diff --git a/src/compiler/parser.ts b/src/compiler/parser.ts
index 80bea252a5e..ed200683849 100644
--- a/src/compiler/parser.ts
+++ b/src/compiler/parser.ts
@@ -1555,7 +1555,10 @@ namespace ts {
             return false;
         }
 
-        function parseExpectedMatchingBrackets(openKind: SyntaxKind, closeKind: SyntaxKind, openPosition: number) {
+        function parseExpectedMatchingBrackets(openKind: SyntaxKind, closeKind: SyntaxKind,  openParsed: boolean, openPosition: number) {
+            if (!openParsed) {
+                return parseExpected(closeKind);
+            }
             if (token() === closeKind) {
                 nextToken();
                 return;
@@ -5499,10 +5502,10 @@ namespace ts {
         function parseArrayLiteralExpression(): ArrayLiteralExpression {
             const pos = getNodePos();
             const openBracketPosition = scanner.getTokenPos();
-            parseExpected(SyntaxKind.OpenBracketToken);
+            const openBracketParsed = parseExpected(SyntaxKind.OpenBracketToken);
             const multiLine = scanner.hasPrecedingLineBreak();
             const elements = parseDelimitedList(ParsingContext.ArrayLiteralMembers, parseArgumentOrArrayLiteralElement);
-            parseExpectedMatchingBrackets(SyntaxKind.OpenBracketToken, SyntaxKind.CloseBracketToken, openBracketPosition);
+            parseExpectedMatchingBrackets(SyntaxKind.OpenBracketToken, SyntaxKind.CloseBracketToken, openBracketParsed, openBracketPosition);
             return finishNode(factory.createArrayLiteralExpression(elements, multiLine), pos);
         }
 
@@ -5568,10 +5571,10 @@ namespace ts {
         function parseObjectLiteralExpression(): ObjectLiteralExpression {
             const pos = getNodePos();
             const openBracePosition = scanner.getTokenPos();
-            parseExpected(SyntaxKind.OpenBraceToken);
+            const openBraceParsed = parseExpected(SyntaxKind.OpenBraceToken);
             const multiLine = scanner.hasPrecedingLineBreak();
             const properties = parseDelimitedList(ParsingContext.ObjectLiteralMembers, parseObjectLiteralElement, /*considerSemicolonAsDelimiter*/ true);
-            parseExpectedMatchingBrackets(SyntaxKind.OpenBraceToken, SyntaxKind.CloseBraceToken, openBracePosition);
+            parseExpectedMatchingBrackets(SyntaxKind.OpenBraceToken, SyntaxKind.CloseBraceToken, openBraceParsed, openBracePosition);
             return finishNode(factory.createObjectLiteralExpression(properties, multiLine), pos);
         }
 
@@ -5654,10 +5657,11 @@ namespace ts {
             const pos = getNodePos();
             const hasJSDoc = hasPrecedingJSDocComment();
             const openBracePosition = scanner.getTokenPos();
-            if (parseExpected(SyntaxKind.OpenBraceToken, diagnosticMessage) || ignoreMissingOpenBrace) {
+            const openBraceParsed = parseExpected(SyntaxKind.OpenBraceToken, diagnosticMessage)
+            if (openBraceParsed || ignoreMissingOpenBrace) {
                 const multiLine = scanner.hasPrecedingLineBreak();
                 const statements = parseList(ParsingContext.BlockStatements, parseStatement);
-                parseExpectedMatchingBrackets(SyntaxKind.OpenBraceToken, SyntaxKind.CloseBraceToken, openBracePosition);
+                parseExpectedMatchingBrackets(SyntaxKind.OpenBraceToken, SyntaxKind.CloseBraceToken, openBraceParsed, openBracePosition);
                 const result = withJSDoc(finishNode(factory.createBlock(statements, multiLine), pos), hasJSDoc);
                 if (token() === SyntaxKind.EqualsToken) {
                     parseErrorAtCurrentToken(Diagnostics.Declaration_or_statement_expected_This_follows_a_block_of_statements_so_if_you_intended_to_write_a_destructuring_assignment_you_might_need_to_wrap_the_the_whole_assignment_in_parentheses);
@@ -5714,9 +5718,9 @@ namespace ts {
             const hasJSDoc = hasPrecedingJSDocComment();
             parseExpected(SyntaxKind.IfKeyword);
             const openParenPosition = scanner.getTokenPos();
-            parseExpected(SyntaxKind.OpenParenToken);
+            const openParenParsed = parseExpected(SyntaxKind.OpenParenToken);
             const expression = allowInAnd(parseExpression);
-            parseExpectedMatchingBrackets(SyntaxKind.OpenParenToken, SyntaxKind.CloseParenToken, openParenPosition);
+            parseExpectedMatchingBrackets(SyntaxKind.OpenParenToken, SyntaxKind.CloseParenToken, openParenParsed, openParenPosition)
             const thenStatement = parseStatement();
             const elseStatement = parseOptional(SyntaxKind.ElseKeyword) ? parseStatement() : undefined;
             return withJSDoc(finishNode(factory.createIfStatement(expression, thenStatement, elseStatement), pos), hasJSDoc);
@@ -5729,9 +5733,9 @@ namespace ts {
             const statement = parseStatement();
             parseExpected(SyntaxKind.WhileKeyword);
             const openParenPosition = scanner.getTokenPos();
-            parseExpected(SyntaxKind.OpenParenToken);
+            const openParenParsed = parseExpected(SyntaxKind.OpenParenToken);
             const expression = allowInAnd(parseExpression);
-            parseExpectedMatchingBrackets(SyntaxKind.OpenParenToken, SyntaxKind.CloseParenToken, openParenPosition);
+            parseExpectedMatchingBrackets(SyntaxKind.OpenParenToken, SyntaxKind.CloseParenToken, openParenParsed, openParenPosition)
 
