diff --git a/src/services/outliningElementsCollector.ts b/src/services/outliningElementsCollector.ts
index 5099f8b66bdd5..e0d99d1d27165 100644
--- a/src/services/outliningElementsCollector.ts
+++ b/src/services/outliningElementsCollector.ts
@@ -1,13 +1,20 @@
 /* @internal */
 namespace ts.OutliningElementsCollector {
+    const collapseText = "...";
+    const maxDepth = 20;
+
     export function collectElements(sourceFile: SourceFile, cancellationToken: CancellationToken): OutliningSpan[] {
         const elements: OutliningSpan[] = [];
-        const collapseText = "...";
+        let depth = 0;
 
-        function addOutliningSpan(hintSpanNode: Node, startElement: Node, endElement: Node, autoCollapse: boolean) {
+        walk(sourceFile);
+        return elements;
+
+        /** If useFullStart is true, then the collapsing span includes leading whitespace, including linebreaks. */
+        function addOutliningSpan(hintSpanNode: Node, startElement: Node, endElement: Node, autoCollapse: boolean, useFullStart: boolean) {
             if (hintSpanNode && startElement && endElement) {
                 const span: OutliningSpan = {
-                    textSpan: createTextSpanFromBounds(startElement.pos, endElement.end),
+                    textSpan: createTextSpanFromBounds(useFullStart ? startElement.getFullStart() : startElement.getStart(), endElement.getEnd()),
                     hintSpan: createTextSpanFromNode(hintSpanNode, sourceFile),
                     bannerText: collapseText,
                     autoCollapse,
@@ -82,8 +89,6 @@ namespace ts.OutliningElementsCollector {
             return isFunctionBlock(node) && node.parent.kind !== SyntaxKind.ArrowFunction;
         }
 
-        let depth = 0;
-        const maxDepth = 20;
         function walk(n: Node): void {
             cancellationToken.throwIfCancellationRequested();
             if (depth > maxDepth) {
@@ -113,7 +118,7 @@ namespace ts.OutliningElementsCollector {
                             parent.kind === SyntaxKind.WithStatement ||
                             parent.kind === SyntaxKind.CatchClause) {
 
-                            addOutliningSpan(parent, openBrace, closeBrace, autoCollapse(n));
+                            addOutliningSpan(parent, openBrace, closeBrace, autoCollapse(n), /*useFullStart*/ true);
                             break;
                         }
 
