diff --git a/src/harness/fourslashImpl.ts b/src/harness/fourslashImpl.ts
index 3be657d4cd02b..84d4e753ad02f 100644
--- a/src/harness/fourslashImpl.ts
+++ b/src/harness/fourslashImpl.ts
@@ -2500,18 +2500,35 @@ namespace FourSlash {
 
         public printOutliningSpans() {
             const spans = this.languageService.getOutliningSpans(this.activeFile.fileName);
-            Harness.IO.log(`Outlining spans (${spans.length} items)`);
+            Harness.IO.log(`Outlining spans (${spans.length} items)\nResults:`);
             Harness.IO.log(stringify(spans));
+            this.printOutliningSpansInline(spans);
+        }
+
+        private printOutliningSpansInline(spans: ts.OutliningSpan[]) {
+            const allSpanInsets = [] as { text: string, pos: number }[];
+            let annotated = this.activeFile.content;
+            ts.forEach(spans, span => {
+                allSpanInsets.push({ text: "[|", pos: span.textSpan.start });
+                allSpanInsets.push({ text: "|]", pos: span.textSpan.start + span.textSpan.length });
+            });
+
+            const reverseSpans = allSpanInsets.sort((l, r) => r.pos - l.pos);
+            ts.forEach(reverseSpans, span => {
+               annotated = annotated.slice(0, span.pos) + span.text + annotated.slice(span.pos);
+            });
+            Harness.IO.log(`\nMockup:\n${annotated}`);
         }
 
         public verifyOutliningSpans(spans: Range[], kind?: "comment" | "region" | "code" | "imports") {
             const actual = this.languageService.getOutliningSpans(this.activeFile.fileName);
 
-            if (actual.length !== spans.length) {
-                this.raiseError(`verifyOutliningSpans failed - expected total spans to be ${spans.length}, but was ${actual.length}`);
+            const filterActual = ts.filter(actual, f => kind === undefined ? true : f.kind === kind);
+            if (filterActual.length !== spans.length) {
+                this.raiseError(`verifyOutliningSpans failed - expected total spans to be ${spans.length}, but was ${actual.length}\n\nFound Spans:\n\n${this.printOutliningSpansInline(actual)}`);
             }
 
-            ts.zipWith(spans, actual, (expectedSpan, actualSpan, i) => {
+            ts.zipWith(spans, filterActual, (expectedSpan, actualSpan, i) => {
                 if (expectedSpan.pos !== actualSpan.textSpan.start || expectedSpan.end !== ts.textSpanEnd(actualSpan.textSpan)) {
                     return this.raiseError(`verifyOutliningSpans failed - span ${(i + 1)} expected: (${expectedSpan.pos},${expectedSpan.end}),  actual: (${actualSpan.textSpan.start},${ts.textSpanEnd(actualSpan.textSpan)})`);
                 }
diff --git a/src/services/outliningElementsCollector.ts b/src/services/outliningElementsCollector.ts
index b6212e2a2d285..ab8cfb3f6c33e 100644
--- a/src/services/outliningElementsCollector.ts
+++ b/src/services/outliningElementsCollector.ts
@@ -10,7 +10,8 @@ namespace ts.OutliningElementsCollector {
     function addNodeOutliningSpans(sourceFile: SourceFile, cancellationToken: CancellationToken, out: Push<OutliningSpan>): void {
         let depthRemaining = 40;
         let current = 0;
-        const statements = sourceFile.statements;
+        // Includes the EOF Token so that comments which aren't attached to statements are included
+        const statements = [...sourceFile.statements, sourceFile.endOfFileToken];
         const n = statements.length;
         while (current < n) {
             while (current < n && !isAnyImportSyntax(statements[current])) {
@@ -33,7 +34,7 @@ namespace ts.OutliningElementsCollector {
             if (depthRemaining === 0) return;
             cancellationToken.throwIfCancellationRequested();
 
-            if (isDeclaration(n)) {
+            if (isDeclaration(n) || n.kind === SyntaxKind.EndOfFileToken) {
                 addOutliningForLeadingCommentsForNode(n, sourceFile, cancellationToken, out);
             }
 
diff --git a/tests/cases/fourslash/fourslash.ts b/tests/cases/fourslash/fourslash.ts
index d44148972fbf9..beb9d0c4d841f 100644
--- a/tests/cases/fourslash/fourslash.ts
+++ b/tests/cases/fourslash/fourslash.ts
@@ -317,7 +317,7 @@ declare namespace FourSlashInterface {
         baselineQuickInfo(): void;
         baselineSmartSelection(): void;
         nameOrDottedNameSpanTextIs(text: string): void;
-        outliningSpansInCurrentFile(spans: Range[]): void;
+        outliningSpansInCurrentFile(spans: Range[], kind?: "comment" | "region" | "code" | "imports"): void;
         outliningHintSpansInCurrentFile(spans: Range[]): void;
         todoCommentsInCurrentFile(descriptors: string[]): void;
         matchingBracePositionInCurrentFile(bracePosition: number, expectedMatchPosition: number): void;
diff --git a/tests/cases/fourslash/outlineSpansBlockCommentsWithoutStatements.ts b/tests/cases/fourslash/outlineSpansBlockCommentsWithoutStatements.ts
new file mode 100644
index 0000000000000..1d0fd91e78327
--- /dev/null
+++ b/tests/cases/fourslash/outlineSpansBlockCommentsWithoutStatements.ts
@@ -0,0 +1,9 @@
+/// <reference path="fourslash.ts"/>
+
+// #22732
+
+////[|/*
+///// * Some text
+////  */|]
+
+verify.outliningHintSpansInCurrentFile(test.ranges());
diff --git a/tests/cases/fourslash/outlineSpansTrailingBlockCommentsAfterStatements.ts b/tests/cases/fourslash/outlineSpansTrailingBlockCommentsAfterStatements.ts
new file mode 100644
index 0000000000000..2397be94b56f1
--- /dev/null
+++ b/tests/cases/fourslash/outlineSpansTrailingBlockCommentsAfterStatements.ts
@@ -0,0 +1,10 @@
+/// <reference path="fourslash.ts"/>
+
+// #22732
+
+////console.log(0);
+////[|/*
+///// * Some text
+////  */|]
+
+verify.outliningHintSpansInCurrentFile(test.ranges());
diff --git a/tests/cases/fourslash/server/getOutliningSpansForRegions.ts b/tests/cases/fourslash/server/getOutliningSpansForRegions.ts
index 81d2409cf9db7..dbfe68204dc75 100644
--- a/tests/cases/fourslash/server/getOutliningSpansForRegions.ts
+++ b/tests/cases/fourslash/server/getOutliningSpansForRegions.ts
@@ -48,4 +48,4 @@
 ////// #endregion
 ////*/
 
-verify.outliningSpansInCurrentFile(test.ranges(), "region");
+verify.outliningSpansInCurrentFile(test.ranges(), "region");
\ No newline at end of file