diff --git a/apps/api-extractor/src/collector/Collector.ts b/apps/api-extractor/src/collector/Collector.ts
index f5ca10d6802..6869d70d499 100644
--- a/apps/api-extractor/src/collector/Collector.ts
+++ b/apps/api-extractor/src/collector/Collector.ts
@@ -1,6 +1,8 @@
 // Copyright (c) Microsoft Corporation. All rights reserved. Licensed under the MIT license.
 // See LICENSE in the project root for license information.
 
+import * as path from 'path';
+
 import * as ts from 'typescript';
 import * as tsdoc from '@microsoft/tsdoc';
 import { PackageJsonLookup, Sort, InternalError } from '@rushstack/node-core-library';
@@ -43,6 +45,29 @@ export interface ICollectorOptions {
   extractorConfig: ExtractorConfig;
 }
 
+/**
+ * Resolve the name of a file to an absolute path relative to a TypeScript SourceFile node.
+ */
+function resolveNameRelativeToSourceFile(name: string, source: ts.SourceFile): string {
+  const output: string[] = source.fileName.split(path.sep).slice(0, -1);
+
+  // Process the file name, treating special selectors such as '..' and '.' and '' correctly
+  for (const fragment of name.split('/')) {
+    switch (fragment) {
+      case '..': // parent selector
+        output.pop();
+        break;
+      case '.': // same-dir selectors
+      case '':
+        break;
+      default:
+        output.push(fragment);
+    }
+  }
+
+  return output.join(path.sep);
+}
+
 /**
  * The `Collector` manages the overall data set that is used by `ApiModelGenerator`,
  * `DtsRollupGenerator`, and `ApiReportGenerator`.  Starting from the working package's entry point,
@@ -84,6 +109,7 @@ export class Collector {
 
   private readonly _dtsTypeReferenceDirectives: Set<string> = new Set<string>();
   private readonly _dtsLibReferenceDirectives: Set<string> = new Set<string>();
+  private readonly _dtsFileReferenceDirectives: Set<string> = new Set<string>();
 
   // Used by getOverloadIndex()
   private readonly _cachedOverloadIndexesByDeclaration: Map<AstDeclaration, number>;
@@ -158,6 +184,17 @@ export class Collector {
     return this._dtsLibReferenceDirectives;
   }
 
+  /**
+   * A list of names (e.g. "runtime-library") that should appear in a path-based reference like this:
+   *
+   * ```
+   * /// <reference path="path/to/example.d.ts" />
+   * ```
+   */
+  public get dtsFileReferenceDirectives(): ReadonlySet<string> {
+    return this._dtsFileReferenceDirectives;
+  }
+
   public get entities(): ReadonlyArray<CollectorEntity> {
     return this._entities;
   }
@@ -262,6 +299,7 @@ export class Collector {
     Sort.sortBy(this._entities, (x) => x.getSortKey());
     Sort.sortSet(this._dtsTypeReferenceDirectives);
     Sort.sortSet(this._dtsLibReferenceDirectives);
+    Sort.sortSet(this._dtsFileReferenceDirectives);
     this._starExportedExternalModulePaths.sort();
   }
 
@@ -875,6 +913,11 @@ export class Collector {
             );
             this._dtsLibReferenceDirectives.add(name);
           }
+
+          for (const referencedFile of sourceFile.referencedFiles) {
+            const name: string = sourceFile.text.substring(referencedFile.pos, referencedFile.end);
+            this._dtsFileReferenceDirectives.add(resolveNameRelativeToSourceFile(name, sourceFile));
+          }
         }
       }
     }
diff --git a/apps/api-extractor/src/generators/DtsRollupGenerator.ts b/apps/api-extractor/src/generators/DtsRollupGenerator.ts
index 8c7b46bc2cd..f9e9d399887 100644
--- a/apps/api-extractor/src/generators/DtsRollupGenerator.ts
+++ b/apps/api-extractor/src/generators/DtsRollupGenerator.ts
@@ -3,6 +3,8 @@
 
 /* eslint-disable no-bitwise */
 
+import * as path from 'path';
+
 import * as ts from 'typescript';
 import { FileSystem, NewlineKind, InternalError } from '@rushstack/node-core-library';
 import { ReleaseTag } from '@microsoft/api-extractor-model';
@@ -59,7 +61,7 @@ export class DtsRollupGenerator {
   ): void {
     const stringWriter: StringWriter = new StringWriter();
 
