diff --git a/src/services/smartSelection.ts b/src/services/smartSelection.ts
index 3fcab16695979..6cd5c8f94d854 100644
--- a/src/services/smartSelection.ts
+++ b/src/services/smartSelection.ts
@@ -13,10 +13,16 @@ namespace ts.SmartSelectionRange {
                 const prevNode: Node | undefined = children[i - 1];
                 const node: Node = children[i];
                 const nextNode: Node | undefined = children[i + 1];
+
                 if (getTokenPosOfNode(node, sourceFile, /*includeJsDoc*/ true) > pos) {
                     break outer;
                 }
 
+                const comment = singleOrUndefined(getTrailingCommentRanges(sourceFile.text, node.end));
+                if (comment && comment.kind === SyntaxKind.SingleLineCommentTrivia) {
+                    pushSelectionCommentRange(comment.pos, comment.end);
+                }
+
                 if (positionShouldSnapToNode(sourceFile, pos, node)) {
                     // 1. Blocks are effectively redundant with SyntaxLists.
                     // 2. TemplateSpans, along with the SyntaxLists containing them, are a somewhat unintuitive grouping
@@ -89,6 +95,16 @@ namespace ts.SmartSelectionRange {
                 }
             }
         }
+
+        function pushSelectionCommentRange(start: number, end: number): void {
+            pushSelectionRange(start, end);
+
+            let pos = start;
+            while (sourceFile.text.charCodeAt(pos) === CharacterCodes.slash) {
+                pos++;
+            }
+            pushSelectionRange(pos, end);
+        }
     }
 
     /**
diff --git a/tests/baselines/reference/smartSelection_comment1.baseline b/tests/baselines/reference/smartSelection_comment1.baseline
new file mode 100644
index 0000000000000..2e541c0b2301a
--- /dev/null
+++ b/tests/baselines/reference/smartSelection_comment1.baseline
@@ -0,0 +1,5 @@
+const a = 1; ///**/comment content
+
+               comment content
+             //comment content
+const a = 1; //comment content
\ No newline at end of file
diff --git a/tests/baselines/reference/smartSelection_comment2.baseline b/tests/baselines/reference/smartSelection_comment2.baseline
new file mode 100644
index 0000000000000..ccb5286f0b564
--- /dev/null
+++ b/tests/baselines/reference/smartSelection_comment2.baseline
@@ -0,0 +1,5 @@
+const a = 1; //a b/**/c d
+
+               a bc d
+             //a bc d
+const a = 1; //a bc d
\ No newline at end of file
diff --git a/tests/cases/fourslash/smartSelection_comment1.ts b/tests/cases/fourslash/smartSelection_comment1.ts
new file mode 100644
index 0000000000000..dbd2aa6a16379
--- /dev/null
+++ b/tests/cases/fourslash/smartSelection_comment1.ts
@@ -0,0 +1,5 @@
+/// <reference path="fourslash.ts" />
+
+////const a = 1; ///**/comment content
+
+verify.baselineSmartSelection();
diff --git a/tests/cases/fourslash/smartSelection_comment2.ts b/tests/cases/fourslash/smartSelection_comment2.ts
new file mode 100644
index 0000000000000..1da1b56cf0f80
--- /dev/null
+++ b/tests/cases/fourslash/smartSelection_comment2.ts
@@ -0,0 +1,5 @@
+/// <reference path="fourslash.ts" />
+
+////const a = 1; //a b/**/c d
+
+verify.baselineSmartSelection();