UI/testWindowManager.cpp
@@ -488,6 +488,7 @@ BOOST_FIXTURE_TEST_CASE(EscClosesWindow, uiHelper::Fixture)
     // ESC does not close non-user-closable windows
     wnd1 = &WINDOWMANAGER.Show(std::make_unique<TestIngameWnd>(CGI_HELP, false, CloseBehavior::Custom));
     BOOST_TEST_REQUIRE(WINDOWMANAGER.GetTopMostWindow() == wnd1);
+    MOCK_EXPECT(wnd1->Msg_KeyDown).once().returns(false);
     WINDOWMANAGER.Msg_KeyDown(evEsc);
     REQUIRE_WINDOW_ALIVE(wnd1);
     MOCK_EXPECT(wnd1->DrawContent).once();
@@ -496,6 +497,7 @@ BOOST_FIXTURE_TEST_CASE(EscClosesWindow, uiHelper::Fixture)
 
     wnd2 = &WINDOWMANAGER.Show(std::make_unique<TestIngameWnd>(CGI_HELP, true, CloseBehavior::Custom));
     BOOST_TEST_REQUIRE(WINDOWMANAGER.GetTopMostWindow() == wnd2);
+    MOCK_EXPECT(wnd2->Msg_KeyDown).once().returns(false);
     WINDOWMANAGER.Msg_KeyDown(evEsc);
     REQUIRE_WINDOW_ALIVE(wnd1);
     REQUIRE_WINDOW_ALIVE(wnd2);