diff --git a/src/mode/modeHandler.ts b/src/mode/modeHandler.ts
index 65cda981674..b6d37257c60 100644
--- a/src/mode/modeHandler.ts
+++ b/src/mode/modeHandler.ts
@@ -1362,13 +1362,19 @@ export class ModeHandler implements vscode.Disposable {
 
           selections = [ new vscode.Selection(start, stop) ];
         } else if (vimState.currentMode === ModeName.VisualLine) {
-          selections = [ new vscode.Selection(
+          selections = [new vscode.Selection(
             Position.EarlierOf(start, stop).getLineBegin(),
             Position.LaterOf(start, stop).getLineEnd()
-          ) ];
-          vimState.cursorStartPosition = selections[0].start as Position;
-          vimState.cursorPosition = selections[0].end as Position;
+          )];
 
+          // Maintain cursor position based on which direction the selection is going
+          if (start.line <= stop.line) {
+            vimState.cursorStartPosition = selections[0].start as Position;
+            vimState.cursorPosition = selections[0].end as Position;
+          } else {
+            vimState.cursorStartPosition = selections[0].end as Position;
+            vimState.cursorPosition = selections[0].start as Position;
+          }
         } else if (vimState.currentMode === ModeName.VisualBlock) {
           selections = [];
 
diff --git a/test/mode/modeVisualLine.test.ts b/test/mode/modeVisualLine.test.ts
index f6ce347abb3..453cc361aa1 100644
--- a/test/mode/modeVisualLine.test.ts
+++ b/test/mode/modeVisualLine.test.ts
@@ -308,6 +308,14 @@ suite("Mode Visual", () => {
       end: ["|11111111111111111111111", "11111111111111111111111"],
       endMode: ModeName.Normal
     });
+
+    newTestOnly({
+      title: "Can do a multi visual line replace from the bottom up",
+      start: ["test", "test", "test", "|test", "test"],
+      keysPressed: "Vkkr1",
+      end: ["test", "|1111", "1111", "1111", "test"],
+      endMode: ModeName.Normal
+    });
   });
 
 });