diff --git a/src/vs/editor/common/controller/cursorTypeOperations.ts b/src/vs/editor/common/controller/cursorTypeOperations.ts
index f7fde973b4e4bd097d9e3289157e46578bea6ff1..708a5e839090f9c7933d142ec4408cbb4bbf1f22 100644
--- a/src/vs/editor/common/controller/cursorTypeOperations.ts
+++ b/src/vs/editor/common/controller/cursorTypeOperations.ts
@@ -310,13 +310,34 @@ export class TypeOperations {
 
 		let lineText = model.getLineContent(range.startLineNumber);
 		let indentation = strings.getLeadingWhitespace(lineText).substring(0, range.startColumn - 1);
+
 		if (ir) {
-			if (/^\s+$/.test(lineText) || indentation === config.normalizeIndentation(ir.beforeEnter)) {
-				return TypeOperations._typeCommand(range, '\n' + config.normalizeIndentation(ir.afterEnter), keepPosition);
+			let beforeText = '\n';
+			let isSelectionEmpty = range.isEmpty();
+			if (indentation !== config.normalizeIndentation(ir.beforeEnter)) {
+				beforeText = config.normalizeIndentation(ir.beforeEnter) + lineText.substring(indentation.length, range.startColumn - 1) + '\n';
+				range = new Range(range.startLineNumber, 1, range.endLineNumber, range.endColumn);
+			}
+
+			let newLineContent = model.getLineContent(range.endLineNumber);
+			let oldEndColumn = CursorColumns.visibleColumnFromColumn2(config, model, range.getEndPosition());
+			if (!config.insertSpaces) {
+				oldEndColumn = Math.ceil(oldEndColumn / config.tabSize) + 1;
+			}
+			let firstNonWhitespace = strings.firstNonWhitespaceIndex(newLineContent);
+			if (firstNonWhitespace >= 0) {
+				range = range.setEndPosition(range.endLineNumber, Math.max(range.endColumn, firstNonWhitespace + 1));
+			} else {
+				range = range.setEndPosition(range.endLineNumber, model.getLineMaxColumn(range.endLineNumber));
 			}
-			let beforeText = config.normalizeIndentation(ir.beforeEnter) + lineText.substring(indentation.length, range.startColumn - 1);
-			range = new Range(range.startLineNumber, 1, range.endLineNumber, range.endColumn);
-			return TypeOperations._typeCommand(range, beforeText + '\n' + config.normalizeIndentation(ir.afterEnter), keepPosition);
+
+			if (keepPosition) {
+				return new ReplaceCommandWithoutChangingPosition(range, beforeText + config.normalizeIndentation(ir.afterEnter), true);
+			} else {
+				let offset = isSelectionEmpty ? oldEndColumn - config.normalizeIndentation(ir.afterEnter).length - 1 : 0;
+				return new ReplaceCommandWithOffsetCursorState(range, beforeText + config.normalizeIndentation(ir.afterEnter), 0, offset, true);
+			}
+
 		} else {
 			return TypeOperations._typeCommand(range, '\n' + config.normalizeIndentation(indentation), keepPosition);
 		}
diff --git a/src/vs/editor/common/modes/languageConfigurationRegistry.ts b/src/vs/editor/common/modes/languageConfigurationRegistry.ts
index b80e5bb60aa76d52bfa77a17d8d6fcc0ec29b24e..3fa864931d41389bc45f0fd6284b216191519e02 100644
--- a/src/vs/editor/common/modes/languageConfigurationRegistry.ts
+++ b/src/vs/editor/common/modes/languageConfigurationRegistry.ts
@@ -294,7 +294,7 @@ export class LanguageConfigurationRegistryImpl {
 					return resultLineNumber;
 				}
 				let text = model.getLineContent(lastLineNumber);
-				if (indentRulesSupport.shouldIgnore(text) || text === '') {
+				if (indentRulesSupport.shouldIgnore(text) || /^\s+$/.test(text) || text === '') {
 					resultLineNumber = lastLineNumber;
 					continue;
 				}