diff --git a/src/mode/modeHandler.ts b/src/mode/modeHandler.ts
index e28d037165d..d1acc424ec1 100644
--- a/src/mode/modeHandler.ts
+++ b/src/mode/modeHandler.ts
@@ -178,7 +178,25 @@ export class ModeHandler implements vscode.Disposable {
         // We shouldn't go to visual mode on any other mode, because the other visual modes are handled
         // very differently than vscode so only our extension will create them. And the other modes
         // like the plugin modes shouldn't be changed or else it might mess up the plugins actions.
+        this._logger.debug('Selections: Creating Multi Cursor Visual Selection!');
+        if (e.kind === vscode.TextEditorSelectionChangeKind.Keyboard) {
+          this.vimState.cursors = e.textEditor.selections.map(
+            (sel) =>
+              new Range(
+                Position.FromVSCodePosition(sel.anchor),
+                sel.anchor.isBefore(sel.active)
+                  ? // This is another case where we are changing our cursor so that the selection looks right
+                    Position.FromVSCodePosition(sel.active).getRight()
+                  : Position.FromVSCodePosition(sel.active)
+              )
+          );
+        }
         await this.setCurrentMode(Mode.Visual);
+        // Here we need our updateView to draw the selection because we want vscode to include the initial
+        // character, and by doing it through out updateView we make sure that any resultant selection
+        // change event will be ignored.
+        await this.updateView(this.vimState);
+        return;
       }
       return this.updateView(this.vimState);
     }
@@ -189,36 +207,55 @@ export class ModeHandler implements vscode.Disposable {
      */
     if (e.kind !== vscode.TextEditorSelectionChangeKind.Mouse) {
       if (selection) {
-        if (e.kind === vscode.TextEditorSelectionChangeKind.Command) {
-          // This 'Command' kind is triggered when using a command like 'editor.action.smartSelect.grow'
-          // but it is also triggered when we set the 'editor.selections' on 'updateView'.
-          if (
-            [Mode.Normal, Mode.Visual, Mode.Insert, Mode.Replace].includes(
-              this.vimState.currentMode
-            )
-          ) {
-            // Since the selections weren't ignored then probably we got change of selection from
-            // a command, so we need to update our start and stop positions. This is where commands
-            // like 'editor.action.smartSelect.grow' are handled.
-            if (this.vimState.currentMode === Mode.Visual) {
-              this._logger.debug('Selections: Updating Visual Selection!');
-              this.vimState.cursorStopPosition = Position.FromVSCodePosition(selection.active);
-              this.vimState.cursorStartPosition = Position.FromVSCodePosition(selection.anchor);
-              await this.updateView(this.vimState, { drawSelection: false, revealRange: false });
-              return;
-            } else if (!selection.active.isEqual(selection.anchor)) {
-              this._logger.debug('Selections: Creating Visual Selection from command!');
-              this.vimState.cursorStopPosition = Position.FromVSCodePosition(selection.active);
-              this.vimState.cursorStartPosition = Position.FromVSCodePosition(selection.anchor);
-              await this.setCurrentMode(Mode.Visual);
-              await this.updateView(this.vimState, { drawSelection: false, revealRange: false });
-              return;
+        if (
+          [Mode.Normal, Mode.Visual, Mode.Insert, Mode.Replace].includes(this.vimState.currentMode)
+        ) {
+          // Since the selections weren't ignored then probably we got change of selection from
+          // a command, so we need to update our start and stop positions. This is where commands
+          // like 'editor.action.smartSelect.grow' are handled.
+          if (this.vimState.currentMode === Mode.Visual) {
+            this._logger.debug('Selections: Updating Visual Selection!');
+            const active = Position.FromVSCodePosition(selection.active);
+            const anchor = Position.FromVSCodePosition(selection.anchor);
+            this.vimState.cursorStopPosition = active;
+            this.vimState.cursorStartPosition = anchor;
+            if (e.kind === vscode.TextEditorSelectionChangeKind.Keyboard) {
+              if (selection.anchor.isAfter(selection.active)) {
+                this.vimState.cursorStartPosition = anchor.getLeft();
+              }
+            }
+            // Here we need our updateView to draw the selection because even though we don't need to
+            // change the vscode selection, in some situations when you trigger an initial selection
+            // and then update that selection these events will be triggered only after vscode has done
+            // both selection changes and in that situation we will get all the events in a row and since
+            // when creating the visual selection the first time (the code block below this) we change
+            // the selection, then we need to change the selection on the updates as well or else we
+            // would revert the vscode selection back to the initial one. (This issue is noticeable when
+            // using the VSpaceCode extension that shows a QuickPick menu that allows you to call commands
+            // that change the selection in vscode, but we will only get this 'handleSelectionChange'
+            // function called with all those changes after the user closes the QuickPick menu)
+            await this.updateView(this.vimState);
+            return;
+          } else if (!selection.active.isEqual(selection.anchor)) {
+            this._logger.debug('Selections: Creating Visual Selection from command!');
+            const active = Position.FromVSCodePosition(selection.active);
+            const anchor = Position.FromVSCodePosition(selection.anchor);
+            this.vimState.cursorStopPosition = active;
+            this.vimState.cursorStartPosition = anchor;
+            if (e.kind === vscode.TextEditorSelectionChangeKind.Keyboard) {
+              if (selection.anchor.isBefore(selection.active)) {
+                // This is another case where we are changing our cursor so that the selection looks right
+                this.vimState.cursorStopPosition = active.getRight();
+              }
             }
+            await this.setCurrentMode(Mode.Visual);
+            // Here we need our updateView to draw the selection because we want vscode to include the
+            // initial character, and by doing it through out updateView we make sure that any resultant
+            // selection change event will be ignored.
