diff --git a/src/blackconfig/buildconfig.cpp b/src/blackconfig/buildconfig.cpp
index e920e1c19..72bc98b50 100644
--- a/src/blackconfig/buildconfig.cpp
+++ b/src/blackconfig/buildconfig.cpp
@@ -97,6 +97,11 @@ namespace BlackConfig
         return QDateTime::currentDateTime() > getEol();
     }
 
+    int CBuildConfig::daysTillLifetimeExpiry()
+    {
+        return QDateTime::currentDateTime().daysTo(getEol());
+    }
+
     const QString boolToYesNo(bool v)
     {
         return v ? QStringLiteral("yes") : QStringLiteral("no");
diff --git a/src/blackconfig/buildconfig.h b/src/blackconfig/buildconfig.h
index 8cbf3f9cf..94c7ef350 100644
--- a/src/blackconfig/buildconfig.h
+++ b/src/blackconfig/buildconfig.h
@@ -109,6 +109,9 @@ namespace BlackConfig
         //! Lifetime ended?
         static bool isLifetimeExpired();
 
+        //! Days till lifetime end
+        static int daysTillLifetimeExpiry();
+
         //! Vatsim client id
         static int vatsimClientId(); // defined in buildconfig_gen.cpp.in
 
diff --git a/src/blackcore/application.cpp b/src/blackcore/application.cpp
index d7ae79086..0872ae238 100644
--- a/src/blackcore/application.cpp
+++ b/src/blackcore/application.cpp
@@ -1404,14 +1404,21 @@ namespace BlackCore
         // checks
         if (CBuildConfig::isLifetimeExpired())
         {
-            this->cmdLineErrorMessage("Program expired " + CBuildConfig::getEol().toString());
+            this->cmdLineErrorMessage("Program expired since " + CBuildConfig::getEol().date().toString(),
+                                      "This version is no longer supported and usable. You have to install a newer version.");
             return false;
         }
 
+        if(CBuildConfig::daysTillLifetimeExpiry() <= 30)
+        {
+            this->cmdLineWarningMessage("This version will expire in " + QString::number(CBuildConfig::daysTillLifetimeExpiry()) + " days!",
+                                            "You'll need to update swift in order to use it thereafter.");
+        }
+
         const QStringList verifyErrors = CDirectoryUtils::verifyRuntimeDirectoriesAndFiles();
         if (!verifyErrors.isEmpty() && !m_applicationInfo.isUnitTest())
         {
-            this->cmdLineErrorMessage("Missing runtime directories/files: " + verifyErrors.join(", "));
+            this->cmdLineErrorMessage("Missing runtime directories/files:", verifyErrors.join(", "));
             return false;
         }
 
@@ -1419,13 +1426,13 @@ namespace BlackCore
         const QStringList args(QCoreApplication::instance()->arguments());
         if (!m_parser.parse(args))
         {
-            this->cmdLineErrorMessage(m_parser.errorText());
+            this->cmdLineErrorMessage("Parser error:", m_parser.errorText());
             return false;
         }
 
         if (m_singleApplication && m_alreadyRunning && !this->skipSingleApplicationCheck())
         {
-            this->cmdLineErrorMessage("Program must only run once");
+            this->cmdLineErrorMessage("Program must only run once", "You cannot run two or more instances side-by-side.");
             return false;
         }
 
@@ -1461,12 +1468,16 @@ namespace BlackCore
         return !this->synchronizeSetup(timeoutMs).hasErrorMessages();
     }
 
-    bool CApplication::cmdLineErrorMessage(const QString &errorMessage, bool retry) const
+    bool CApplication::cmdLineWarningMessage(const QString &text, const QString &informativeText) const
+    {
+        fputs(qPrintable(text + informativeText), stderr);
+        return false;
+    }
+
+    bool CApplication::cmdLineErrorMessage(const QString &text, const QString &informativeText, bool retry) const
     {
         Q_UNUSED(retry) // only works with UI version
-        fputs(qPrintable(errorMessage), stderr);
-        fputs("\n\n", stderr);
-        fputs(qPrintable(m_parser.helpText()), stderr);
+        fputs(qPrintable(text + informativeText), stderr);
         return false;
     }
 
diff --git a/src/blackcore/application.h b/src/blackcore/application.h
index 2b8dbc6cd..c4b6533d7 100644
--- a/src/blackcore/application.h
+++ b/src/blackcore/application.h
@@ -299,8 +299,11 @@ namespace BlackCore
         //! \see synchronizeSetup
         virtual bool parseAndSynchronizeSetup(int timeoutMs = BlackMisc::Network::CNetworkUtils::getLongTimeoutMs());
 
+        //! Display warning message
+        virtual bool cmdLineWarningMessage(const QString &text, const QString &informativeText = "") const;
+
         //! Display error message
-        virtual bool cmdLineErrorMessage(const QString &cmdLineErrorMessage, bool retry = false) const;
+        virtual bool cmdLineErrorMessage(const QString &text, const QString &informativeText = "", bool retry = false) const;
 
