diff --git a/src/host/screenInfo.cpp b/src/host/screenInfo.cpp
index 815e1f808ca..c1c9b536626 100644
--- a/src/host/screenInfo.cpp
+++ b/src/host/screenInfo.cpp
@@ -1455,6 +1455,7 @@ bool SCREEN_INFORMATION::IsMaximizedY() const
         const short cursorHeightInViewportAfter = newCursor.GetPosition().Y - _viewport.Top();
         COORD coordCursorHeightDiff = { 0 };
         coordCursorHeightDiff.Y = cursorHeightInViewportAfter - cursorHeightInViewportBefore;
+
         LOG_IF_FAILED(SetViewportOrigin(false, coordCursorHeightDiff, true));
 
         _textBuffer.swap(newTextBuffer);
@@ -1476,7 +1477,6 @@ bool SCREEN_INFORMATION::IsMaximizedY() const
             if (foundWrappedLine || charRow.WasWrapForced())
             {
                 foundWrappedLine = true;
-                _renderTarget.TriggerRedraw(Viewport::FromDimensions({ 0, y }, _viewport.Width(), 1));
             }
         }
     }
diff --git a/src/renderer/vt/XtermEngine.cpp b/src/renderer/vt/XtermEngine.cpp
index 2c1d8a08ed1..f652ceb3d52 100644
--- a/src/renderer/vt/XtermEngine.cpp
+++ b/src/renderer/vt/XtermEngine.cpp
@@ -19,7 +19,7 @@ XtermEngine::XtermEngine(_In_ wil::unique_hfile hPipe,
     _ColorTable(ColorTable),
     _cColorTable(cColorTable),
     _fUseAsciiOnly(fUseAsciiOnly),
-    _previousLineWrapped(false),
+    // _previousLineWrapped(false),
     _usingUnderLine(false),
     _needToDisableCursor(false),
     _lastCursorIsVisible(false),
@@ -235,6 +235,8 @@ XtermEngine::XtermEngine(_In_ wil::unique_hfile hPipe,
 {
     HRESULT hr = S_OK;
 
+    _trace.TraceMoveCursor(coord);
+
     if (coord.X != _lastText.X || coord.Y != _lastText.Y)
     {
         if (coord.X == 0 && coord.Y == 0)
@@ -248,8 +250,15 @@ XtermEngine::XtermEngine(_In_ wil::unique_hfile hPipe,
 
             // If the previous line wrapped, then the cursor is already at this
             //      position, we just don't know it yet. Don't emit anything.
-            if (_previousLineWrapped)
+            bool previousLineWrapped = false;
+            if (_wrappedRow.has_value())
+            {
+                previousLineWrapped = coord.Y == _wrappedRow.value() + 1;
+            }
+
+            if (previousLineWrapped)
             {
+                _trace.TraceWrapped();
                 hr = S_OK;
             }
             else
@@ -298,6 +307,9 @@ XtermEngine::XtermEngine(_In_ wil::unique_hfile hPipe,
         _newBottomLine = false;
     }
     _deferredCursorPos = INVALID_COORDS;
+
+    _wrappedRow = std::nullopt;
+
     return hr;
 }
 
diff --git a/src/renderer/vt/paint.cpp b/src/renderer/vt/paint.cpp
index 920dc86aeb2..bda79f6197a 100644
--- a/src/renderer/vt/paint.cpp
+++ b/src/renderer/vt/paint.cpp
@@ -376,8 +376,6 @@ using namespace Microsoft::Console::Types;
         return S_OK;
     }
 
-    RETURN_IF_FAILED(_MoveCursor(coord));
-
     std::wstring unclusteredString;
     unclusteredString.reserve(clusters.size());
     short totalWidth = 0;
@@ -445,10 +443,37 @@ using namespace Microsoft::Console::Types;
                                      (totalWidth - numSpaces) :
                                      totalWidth;
 
+    if (cchActual == 0)
+    {
+        // If the previous row wrapped, but this line is empty, then we actually
+        // do want to move the cursor down. Otherwise, we'll possibly end up
+        // accidentally erasing the last character from the previous line, as
+        // the cursor is still waiting on that character for the next character
+        // to follow it.
+        _wrappedRow = std::nullopt;
+        // TODO:<Before PR>: Write a test that emulates ~/vttests/reflow-120.py
+        // TODO:<Before PR>: Write a test that emulates ~/vttests/reflow-advanced.py
+    }
+
+    // Move the cursor to the start of this run.
+    RETURN_IF_FAILED(_MoveCursor(coord));
+
     // Write the actual text string
     std::wstring wstr = std::wstring(unclusteredString.data(), cchActual);
     RETURN_IF_FAILED(VtEngine::_WriteTerminalUtf8(wstr));
 