+            await this.updateView(this.vimState);
+            return;
           }
         }
-        // Here we are on the selection changed of kind 'Keyboard' or 'undefined' which is triggered
-        // when pressing movement keys that are not caught on the 'type' override but also when using
-        // commands like 'cursorMove'.
 
         if (isVisualMode(this.vimState.currentMode)) {
           /**
diff --git a/test/mode/modeVisual.test.ts b/test/mode/modeVisual.test.ts
index 305f6373b71..349fd27201d 100644
--- a/test/mode/modeVisual.test.ts
+++ b/test/mode/modeVisual.test.ts
@@ -1667,4 +1667,426 @@ suite('Mode Visual', () => {
       endMode: Mode.Normal,
     });
   });
+
+  suite('Visual mode with commands cursorRightSelect, cursorLeftSelect in Insert Mode', () => {
+    newTest({
+      title: 'Command cursorRightSelect enters visual mode',
+      config: {
+        insertModeKeyBindings: [
+          {
+            before: ['<C-l>'],
+            commands: ['cursorRightSelect'],
+          },
+        ],
+      },
+      start: [
+        `"vim.normalModeKeyBindingsNonRecursive": [`,
+        `  {`,
+        `    "be|fore": ["j"],`,
+        `    "after": ["g", "j"],`,
+        `  },`,
+        `]`,
+      ],
+      keysPressed: 'i<C-l>d',
+      end: [
+        `"vim.normalModeKeyBindingsNonRecursive": [`,
+        `  {`,
+        `    "be|re": ["j"],`,
+        `    "after": ["g", "j"],`,
+        `  },`,
+        `]`,
+      ],
+      endMode: Mode.Normal,
+    });
+
+    newTest({
+      title: 'Command cursorLeftSelect enters visual mode',
+      config: {
+        insertModeKeyBindings: [
+          {
+            before: ['<C-h>'],
+            commands: ['cursorLeftSelect'],
+          },
+        ],
+      },
+      start: [
+        `"vim.normalModeKeyBindingsNonRecursive": [`,
+        `  {`,
+        `    "be|fore": ["j"],`,
+        `    "after": ["g", "j"],`,
+        `  },`,
+        `]`,
+      ],
+      keysPressed: 'i<C-h>d',
+      end: [
+        `"vim.normalModeKeyBindingsNonRecursive": [`,
+        `  {`,
+        `    "b|ore": ["j"],`,
+        `    "after": ["g", "j"],`,
+        `  },`,
+        `]`,
+      ],
+      endMode: Mode.Normal,
+    });
+
+    newTest({
+      title: 'Command cursorUpSelect enters visual mode',
+      config: {
+        insertModeKeyBindings: [
+          {
+            before: ['<C-k>'],
+            commands: ['cursorUpSelect'],
+          },
+        ],
+      },
+      start: [
+        `"vim.normalModeKeyBindingsNonRecursive": [`,
+        `  {`,
+        `    "be|fore": ["j"],`,
+        `    "after": ["g", "j"],`,
+        `  },`,
+        `]`,
+      ],
+      keysPressed: 'i<C-k>d',
+      end: [
+        `"vim.normalModeKeyBindingsNonRecursive": [`,
+        `  {|ore": ["j"],`,
+        `    "after": ["g", "j"],`,
+        `  },`,
+        `]`,
+      ],
+      endMode: Mode.Normal,
+    });
+
+    newTest({
+      title: 'Command cursorDownSelect enters visual mode',
+      config: {
+        insertModeKeyBindings: [
+          {
+            before: ['<C-j>'],
+            commands: ['cursorDownSelect'],
+          },
+        ],
+      },
+      start: [
+        `"vim.normalModeKeyBindingsNonRecursive": [`,
+        `  {`,
+        `    "be|fore": ["j"],`,
+        `    "after": ["g", "j"],`,
+        `  },`,
+        `]`,
+      ],
+      keysPressed: 'i<C-j>d',
+      end: [
+        `"vim.normalModeKeyBindingsNonRecursive": [`,
+        `  {`,
+        `    "be|er": ["g", "j"],`,
+        `  },`,
+        `]`,
+      ],
+      endMode: Mode.Normal,
+    });
+
+    newTest({
+      title: 'Command cursorRightSelect enters visual mode with multi cursors',
