diff --git a/src/bitcoind.cpp b/src/bitcoind.cpp
index b8e67dccbc69f..6462e0e1deeaa 100644
--- a/src/bitcoind.cpp
+++ b/src/bitcoind.cpp
@@ -130,8 +130,10 @@ static bool ParseArgs(ArgsManager& args, int argc, char* argv[])
     }
 
     g_software_expiry = args.GetIntArg("-softwareexpiry", DEFAULT_SOFTWARE_EXPIRY);
-    if (IsThisSoftwareExpired(GetTime())) {
-        tfm::format(std::cerr, "This software is expired, and may be out of consensus. You must choose to upgrade or override this expiration.\n");
+    if (IsThisSoftwareExpiringSoon(GetTime())) {
+        tfm::format(std::cerr, "Warning: This software expires soon, and may fall out of consensus. You must choose to upgrade, or override this expiration with the 'softwareexpiry' option (Unix datetime, or 0 for no expiry).\n");
+    } else if (IsThisSoftwareExpired(GetTime())) {
+        tfm::format(std::cerr, "This software is expired, and may be out of consensus. You must choose to upgrade, or override this expiration with the 'softwareexpiry' option (Unix datetime, or 0 for no expiry).\n");
         exit(EXIT_FAILURE);
     }
 
diff --git a/src/clientversion.cpp b/src/clientversion.cpp
index 6bf7ef640661d..e6f87faad391c 100644
--- a/src/clientversion.cpp
+++ b/src/clientversion.cpp
@@ -113,3 +113,12 @@ bool IsThisSoftwareExpired(int64_t nTime)
     }
     return (nTime > g_software_expiry);
 }
+
+bool IsThisSoftwareExpiringSoon(int64_t ntime)
+{
+    if (g_software_expiry <= 0) {
+        return false;
+    }
+
+    return (ntime <= g_software_expiry && ntime > g_software_expiry - SOFTWARE_EXPIRY_WARN_PERIOD);
+}
diff --git a/src/clientversion.h b/src/clientversion.h
index 0d3fd033a37f9..c154ff29a6ae1 100644
--- a/src/clientversion.h
+++ b/src/clientversion.h
@@ -49,9 +49,14 @@ static constexpr int64_t SECONDS_PER_YEAR = 31558060;
 static constexpr int POSIX_EPOCH_YEAR = 1970;
 static constexpr int64_t DEFAULT_SOFTWARE_EXPIRY_OFFSET = 26784000;  // Around Nov 7
 static constexpr int64_t DEFAULT_SOFTWARE_EXPIRY = ((COPYRIGHT_YEAR - POSIX_EPOCH_YEAR) * SECONDS_PER_YEAR) + (SECONDS_PER_YEAR * 2) + DEFAULT_SOFTWARE_EXPIRY_OFFSET;
+
+static constexpr int64_t SECONDS_PER_WEEK = 604800;
+static constexpr int64_t SOFTWARE_EXPIRY_WARN_PERIOD = SECONDS_PER_WEEK * 4;
+
 extern int64_t g_software_expiry;
 
 bool IsThisSoftwareExpired(int64_t nTime);
+bool IsThisSoftwareExpiringSoon(int64_t nTime);
 
 #endif // WINDRES_PREPROC
 
diff --git a/src/qt/bitcoin.cpp b/src/qt/bitcoin.cpp
index f835ef62b3a94..ab772bd481152 100644
--- a/src/qt/bitcoin.cpp
+++ b/src/qt/bitcoin.cpp
@@ -53,6 +53,7 @@
 
 #include <QApplication>
 #include <QDebug>
+#include <QInputDialog>
 #include <QLatin1String>
 #include <QLibraryInfo>
 #include <QLocale>
@@ -654,9 +655,23 @@ int GuiMain(int argc, char* argv[])
     initTranslations(qtTranslatorBase, qtTranslator, translatorBase, translator);
 
     g_software_expiry = gArgs.GetIntArg("-softwareexpiry", DEFAULT_SOFTWARE_EXPIRY);
-    if (IsThisSoftwareExpired(GetTime())) {
-        QMessageBox::critical(nullptr, QObject::tr("Software expired"), QObject::tr("This software is expired, and may be out of consensus. You must choose to upgrade or override this expiration."));
-        return EXIT_FAILURE;
+    if (IsThisSoftwareExpiringSoon(GetTime())) {
+        QMessageBox::warning(nullptr, QObject::tr("Software expires soon"), QObject::tr("This software expires soon, and may fall out of consensus. You must choose to upgrade, or override this expiration with the 'softwareexpiry' option (Unix datetime, or 0 for no expiry)."));
+    } else if (IsThisSoftwareExpired(GetTime())) {
+        bool override_expiry_ok;
+        QString override_expiry = QInputDialog::getText(
+            nullptr,
+            QObject::tr("Software Expired"),
+            QObject::tr("This software is expired, and may be out of consensus.\nYou must choose to upgrade, or override this expiration by typing:\nI accept this software may be unsafe."),
+            QLineEdit::Normal,
+            "",
+            &override_expiry_ok);
+        if (!override_expiry_ok || override_expiry != QObject::tr("I accept this software may be unsafe.")) {
+            return EXIT_FAILURE;
+        }
+
+        gArgs.ModifyRWConfigFile("softwareexpiry", "0");
+        g_software_expiry = 0;
     }
 
 #ifdef ENABLE_WALLET
diff --git a/src/validation.cpp b/src/validation.cpp
index 388ba9de56af9..b90f66339b52a 100644
--- a/src/validation.cpp
+++ b/src/validation.cpp
@@ -4458,12 +4458,13 @@ static bool ContextualCheckBlockHeader(const CBlockHeader& block, BlockValidatio
     if (IsThisSoftwareExpired(block.nTime)) {
         // Wait an extra day before we start rejecting blocks
         CBlockIndex const *blockindex_old = pindexPrev;
-        for (int i = 0; i < 144; ++i) {
+        for (int i = 0; i < std::min(144, pindexPrev->nHeight); ++i) {
             assert(blockindex_old);
             blockindex_old = blockindex_old->pprev;
         }
         assert(blockindex_old);
         if (IsThisSoftwareExpired(blockindex_old->GetMedianTimePast())) {
+            chainman.GetNotifications().fatalError(_("This software is expired, and may be out of consensus. You must choose to upgrade, or override this expiration with the 'softwareexpiry' option (Unix datetime, or 0 for no expiry)."));
             return state.Invalid(BlockValidationResult::BLOCK_TIME_FUTURE, "node-expired", "node software has expired");
         }
     }