@@ -121,13 +126,13 @@ namespace ts.OutliningElementsCollector {
                             // Could be the try-block, or the finally-block.
                             const tryStatement = <TryStatement>parent;
                             if (tryStatement.tryBlock === n) {
-                                addOutliningSpan(parent, openBrace, closeBrace, autoCollapse(n));
+                                addOutliningSpan(parent, openBrace, closeBrace, autoCollapse(n), /*useFullStart*/ true);
                                 break;
                             }
                             else if (tryStatement.finallyBlock === n) {
                                 const finallyKeyword = findChildOfKind(tryStatement, SyntaxKind.FinallyKeyword, sourceFile);
                                 if (finallyKeyword) {
-                                    addOutliningSpan(finallyKeyword, openBrace, closeBrace, autoCollapse(n));
+                                    addOutliningSpan(finallyKeyword, openBrace, closeBrace, autoCollapse(n), /*useFullStart*/ true);
                                     break;
                                 }
                             }
@@ -151,31 +156,35 @@ namespace ts.OutliningElementsCollector {
                 case SyntaxKind.ModuleBlock: {
                     const openBrace = findChildOfKind(n, SyntaxKind.OpenBraceToken, sourceFile);
                     const closeBrace = findChildOfKind(n, SyntaxKind.CloseBraceToken, sourceFile);
-                    addOutliningSpan(n.parent, openBrace, closeBrace, autoCollapse(n));
+                    addOutliningSpan(n.parent, openBrace, closeBrace, autoCollapse(n), /*useFullStart*/ true);
                     break;
                 }
                 case SyntaxKind.ClassDeclaration:
                 case SyntaxKind.InterfaceDeclaration:
                 case SyntaxKind.EnumDeclaration:
-                case SyntaxKind.ObjectLiteralExpression:
                 case SyntaxKind.CaseBlock: {
                     const openBrace = findChildOfKind(n, SyntaxKind.OpenBraceToken, sourceFile);
                     const closeBrace = findChildOfKind(n, SyntaxKind.CloseBraceToken, sourceFile);
-                    addOutliningSpan(n, openBrace, closeBrace, autoCollapse(n));
+                    addOutliningSpan(n, openBrace, closeBrace, autoCollapse(n), /*useFullStart*/ true);
                     break;
                 }
+                // If the block has no leading keywords and is inside an array literal,
+                // we only want to collapse the span of the block.
+                // Otherwise, the collapsed section will include the end of the previous line.
+                case SyntaxKind.ObjectLiteralExpression:
+                    const openBrace = findChildOfKind(n, SyntaxKind.OpenBraceToken, sourceFile);
+                    const closeBrace = findChildOfKind(n, SyntaxKind.CloseBraceToken, sourceFile);
+                    addOutliningSpan(n, openBrace, closeBrace, autoCollapse(n), /*useFullStart*/ !isArrayLiteralExpression(n.parent));
+                    break;
                 case SyntaxKind.ArrayLiteralExpression:
                     const openBracket = findChildOfKind(n, SyntaxKind.OpenBracketToken, sourceFile);
                     const closeBracket = findChildOfKind(n, SyntaxKind.CloseBracketToken, sourceFile);
-                    addOutliningSpan(n, openBracket, closeBracket, autoCollapse(n));
+                    addOutliningSpan(n, openBracket, closeBracket, autoCollapse(n), /*useFullStart*/ !isArrayLiteralExpression(n.parent));
                     break;
             }
             depth++;
             forEachChild(n, walk);
             depth--;
         }
-
-        walk(sourceFile);
-        return elements;
     }
 }
\ No newline at end of file
diff --git a/tests/cases/fourslash/getOutliningForObjectsInArray.ts b/tests/cases/fourslash/getOutliningForObjectsInArray.ts
new file mode 100644
index 0000000000000..896342248328a
--- /dev/null
+++ b/tests/cases/fourslash/getOutliningForObjectsInArray.ts
@@ -0,0 +1,56 @@
+/// <reference path="fourslash.ts"/>
+
+// objects in x should generate outlining spans that do not render in VS
+//// const x =[| [
+////     [|{ a: 0 }|],
+////     [|{ b: 1 }|],
+////     [|{ c: 2 }|]
+//// ]|];
+////
+// objects in y should generate outlining spans that render as expected
+//// const y =[| [
+////     [|{
+////         a: 0
+////     }|],
+////     [|{
+////         b: 1
+////     }|],
+////     [|{
+////         c: 2
+////     }|]
+//// ]|];
+////
+// same behavior for nested arrays
+//// const w =[| [
+////     [|[ 0 ]|],
+////     [|[ 1 ]|],
+////     [|[ 2 ]|]
+//// ]|];
+////
+//// const z =[| [
+////     [|[
+////         0
+////     ]|],
+////     [|[
+////         1
+////     ]|],
+////     [|[
+////         2
+////     ]|]
+//// ]|];
+////
+// multiple levels of nesting work as expected
+//// const z =[| [
+////     [|[
+////         [|{ hello: 0 }|]
+////     ]|],
+////     [|[
+////         [|{ hello: 3 }|]
+////     ]|],
+////     [|[
+////         [|{ hello: 5 }|],
+////         [|{ hello: 7 }|]
+////     ]|]
+//// ]|];
+
+verify.outliningSpansInCurrentFile(test.ranges());
\ No newline at end of file