+    // If we've written text to the last column of the viewport, then mark
+    // that we've wrapped this line. The next time we attempt to move the
+    // cursor, if we're trying to move it to the start of the next line,
+    // we'll remember that this line was wrapped, and not manually break the
+    // line.
+    // Don't do this is the last character we're writing is a space - The last
+    // char will always be a space, but if we see that, we shouldn't wrap.
+    if ((_lastText.X + (totalWidth - numSpaces)) > _lastViewport.RightInclusive())
+    {
+        _wrappedRow = coord.Y;
+    }
+
     // Update our internal tracker of the cursor's position.
     // See MSFT:20266233
     // If the cursor is at the rightmost column of the terminal, and we write a
diff --git a/src/renderer/vt/tracing.cpp b/src/renderer/vt/tracing.cpp
index 3c5f4e0aa63..04c8d54c8b5 100644
--- a/src/renderer/vt/tracing.cpp
+++ b/src/renderer/vt/tracing.cpp
@@ -210,3 +210,30 @@ void RenderTracing::TraceLastText(const COORD lastTextPos) const
     UNREFERENCED_PARAMETER(lastTextPos);
 #endif UNIT_TESTING
 }
+
+void RenderTracing::TraceMoveCursor(const COORD pos) const
+{
+#ifndef UNIT_TESTING
+    const auto lastTextStr = _CoordToString(pos);
+    const auto cursor = lastTextStr.c_str();
+    TraceLoggingWrite(g_hConsoleVtRendererTraceProvider,
+                      "VtEngine_TraceMoveCursor",
+                      TraceLoggingString(cursor),
+                      TraceLoggingLevel(WINEVENT_LEVEL_VERBOSE));
+#else
+    UNREFERENCED_PARAMETER(pos);
+#endif UNIT_TESTING
+}
+
+void RenderTracing::TraceWrapped() const
+{
+#ifndef UNIT_TESTING
+    const auto* const msg = "Wrapped instead of \\r\\n";
+    TraceLoggingWrite(g_hConsoleVtRendererTraceProvider,
+                      "VtEngine_TraceWrapped",
+                      TraceLoggingString(msg),
+                      TraceLoggingLevel(WINEVENT_LEVEL_VERBOSE));
+#else
+    UNREFERENCED_PARAMETER(pos);
+#endif UNIT_TESTING
+}
diff --git a/src/renderer/vt/tracing.hpp b/src/renderer/vt/tracing.hpp
index 8d923adc813..ef00bea81be 100644
--- a/src/renderer/vt/tracing.hpp
+++ b/src/renderer/vt/tracing.hpp
@@ -29,6 +29,8 @@ namespace Microsoft::Console::VirtualTerminal
         void TraceString(const std::string_view& str) const;
         void TraceInvalidate(const Microsoft::Console::Types::Viewport view) const;
         void TraceLastText(const COORD lastText) const;
+        void TraceMoveCursor(const COORD pos) const;
+        void TraceWrapped() const;
         void TraceInvalidateAll(const Microsoft::Console::Types::Viewport view) const;
         void TraceTriggerCircling(const bool newFrame) const;
         void TraceStartPaint(const bool quickReturn,
diff --git a/src/renderer/vt/vtrenderer.hpp b/src/renderer/vt/vtrenderer.hpp
index cedd2722f53..ade20e90c1b 100644
--- a/src/renderer/vt/vtrenderer.hpp
+++ b/src/renderer/vt/vtrenderer.hpp
@@ -144,6 +144,8 @@ namespace Microsoft::Console::Render
         Microsoft::Console::VirtualTerminal::RenderTracing _trace;
         bool _inResizeRequest{ false };
 
+        std::optional<short> _wrappedRow{ std::nullopt };
+
         [[nodiscard]] HRESULT _Write(std::string_view const str) noexcept;
         [[nodiscard]] HRESULT _WriteFormattedString(const std::string* const pFormat, ...) noexcept;
         [[nodiscard]] HRESULT _Flush() noexcept;