+      config: {
+        insertModeKeyBindings: [
+          {
+            before: ['<C-l>'],
+            commands: ['cursorRightSelect'],
+          },
+        ],
+      },
+      start: [
+        `"vim.normalModeKeyBindingsNonRecursive": [`,
+        `  {`,
+        `    "before": ["|j"],`,
+        `    "after": ["g", "j"],`,
+        `  },`,
+        `]`,
+      ],
+      keysPressed: 'vlgb_lll<Esc>i<C-l>d<Esc>',
+      end: [
+        `"vim.normalModeKeyBindingsNonRecursive": [`,
+        `  {`,
+        `    "be|re": ["j"],`,
+        `    "afr": ["g", "j"],`,
+        `  },`,
+        `]`,
+      ],
+      endMode: Mode.Normal,
+    });
+
+    newTest({
+      title: 'Command cursorLeftSelect enters visual mode with multi cursors',
+      config: {
+        insertModeKeyBindings: [
+          {
+            before: ['<C-h>'],
+            commands: ['cursorLeftSelect'],
+          },
+        ],
+      },
+      start: [
+        `"vim.normalModeKeyBindingsNonRecursive": [`,
+        `  {`,
+        `    "before": ["|j"],`,
+        `    "after": ["g", "j"],`,
+        `  },`,
+        `]`,
+      ],
+      keysPressed: 'vlgb_lll<Esc>i<C-h>d<Esc>',
+      end: [
+        `"vim.normalModeKeyBindingsNonRecursive": [`,
+        `  {`,
+        `    "b|ore": ["j"],`,
+        `    "aer": ["g", "j"],`,
+        `  },`,
+        `]`,
+      ],
+      endMode: Mode.Normal,
+    });
+  });
+
+  suite('Visual mode with commands cursorRightSelect, cursorLeftSelect in Normal Mode', () => {
+    newTest({
+      title: 'Command cursorRightSelect enters visual mode',
+      config: {
+        normalModeKeyBindings: [
+          {
+            before: ['<C-l>'],
+            commands: ['cursorRightSelect'],
+          },
+        ],
+      },
+      start: [
+        `"vim.normalModeKeyBindingsNonRecursive": [`,
+        `  {`,
+        `    "be|fore": ["j"],`,
+        `    "after": ["g", "j"],`,
+        `  },`,
+        `]`,
+      ],
+      keysPressed: '<C-l>d',
+      end: [
+        `"vim.normalModeKeyBindingsNonRecursive": [`,
+        `  {`,
+        `    "be|re": ["j"],`,
+        `    "after": ["g", "j"],`,
+        `  },`,
+        `]`,
+      ],
+      endMode: Mode.Normal,
+    });
+
+    newTest({
+      title: 'Command cursorLeftSelect enters visual mode',
+      config: {
+        normalModeKeyBindings: [
+          {
+            before: ['<C-h>'],
+            commands: ['cursorLeftSelect'],
+          },
+        ],
+      },
+      start: [
+        `"vim.normalModeKeyBindingsNonRecursive": [`,
+        `  {`,
+        `    "be|fore": ["j"],`,
+        `    "after": ["g", "j"],`,
+        `  },`,
+        `]`,
+      ],
+      keysPressed: '<C-h>d',
+      end: [
+        `"vim.normalModeKeyBindingsNonRecursive": [`,
+        `  {`,
+        `    "b|ore": ["j"],`,
+        `    "after": ["g", "j"],`,
+        `  },`,
+        `]`,
+      ],
+      endMode: Mode.Normal,
+    });
+
+    newTest({
+      title: 'Command cursorUpSelect enters visual mode',
+      config: {
+        normalModeKeyBindings: [
+          {
+            before: ['<C-k>'],
+            commands: ['cursorUpSelect'],
+          },
+        ],
+      },
+      start: [
+        `"vim.normalModeKeyBindingsNonRecursive": [`,
+        `  {`,
+        `    "be|fore": ["j"],`,
+        `    "after": ["g", "j"],`,
+        `  },`,
+        `]`,
+      ],
+      keysPressed: '<C-k>d',
+      end: [
+        `"vim.normalModeKeyBindingsNonRecursive": [`,
+        `  {|ore": ["j"],`,
+        `    "after": ["g", "j"],`,
+        `  },`,
+        `]`,
+      ],
+      endMode: Mode.Normal,
+    });
+
+    newTest({
+      title: 'Command cursorDownSelect enters visual mode',
