diff --git a/.vscode/tasks.json b/.vscode/tasks.json
index d18fb11e..c38a1946 100644
--- a/.vscode/tasks.json
+++ b/.vscode/tasks.json
@@ -15,7 +15,7 @@
     },
     {
       "type": "gulp",
-      "task": "build",
+      "task": "build-dev",
       "problemMatcher": []
     }
   ]
diff --git a/src/actions/commands/actions.ts b/src/actions/commands/actions.ts
index a5dcb277..2c568715 100644
--- a/src/actions/commands/actions.ts
+++ b/src/actions/commands/actions.ts
@@ -1529,17 +1529,35 @@ export class CommandInsertNewLineAbove extends BaseCommand {
     await vimState.setCurrentMode(Mode.Insert);
     const count = vimState.recordedState.count || 1;
 
+    const charPos = position.getLineBeginRespectingIndent(vimState.document).character;
+
     for (let i = 0; i < count; i++) {
       await vscode.commands.executeCommand('editor.action.insertLineBefore');
     }
 
     vimState.cursors = getCursorsAfterSync(vimState.editor);
-    for (let i = 0; i < count; i++) {
-      const newPos = new Position(
-        vimState.cursors[0].start.line + i,
-        vimState.cursors[0].start.character
-      );
+    const indentAmt = Math.max(charPos - vimState.cursors[0].start.character, 0);
+
+    const firstPos = new Position(vimState.cursors[0].start.line, charPos);
+    vimState.cursors[0] = new Cursor(firstPos, firstPos);
+    vimState.recordedState.transformer.addTransformation({
+      type: 'insertText',
+      text: TextEditor.setIndentationLevel('', indentAmt),
+      position: firstPos,
+      cursorIndex: 0,
+      manuallySetCursorPositions: true,
+    });
+
+    for (let i = 1; i < count; i++) {
+      const newPos = new Position(vimState.cursors[0].start.line + i, charPos);
       vimState.cursors.push(new Cursor(newPos, newPos));
+      vimState.recordedState.transformer.addTransformation({
+        type: 'insertText',
+        text: TextEditor.setIndentationLevel('', indentAmt),
+        position: newPos,
+        cursorIndex: i,
+        manuallySetCursorPositions: true,
+      });
     }
     vimState.cursors = vimState.cursors.reverse();
     vimState.isFakeMultiCursor = true;
diff --git a/test/actions/insertLine.test.ts b/test/actions/insertLine.test.ts
new file mode 100644
index 00000000..596599a5
--- /dev/null
+++ b/test/actions/insertLine.test.ts
@@ -0,0 +1,95 @@
+import * as assert from 'assert';
+import { Position, window } from 'vscode';
+import { getCurrentParagraphBeginning, getCurrentParagraphEnd } from '../../src/textobject/paragraph';
+import { WordType } from '../../src/textobject/word';
+import { TextEditor } from '../../src/textEditor';
+import { assertEqualLines, cleanUpWorkspace, setupWorkspace } from '../testUtils';
+import { ModeHandler } from '../../src/mode/modeHandler';
+import { getAndUpdateModeHandler } from '../../extension';
+import * as vscode from 'vscode';
+import { Configuration } from '../testConfiguration';
+
+suite('insertLineBefore', () => {
+  let modeHandler: ModeHandler;
+
+  suiteSetup(async () => {
+    const configuration = new Configuration();
+    configuration.tabstop = 4;
+    configuration.expandtab = true;
+
+    await setupWorkspace(configuration);
+    await setupWorkspace();
+    modeHandler = (await getAndUpdateModeHandler())!;
+  });
+
+  suiteTeardown(cleanUpWorkspace);
+
+  test('tabs are added to match previous line even if line above does not match', async () => {
+    // Setup the test
+    await modeHandler.handleMultipleKeyEvents(['<Esc>', 'g', 'g', 'd', 'G']);
+    await modeHandler.handleMultipleKeyEvents('i\na'.split(''));
+    await modeHandler.handleMultipleKeyEvents(['<Esc>']);
+    await modeHandler.handleMultipleKeyEvents('2G>>ob\nc'.split(''));
+
+    // This is the current state of the document
+    //
+    //    a
+    //    b
+    //    c
+    await modeHandler.handleMultipleKeyEvents(['<Esc>', '2', 'G', 'O', 'a']);
+    const text = vscode.window.activeTextEditor?.document.getText().split('\n');
+    assert.ok(text);
+    assert.strictEqual(text[1].replace(/[\n\r]/g, ''), text[2].replace(/[\n\r]/g, ''));
+  });
+
+  test('no extra whitespace added when insertLineBefore inserts correct amount', async () => {
+    await modeHandler.handleMultipleKeyEvents(['<Esc>', 'g', 'g', 'd', 'G']);
+    await modeHandler.handleMultipleKeyEvents('i\na'.split(''));
+    await modeHandler.handleMultipleKeyEvents(['<Esc>']);
+    await modeHandler.handleMultipleKeyEvents('2G>>ob\nc'.split(''));
+
+    // This is the current state of the document
+    //
+    //    a
+    //    b
+    //    c
+    await modeHandler.handleMultipleKeyEvents(['<Esc>', '3', 'G', 'O', 'b']);
+    const text = vscode.window.activeTextEditor?.document.getText().split('\n');
+    assert.ok(text);
+    assert.strictEqual(text[2].replace(/[\n\r]/g, ''), text[3].replace(/[\n\r]/g, ''));
+  });
+
+  test('works at the top of the document', async () => {
+    await modeHandler.handleMultipleKeyEvents(['<Esc>', 'g', 'g', 'd', 'G']);
+    await modeHandler.handleMultipleKeyEvents('ia'.split(''));
+    await modeHandler.handleMultipleKeyEvents(['<Esc>']);
+    await modeHandler.handleMultipleKeyEvents('gg>>'.split(''));
+
+    // This is the current state of the document
+    //    a
+    await modeHandler.handleMultipleKeyEvents(['<Esc>', 'g', 'g', 'O', 'a']);
+    const text = vscode.window.activeTextEditor?.document.getText().split('\n');
+    assert.ok(text);
+    assert.strictEqual(text[0].replace(/[\n\r]/g, ''), text[1].replace(/[\n\r]/g, ''));
+  });
+
+  test('works with multiple cursors', async () => {
+    await modeHandler.handleMultipleKeyEvents(['<Esc>', 'g', 'g', 'd', 'G']);
+    await modeHandler.handleMultipleKeyEvents('oa'.split(''));
+    await modeHandler.handleMultipleKeyEvents(['<Esc>']);
+    await modeHandler.handleMultipleKeyEvents('2G>>'.split(''));
+    // This is the current state of the document
+    //
+    //    a
+    await modeHandler.handleMultipleKeyEvents(['<Esc>', '2', 'G', '2', 'O', 'a']);
+    // After
+    //
+    //    a
+    //    a
+    //    a
+    const text = vscode.window.activeTextEditor?.document.getText().split('\n');
+    assert.ok(text);
+    assert.strictEqual(text[1].replace(/[\n\r]/g, ''), text[2].replace(/[\n\r]/g, ''));
+    assert.strictEqual(text[2].replace(/[\n\r]/g, ''), text[3].replace(/[\n\r]/g, ''));
+  });
+});