diff --git a/src/services/services.ts b/src/services/services.ts
index 36638f78671..983439f27c7 100644
--- a/src/services/services.ts
+++ b/src/services/services.ts
@@ -2068,6 +2068,7 @@ namespace ts {
             const textChanges: TextChange[] = [];
             const { text } = sourceFile;
 
+            let hasComment = false;
             let isCommenting = insertComment || false;
             const positions = [] as number[] as SortedArray<number>;
 
@@ -2098,6 +2099,7 @@ namespace ts {
                         positions.push(commentRange.end);
                     }
 
+                    hasComment = true;
                     pos = commentRange.end + 1;
                 }
                 else { // If it's not in a comment range, then we need to comment the uncommented portions.
@@ -2110,7 +2112,9 @@ namespace ts {
                 }
             }
 
-            if (isCommenting) {
+            // If it didn't found a comment and isCommenting is false means is only empty space.
+            // We want to insert comment in this scenario.
+            if (isCommenting || !hasComment) {
                 if (isInComment(sourceFile, textRange.pos)?.kind !== SyntaxKind.SingleLineCommentTrivia) {
                     insertSorted(positions, textRange.pos, compareValues);
                 }
diff --git a/src/services/utilities.ts b/src/services/utilities.ts
index 18bdf9557fd..29c09102424 100644
--- a/src/services/utilities.ts
+++ b/src/services/utilities.ts
@@ -1321,7 +1321,7 @@ namespace ts {
     }
 
     export function isInsideJsxElement(sourceFile: SourceFile, position: number): boolean {
-        function isInsideJsxElementRecursion(node: Node): boolean {
+        function isInsideJsxElementTraversal(node: Node): boolean {
             while (node) {
                 if (node.kind >= SyntaxKind.JsxSelfClosingElement && node.kind <= SyntaxKind.JsxExpression
                     || node.kind === SyntaxKind.JsxText
@@ -1334,7 +1334,9 @@ namespace ts {
                     node = node.parent;
                 }
                 else if (node.kind === SyntaxKind.JsxElement) {
-                    return position > node.getStart(sourceFile) || isInsideJsxElementRecursion(node.parent);
+                    if (position > node.getStart(sourceFile)) return true;
+
+                    node = node.parent;
                 }
                 else {
                     return false;
@@ -1344,7 +1346,7 @@ namespace ts {
             return false;
         }
 
-        return isInsideJsxElementRecursion(getTokenAtPosition(sourceFile, position));
+        return isInsideJsxElementTraversal(getTokenAtPosition(sourceFile, position));
     }
 
     export function findPrecedingMatchingToken(token: Node, matchingTokenKind: SyntaxKind, sourceFile: SourceFile) {
@@ -2279,8 +2281,8 @@ namespace ts {
             // This only happens for leaf nodes - internal nodes always see their children change.
             const clone =
                 isStringLiteral(node) ? setOriginalNode(factory.createStringLiteralFromNode(node), node) as Node as T :
-                isNumericLiteral(node) ? setOriginalNode(factory.createNumericLiteral(node.text, node.numericLiteralFlags), node) as Node as T :
-                factory.cloneNode(node);
+                    isNumericLiteral(node) ? setOriginalNode(factory.createNumericLiteral(node.text, node.numericLiteralFlags), node) as Node as T :
+                        factory.cloneNode(node);
             return setTextRange(clone, node);
         }
 
diff --git a/tests/cases/fourslash/toggleMultilineComment1.ts b/tests/cases/fourslash/toggleMultilineComment1.ts
index d32e7b28ecf..f76e9d56473 100644
--- a/tests/cases/fourslash/toggleMultilineComment1.ts
+++ b/tests/cases/fourslash/toggleMultilineComment1.ts
@@ -11,6 +11,8 @@
 //// [|/*let var7 = 1;
 //// let var8 = 2;
 //// let var9 = 3;*/|]
+//// 
+//// let var10[||] = 10;
 
 verify.toggleMultilineComment(
     `let var1/* = 1;
@@ -23,4 +25,6 @@ let var6 = 3;
 
 let var7 = 1;
 let var8 = 2;
-let var9 = 3;`);
\ No newline at end of file
+let var9 = 3;
+
+let var10/**/ = 10;`);
\ No newline at end of file
diff --git a/tests/cases/fourslash/toggleMultilineComment9.ts b/tests/cases/fourslash/toggleMultilineComment9.ts
new file mode 100644
index 00000000000..f9761a98773
--- /dev/null
+++ b/tests/cases/fourslash/toggleMultilineComment9.ts
@@ -0,0 +1,30 @@
+// When there's is only whitespace, insert comment. If there is whitespace but theres a comment in bewteen, then uncomment.
+
+//// /*let var1[| = 1;*/
+////     |]
+//// 
+//// [|    
+//// /*let var2 = 2;*/|]
+//// 
+//// [|
+//// 
+//// |]
+//// 
+////     [||]
+//// 
+//// let var3[||] = 3;
+
+verify.toggleMultilineComment(
+    `let var1 = 1;
+    
+
+    
+let var2 = 2;
+
+/*
+
+*/
+
+    /**/
+
+let var3/**/ = 3;`);
\ No newline at end of file
diff --git a/tests/cases/fourslash/uncommentSelection1.ts b/tests/cases/fourslash/uncommentSelection1.ts
index 77066e49152..2245cbc2d00 100644
--- a/tests/cases/fourslash/uncommentSelection1.ts
+++ b/tests/cases/fourslash/uncommentSelection1.ts
@@ -17,6 +17,8 @@
 //// let var11[||]/* = 1;
 //// let var12 = 2;
 //// let var13 */= 3;
+//// 
+//// ////let var14 [||]= 14;
 
 verify.uncommentSelection(
     `let var1 = 1;
@@ -35,4 +37,6 @@ let var10 = 3;
 
 let var11 = 1;
 let var12 = 2;
-let var13 = 3;`);
\ No newline at end of file
+let var13 = 3;
+
+//let var14 = 14;`);
\ No newline at end of file