+      config: {
+        normalModeKeyBindings: [
+          {
+            before: ['<C-j>'],
+            commands: ['cursorDownSelect'],
+          },
+        ],
+      },
+      start: [
+        `"vim.normalModeKeyBindingsNonRecursive": [`,
+        `  {`,
+        `    "be|fore": ["j"],`,
+        `    "after": ["g", "j"],`,
+        `  },`,
+        `]`,
+      ],
+      keysPressed: '<C-j>d',
+      end: [
+        `"vim.normalModeKeyBindingsNonRecursive": [`,
+        `  {`,
+        `    "be|er": ["g", "j"],`,
+        `  },`,
+        `]`,
+      ],
+      endMode: Mode.Normal,
+    });
+
+    newTest({
+      title: 'Command cursorRightSelect enters visual mode with multi cursors',
+      config: {
+        normalModeKeyBindings: [
+          {
+            before: ['<C-l>'],
+            commands: ['cursorRightSelect'],
+          },
+        ],
+      },
+      start: [
+        `"vim.normalModeKeyBindingsNonRecursive": [`,
+        `  {`,
+        `    "before": ["|j"],`,
+        `    "after": ["g", "j"],`,
+        `  },`,
+        `]`,
+      ],
+      keysPressed: 'vlgb_lll<Esc><C-l>d<Esc>',
+      end: [
+        `"vim.normalModeKeyBindingsNonRecursive": [`,
+        `  {`,
+        `    "be|re": ["j"],`,
+        `    "afr": ["g", "j"],`,
+        `  },`,
+        `]`,
+      ],
+      endMode: Mode.Normal,
+    });
+
+    newTest({
+      title: 'Command cursorLeftSelect enters visual mode with multi cursors',
+      config: {
+        normalModeKeyBindings: [
+          {
+            before: ['<C-h>'],
+            commands: ['cursorLeftSelect'],
+          },
+        ],
+      },
+      start: [
+        `"vim.normalModeKeyBindingsNonRecursive": [`,
+        `  {`,
+        `    "before": ["|j"],`,
+        `    "after": ["g", "j"],`,
+        `  },`,
+        `]`,
+      ],
+      keysPressed: 'vlgb_lll<Esc><C-h>d<Esc>',
+      end: [
+        `"vim.normalModeKeyBindingsNonRecursive": [`,
+        `  {`,
+        `    "b|ore": ["j"],`,
+        `    "aer": ["g", "j"],`,
+        `  },`,
+        `]`,
+      ],
+      endMode: Mode.Normal,
+    });
+
+    newTest({
+      title:
+        'Command cursorLeftSelect enters visual mode and next movement keeps anchor in right place',
+      config: {
+        normalModeKeyBindings: [
+          {
+            before: ['<C-h>'],
+            commands: ['cursorLeftSelect'],
+          },
+        ],
+      },
+      start: [
+        `"vim.normalModeKeyBindingsNonRecursive": [`,
+        `  {`,
+        `    "be|fore": ["j"],`,
+        `    "after": ["g", "j"],`,
+        `  },`,
+        `]`,
+      ],
+      keysPressed: '<C-h>hd',
+      end: [
+        `"vim.normalModeKeyBindingsNonRecursive": [`,
+        `  {`,
+        `    "|ore": ["j"],`,
+        `    "after": ["g", "j"],`,
+        `  },`,
+        `]`,
+      ],
+      endMode: Mode.Normal,
+    });
+
+    newTest({
+      title:
+        'Command cursorLeftSelect on multi cursors enters visual mode and next movement keeps anchor in right place',
+      config: {
+        normalModeKeyBindings: [
+          {
+            before: ['<C-h>'],
+            commands: ['cursorLeftSelect'],
+          },
+        ],
+      },
+      start: [
+        `"vim.normalModeKeyBindingsNonRecursive": [`,
+        `  {`,
+        `    "before": ["|j"],`,
+        `    "after": ["g", "j"],`,
+        `  },`,
+        `]`,
+      ],
+      keysPressed: 'vlgb_lll<Esc><C-h>hd<Esc>',
+      end: [
+        `"vim.normalModeKeyBindingsNonRecursive": [`,
+        `  {`,
+        `    "|ore": ["j"],`,
+        `    "er": ["g", "j"],`,
+        `  },`,
+        `]`,
+      ],
+      endMode: Mode.Normal,
+    });
+  });
 });