diff --git a/src/agent/ConsoleInput.cc b/src/agent/ConsoleInput.cc
index 3dda67c..20f116c 100644
--- a/src/agent/ConsoleInput.cc
+++ b/src/agent/ConsoleInput.cc
@@ -39,6 +39,7 @@
 #include "UnicodeEncoding.h"
 #include "Win32Console.h"
 
+// MAPVK_VK_TO_VSC isn't defined by the old MinGW.
 #ifndef MAPVK_VK_TO_VSC
 #define MAPVK_VK_TO_VSC 0
 #endif
@@ -596,6 +597,7 @@ void ConsoleInput::appendKeyPress(std::vector<INPUT_RECORD> &records,
     const bool ctrl = (keyState & LEFT_CTRL_PRESSED) != 0;
     const bool alt = (keyState & LEFT_ALT_PRESSED) != 0;
     const bool shift = (keyState & SHIFT_PRESSED) != 0;
+    const bool enhanced = (keyState & ENHANCED_KEY) != 0;
     bool hasDebugInput = false;
 
     if (isTracingEnabled()) {
@@ -642,6 +644,9 @@ void ConsoleInput::appendKeyPress(std::vector<INPUT_RECORD> &records,
         stepKeyState |= SHIFT_PRESSED;
         appendInputRecord(records, TRUE, VK_SHIFT, 0, stepKeyState);
     }
+    if (enhanced) {
+        stepKeyState |= ENHANCED_KEY;
+    }
     if (m_escapeInputEnabled) {
         reencodeEscapedKeyPress(records, virtualKey, codePoint, stepKeyState);
     } else {
@@ -658,6 +663,9 @@ void ConsoleInput::appendKeyPress(std::vector<INPUT_RECORD> &records,
         codePoint = 0;
     }
     appendCPInputRecords(records, FALSE, virtualKey, codePoint, stepKeyState);
+    if (enhanced) {
+        stepKeyState &= ~ENHANCED_KEY;
+    }
     if (shift) {
         stepKeyState &= ~SHIFT_PRESSED;
         appendInputRecord(records, FALSE, VK_SHIFT, 0, stepKeyState);
diff --git a/src/agent/DefaultInputMap.cc b/src/agent/DefaultInputMap.cc
index 186e324..b4dd7b4 100644
--- a/src/agent/DefaultInputMap.cc
+++ b/src/agent/DefaultInputMap.cc
@@ -206,6 +206,24 @@ const int kCsiShiftModifier = 1;
 const int kCsiAltModifier   = 2;
 const int kCsiCtrlModifier  = 4;
 
+static inline bool useEnhancedForVirtualKey(uint16_t vk) {
+    switch (vk) {
+        case VK_UP:
+        case VK_DOWN:
+        case VK_LEFT:
+        case VK_RIGHT:
+        case VK_INSERT:
+        case VK_DELETE:
+        case VK_HOME:
+        case VK_END:
+        case VK_PRIOR:
+        case VK_NEXT:
+            return true;
+        default:
+            return false;
+    }
+}
+
 static void addSimpleEntries(InputMap &inputMap) {
     struct SimpleEncoding {
         const char *encoding;
@@ -233,9 +251,13 @@ static void addSimpleEntries(InputMap &inputMap) {
     };
 
     for (size_t i = 0; i < DIM(simpleEncodings); ++i) {
+        auto k = simpleEncodings[i].key;
+        if (useEnhancedForVirtualKey(k.virtualKey)) {
+            k.keyState |= ENHANCED_KEY;
+        }
         inputMap.set(simpleEncodings[i].encoding,
                      strlen(simpleEncodings[i].encoding),
-                     simpleEncodings[i].key);
+                     k);
     }
 }
 
@@ -263,6 +285,9 @@ static inline void setEncoding(const ExpandContext &ctx, char *end,
                 break;
         }
     }
+    if (useEnhancedForVirtualKey(k.virtualKey)) {
+        k.keyState |= ENHANCED_KEY;
+    }
     ctx.inputMap.set(ctx.buffer, end - ctx.buffer, k);
 }