diff --git a/src/services/textChanges.ts b/src/services/textChanges.ts
index 41f0797ca8ef9..131cb029c6537 100644
--- a/src/services/textChanges.ts
+++ b/src/services/textChanges.ts
@@ -384,7 +384,7 @@ namespace ts.textChanges {
             }
         }
 
-        public insertNodeBefore(sourceFile: SourceFile, before: Node, newNode: Node, blankLineBetween = false, options = {}): void {
+        public insertNodeBefore(sourceFile: SourceFile, before: Node, newNode: Node, blankLineBetween = false, options: ConfigurableStartEnd = {}): void {
             this.insertNodeAt(sourceFile, getAdjustedStartPosition(sourceFile, before, options), newNode, this.getOptionsForInsertNodeBefore(before, newNode, blankLineBetween));
         }
 
diff --git a/src/services/utilities.ts b/src/services/utilities.ts
index 216586c8f86ad..a0ab840cf07b1 100644
--- a/src/services/utilities.ts
+++ b/src/services/utilities.ts
@@ -1913,9 +1913,10 @@ namespace ts {
             for (const newImport of sortedNewImports) {
                 const insertionIndex = OrganizeImports.getImportDeclarationInsertionIndex(existingImportStatements, newImport);
                 if (insertionIndex === 0) {
-                    changes.insertNodeBefore(sourceFile, existingImportStatements[0], newImport, /*blankLineBetween*/ false, {
-                        leadingTriviaOption: textChanges.LeadingTriviaOption.Exclude,
-                    });
+                    // If the first import is top-of-file, insert after the leading comment which is likely the header.
+                    const options = existingImportStatements[0] === sourceFile.statements[0] ?
+                    { leadingTriviaOption: textChanges.LeadingTriviaOption.Exclude } : {};
+                    changes.insertNodeBefore(sourceFile, existingImportStatements[0], newImport, /*blankLineBetween*/ false, options);
                 }
                 else {
                     const prevImport = existingImportStatements[insertionIndex - 1];
diff --git a/tests/cases/fourslash/importNameCodeFix_HeaderComment.ts b/tests/cases/fourslash/importNameCodeFix_HeaderComment1.ts
similarity index 100%
rename from tests/cases/fourslash/importNameCodeFix_HeaderComment.ts
rename to tests/cases/fourslash/importNameCodeFix_HeaderComment1.ts
diff --git a/tests/cases/fourslash/importNameCodeFix_HeaderComment2.ts b/tests/cases/fourslash/importNameCodeFix_HeaderComment2.ts
new file mode 100644
index 0000000000000..994d770ff24c5
--- /dev/null
+++ b/tests/cases/fourslash/importNameCodeFix_HeaderComment2.ts
@@ -0,0 +1,32 @@
+/// <reference path="fourslash.ts" />
+
+// @Filename: /a.ts
+////export const foo = 0;
+
+// @Filename: /b.ts
+////export const bar = 0;
+
+// @Filename: /c.ts
+/////*--------------------
+//// *  Copyright Header
+//// *--------------------*/
+////
+////const afterHeader = 1;
+////
+////// non-header comment
+////import { bar } from "./b";
+////foo;
+
+goTo.file("/c.ts");
+verify.importFixAtPosition([
+`/*--------------------
+ *  Copyright Header
+ *--------------------*/
+
+const afterHeader = 1;
+
+import { foo } from "./a";
+// non-header comment
+import { bar } from "./b";
+foo;`,
+]);