diff --git a/src/vs/editor/common/commands/shiftCommand.ts b/src/vs/editor/common/commands/shiftCommand.ts
index 3c0c9bea6fb29..3135f9e82c270 100644
--- a/src/vs/editor/common/commands/shiftCommand.ts
+++ b/src/vs/editor/common/commands/shiftCommand.ts
@@ -50,10 +50,12 @@ export class ShiftCommand implements ICommand {
 			const indentCount = desiredTabStop / indentSize; // will be an integer
 			return cachedStringRepeat(indent, indentCount);
 		} else {
-			const indent = '\t';
-			const desiredTabStop = CursorColumns.prevRenderTabStop(contentStartVisibleColumn, tabSize);
-			const indentCount = desiredTabStop / tabSize; // will be an integer
-			return cachedStringRepeat(indent, indentCount);
+			const desiredTabStop = CursorColumns.prevRenderTabStop(contentStartVisibleColumn, indentSize);
+			const tabCount = Math.floor(desiredTabStop / tabSize);
+			const spaceCount = desiredTabStop - tabCount * tabSize;
+			const tabString = cachedStringRepeat('\t', tabCount);
+			const spaceString = cachedStringRepeat(' ', spaceCount);
+			return tabString + spaceString;
 		}
 	}
 
@@ -67,10 +69,12 @@ export class ShiftCommand implements ICommand {
 			const indentCount = desiredTabStop / indentSize; // will be an integer
 			return cachedStringRepeat(indent, indentCount);
 		} else {
-			const indent = '\t';
-			const desiredTabStop = CursorColumns.nextRenderTabStop(contentStartVisibleColumn, tabSize);
-			const indentCount = desiredTabStop / tabSize; // will be an integer
-			return cachedStringRepeat(indent, indentCount);
+			const desiredTabStop = CursorColumns.nextRenderTabStop(contentStartVisibleColumn, indentSize);
+			const tabCount = Math.floor(desiredTabStop / tabSize);
+			const spaceCount = desiredTabStop - tabCount * tabSize;
+			const tabString = cachedStringRepeat('\t', tabCount);
+			const spaceString = cachedStringRepeat(' ', spaceCount);
+			return tabString + spaceString;
 		}
 	}
 
diff --git a/src/vs/editor/common/cursor/cursorTypeOperations.ts b/src/vs/editor/common/cursor/cursorTypeOperations.ts
index e735c14056f35..7d9e4c1a7930a 100644
--- a/src/vs/editor/common/cursor/cursorTypeOperations.ts
+++ b/src/vs/editor/common/cursor/cursorTypeOperations.ts
@@ -200,18 +200,32 @@ export class TypeOperations {
 		return indentation;
 	}
 
-	private static _replaceJumpToNextIndent(config: CursorConfiguration, model: ICursorSimpleModel, selection: Selection, insertsAutoWhitespace: boolean): ReplaceCommand {
+	private static _replaceJumpToNextIndent(config: CursorConfiguration, model: ICursorSimpleModel, selection: Selection, insertsAutoWhitespace: boolean): ICommand {
 		let typeText = '';
 
-		const position = selection.getStartPosition();
 		if (config.insertSpaces) {
-			const visibleColumnFromColumn = config.visibleColumnFromColumn(model, position);
+			const visibleColumnFromColumn = config.visibleColumnFromColumn(model, selection.getStartPosition());
 			const indentSize = config.indentSize;
 			const spacesCnt = indentSize - (visibleColumnFromColumn % indentSize);
 			for (let i = 0; i < spacesCnt; i++) {
 				typeText += ' ';
 			}
 		} else {
+			if (config.tabSize > config.indentSize) {
+				// If configured for mixed indentation and selection is at the front, do a shift instead,
+				// which will properly normalize existing leading whitespace
+				const firstNonWhitespace = model.getLineFirstNonWhitespaceColumn(selection.endLineNumber);
+				if (selection.endColumn <= firstNonWhitespace) {
+					return new ShiftCommand(selection, {
+						isUnshift: false,
+						tabSize: config.tabSize,
+						indentSize: config.indentSize,
+						insertSpaces: config.insertSpaces,
+						useTabStops: config.useTabStops,
+						autoIndent: config.autoIndent
+					}, config.languageConfigurationService);
+				}
+			}
 			typeText = '\t';
 		}