         //! Display error message
         virtual bool cmdLineErrorMessage(const BlackMisc::CStatusMessageList &msgs, bool retry = false) const;
diff --git a/src/blackcore/setupreader.cpp b/src/blackcore/setupreader.cpp
index 722034a7c..0b14b5a20 100644
--- a/src/blackcore/setupreader.cpp
+++ b/src/blackcore/setupreader.cpp
@@ -184,7 +184,7 @@ namespace BlackCore
                             ok = true;
                             break;
                         }
-                        retry = sApp->cmdLineErrorMessage(QStringLiteral("URL '%1' not reachable").arg(urlString), true);
+                        retry = sApp->cmdLineErrorMessage(QStringLiteral("URL '%1' not reachable").arg(urlString), "", true);
                     }
                     while (retry);
                 }
diff --git a/src/blackgui/guiapplication.cpp b/src/blackgui/guiapplication.cpp
index e4a11fbb5..ec26957ef 100644
--- a/src/blackgui/guiapplication.cpp
+++ b/src/blackgui/guiapplication.cpp
@@ -590,26 +590,27 @@ namespace BlackGui
         return "1.0";
     }
 
-    bool CGuiApplication::cmdLineErrorMessage(const QString &errorMessage, bool retry) const
+    bool CGuiApplication::cmdLineWarningMessage(const QString &text, const QString &informativeText) const
     {
-        const QString helpText(beautifyHelpMessage(m_parser.helpText()));
-        constexpr int MaxLength = 60;
+        QMessageBox warningBox(QMessageBox::Warning, QGuiApplication::applicationDisplayName(), "<b>" +text + "</b>");
+        warningBox.setInformativeText(informativeText);
+        return warningBox.exec();
+    }
 
-        QString htmlMsg;
-        if (errorMessage.length() > MaxLength)
-        {
-            htmlMsg = "<html><head/><body><h4>" + errorMessage.left(MaxLength) + "..." + "</h4>" +
-                      "Details: " + errorMessage + "<br><br>";
-        }
+    bool CGuiApplication::cmdLineErrorMessage(const QString &text, const QString &informativeText, bool retry) const
+    {
+        QMessageBox errorBox(QMessageBox::Critical, QGuiApplication::applicationDisplayName(), "<b>" +text + "</b>");
+        if(informativeText.length() < 300)
+            errorBox.setInformativeText(informativeText);
         else
-        {
-            htmlMsg = "<html><head/><body><h4>" + errorMessage + "</h4>";
-        }
-        htmlMsg += helpText + "</body></html>";
+            errorBox.setDetailedText(informativeText);
+
+        errorBox.addButton(QMessageBox::Abort);
+        if(retry)
+            errorBox.addButton(QMessageBox::Retry);
+
+        const int r = errorBox.exec();
 
-        const int r = QMessageBox::warning(nullptr,
-                                           QGuiApplication::applicationDisplayName(),
-                                           htmlMsg, QMessageBox::Abort, retry ? QMessageBox::Retry : QMessageBox::NoButton);
         return (r == QMessageBox::Retry);
     }
 
@@ -619,11 +620,10 @@ namespace BlackGui
         if (!msgs.hasErrorMessages()) { return false; }
         static const CPropertyIndexList propertiesSingle({ CStatusMessage::IndexMessage });
         static const CPropertyIndexList propertiesMulti({ CStatusMessage::IndexSeverityAsString, CStatusMessage::IndexMessage });
-        const QString helpText(CGuiApplication::beautifyHelpMessage(m_parser.helpText()));
         const QString msgsHtml = msgs.toHtml(msgs.size() > 1 ? propertiesMulti : propertiesSingle);
         const int r = QMessageBox::critical(nullptr,
                                             QGuiApplication::applicationDisplayName(),
-                                            "<html><head><body>" + msgsHtml + "<br><br>" + helpText + "</body></html>", QMessageBox::Abort, retry ? QMessageBox::Retry : QMessageBox::NoButton);
+                                            "<html><head><body>" + msgsHtml + "</body></html>", QMessageBox::Abort, retry ? QMessageBox::Retry : QMessageBox::NoButton);
         return (r == QMessageBox::Retry);
     }
 
diff --git a/src/blackgui/guiapplication.h b/src/blackgui/guiapplication.h
index c6caa9f4d..e7e26d8ed 100644
--- a/src/blackgui/guiapplication.h
+++ b/src/blackgui/guiapplication.h
@@ -125,9 +125,14 @@ namespace BlackGui
         //! Set window title
         QString setExtraWindowTitle(const QString &extraInfo, QWidget *mainWindowWidget = mainApplicationWidget()) const;
 
+        //! \name print warning message
+        //! @{
+        virtual bool cmdLineWarningMessage(const QString &text, const QString &informativeText) const override;
+        //! @}
+
         //! \name print messages generated during parsing / cmd handling
         //! @{
-        virtual bool cmdLineErrorMessage(const QString &cmdLineErrorMessage, bool retry = false) const override;
+        virtual bool cmdLineErrorMessage(const QString &text, const QString &informativeText = "", bool retry = false) const override;
         virtual bool cmdLineErrorMessage(const BlackMisc::CStatusMessageList &msgs, bool retry = false) const override;
         //! @}