             // From: https://mail.mozilla.org/pipermail/es-discuss/2011-August/016188.html
             // 157 min --- All allen at wirfs-brock.com CONF --- "do{;}while(false)false" prohibited in
@@ -5746,9 +5750,9 @@ namespace ts {
             const hasJSDoc = hasPrecedingJSDocComment();
             parseExpected(SyntaxKind.WhileKeyword);
             const openParenPosition = scanner.getTokenPos();
-            parseExpected(SyntaxKind.OpenParenToken);
+            const openParenParsed = parseExpected(SyntaxKind.OpenParenToken);
             const expression = allowInAnd(parseExpression);
-            parseExpectedMatchingBrackets(SyntaxKind.OpenParenToken, SyntaxKind.CloseParenToken, openParenPosition);
+            parseExpectedMatchingBrackets(SyntaxKind.OpenParenToken, SyntaxKind.CloseParenToken, openParenParsed, openParenPosition);
             const statement = parseStatement();
             return withJSDoc(finishNode(factory.createWhileStatement(expression, statement), pos), hasJSDoc);
         }
@@ -5825,9 +5829,9 @@ namespace ts {
             const hasJSDoc = hasPrecedingJSDocComment();
             parseExpected(SyntaxKind.WithKeyword);
             const openParenPosition = scanner.getTokenPos();
-            parseExpected(SyntaxKind.OpenParenToken);
+            const openParenParsed = parseExpected(SyntaxKind.OpenParenToken);
             const expression = allowInAnd(parseExpression);
-            parseExpectedMatchingBrackets(SyntaxKind.OpenParenToken, SyntaxKind.CloseParenToken, openParenPosition);
+            parseExpectedMatchingBrackets(SyntaxKind.OpenParenToken, SyntaxKind.CloseParenToken, openParenParsed, openParenPosition);
             const statement = doInsideOfContext(NodeFlags.InWithStatement, parseStatement);
             return withJSDoc(finishNode(factory.createWithStatement(expression, statement), pos), hasJSDoc);
         }
diff --git a/tests/baselines/reference/reservedWords2.errors.txt b/tests/baselines/reference/reservedWords2.errors.txt
index 6ecb9471631..599010b4368 100644
--- a/tests/baselines/reference/reservedWords2.errors.txt
+++ b/tests/baselines/reference/reservedWords2.errors.txt
@@ -45,7 +45,6 @@ tests/cases/compiler/reservedWords2.ts(12,17): error TS1138: Parameter declarati
 !!! error TS2580: Cannot find name 'require'. Do you need to install type definitions for node? Try `npm i --save-dev @types/node`.
                                   ~
 !!! error TS1005: ')' expected.
-!!! related TS1007 tests/cases/compiler/reservedWords2.ts:1:14: The parser expected to find a ')' to match the '(' token here.
     import * as  while from "foo"
                
 !!! error TS2300: Duplicate identifier '(Missing)'.
@@ -59,7 +58,6 @@ tests/cases/compiler/reservedWords2.ts(12,17): error TS1138: Parameter declarati
 !!! error TS2304: Cannot find name 'from'.
                             ~~~~~
 !!! error TS1005: ')' expected.
-!!! related TS1007 tests/cases/compiler/reservedWords2.ts:2:20: The parser expected to find a ')' to match the '(' token here.
     
     var typeof = 10;
         ~~~~~~
diff --git a/tests/cases/fourslash/smartIndentMissingBracketsDoKeyword.ts b/tests/cases/fourslash/smartIndentMissingBracketsDoKeyword.ts
new file mode 100644
index 00000000000..984499db5ae
--- /dev/null
+++ b/tests/cases/fourslash/smartIndentMissingBracketsDoKeyword.ts
@@ -0,0 +1,7 @@
+/// <reference path='fourslash.ts'/>
+
+////do {/*1*/
+
+goTo.marker("1");
+edit.insert("\n");
+verify.indentationIs(4);
diff --git a/tests/cases/fourslash/smartIndentMissingBracketsIfKeyword.ts b/tests/cases/fourslash/smartIndentMissingBracketsIfKeyword.ts
new file mode 100644
index 00000000000..0e260cdf142
--- /dev/null
+++ b/tests/cases/fourslash/smartIndentMissingBracketsIfKeyword.ts
@@ -0,0 +1,7 @@
+/// <reference path='fourslash.ts'/>
+
+////if /*1*/
+
+goTo.marker("1");
+edit.insert("\n");
+verify.indentationIs(4);
diff --git a/tests/cases/fourslash/smartIndentMissingBracketsWhileKeyword.ts b/tests/cases/fourslash/smartIndentMissingBracketsWhileKeyword.ts
new file mode 100644
index 00000000000..03e9be630ca
--- /dev/null
+++ b/tests/cases/fourslash/smartIndentMissingBracketsWhileKeyword.ts
@@ -0,0 +1,7 @@
+/// <reference path='fourslash.ts'/>
+
+////while /*1*/
+
+goTo.marker("1");
+edit.insert("\n");
+verify.indentationIs(4);
diff --git a/tests/cases/fourslash/smartIndentMissingBracketsWithKeyword.ts b/tests/cases/fourslash/smartIndentMissingBracketsWithKeyword.ts
new file mode 100644
index 00000000000..733fc0560a7
--- /dev/null
+++ b/tests/cases/fourslash/smartIndentMissingBracketsWithKeyword.ts
@@ -0,0 +1,7 @@
+/// <reference path='fourslash.ts'/>
+
+////with /*1*/
+
+goTo.marker("1");
+edit.insert("\n");
+verify.indentationIs(0);