-    DtsRollupGenerator._generateTypingsFileContent(collector, stringWriter, dtsKind);
+    DtsRollupGenerator._generateTypingsFileContent(collector, dtsFilename, stringWriter, dtsKind);
 
     FileSystem.writeFile(dtsFilename, stringWriter.toString(), {
       convertLineEndings: newlineKind,
@@ -69,6 +71,7 @@ export class DtsRollupGenerator {
 
   private static _generateTypingsFileContent(
     collector: Collector,
+    dtsFilename: string,
     stringWriter: StringWriter,
     dtsKind: DtsRollupKind
   ): void {
@@ -87,6 +90,12 @@ export class DtsRollupGenerator {
       stringWriter.writeLine(`/// <reference lib="${libDirectiveReference}" />`);
     }
 
+    for (const fileDirectiveReference of collector.dtsFileReferenceDirectives) {
+      const dtsDirname: string = path.dirname(dtsFilename);
+      const correctedRelativePath: string = path.relative(dtsDirname, fileDirectiveReference);
+      stringWriter.writeLine(`/// <reference path="${correctedRelativePath}" />`);
+    }
+
     // Emit the imports
     for (const entity of collector.entities) {
       if (entity.astEntity instanceof AstImport) {
diff --git a/build-tests/api-extractor-scenarios/config/build-config.json b/build-tests/api-extractor-scenarios/config/build-config.json
index f8ad516b6bd..90d60c83e82 100644
--- a/build-tests/api-extractor-scenarios/config/build-config.json
+++ b/build-tests/api-extractor-scenarios/config/build-config.json
@@ -21,6 +21,7 @@
     "exportStar",
     "exportStar2",
     "exportStar3",
+    "fileReferenceDirectives",
     "functionOverload",
     "importEquals",
     "inconsistentReleaseTags",
diff --git a/build-tests/api-extractor-scenarios/etc/test-outputs/fileReferenceDirectives/api-extractor-scenarios.api.json b/build-tests/api-extractor-scenarios/etc/test-outputs/fileReferenceDirectives/api-extractor-scenarios.api.json
new file mode 100644
index 00000000000..f976fbfe1df
--- /dev/null
+++ b/build-tests/api-extractor-scenarios/etc/test-outputs/fileReferenceDirectives/api-extractor-scenarios.api.json
@@ -0,0 +1,43 @@
+{
+  "metadata": {
+    "toolPackage": "@microsoft/api-extractor",
+    "toolVersion": "[test mode]",
+    "schemaVersion": 1003,
+    "oldestForwardsCompatibleVersion": 1001
+  },
+  "kind": "Package",
+  "canonicalReference": "api-extractor-scenarios!",
+  "docComment": "",
+  "name": "api-extractor-scenarios",
+  "members": [
+    {
+      "kind": "EntryPoint",
+      "canonicalReference": "api-extractor-scenarios!",
+      "name": "",
+      "members": [
+        {
+          "kind": "Variable",
+          "canonicalReference": "api-extractor-scenarios!X:var",
+          "docComment": "/**\n * @public\n */\n",
+          "excerptTokens": [
+            {
+              "kind": "Content",
+              "text": "X: "
+            },
+            {
+              "kind": "Reference",
+              "text": "Foo",
+              "canonicalReference": "!Foo:interface"
+            }
+          ],
+          "releaseTag": "Public",
+          "name": "X",
+          "variableTypeTokenRange": {
+            "startIndex": 1,
+            "endIndex": 2
+          }
+        }
+      ]
+    }
+  ]
+}
diff --git a/build-tests/api-extractor-scenarios/etc/test-outputs/fileReferenceDirectives/api-extractor-scenarios.api.md b/build-tests/api-extractor-scenarios/etc/test-outputs/fileReferenceDirectives/api-extractor-scenarios.api.md
new file mode 100644
index 00000000000..26b1faadd39
--- /dev/null
+++ b/build-tests/api-extractor-scenarios/etc/test-outputs/fileReferenceDirectives/api-extractor-scenarios.api.md
@@ -0,0 +1,13 @@
+## API Report File for "api-extractor-scenarios"
+
+> Do not edit this file. It is a report generated by [API Extractor](https://api-extractor.com/).
+
+```ts
+
+// @public (undocumented)
+export const X: Foo;
+
+
+// (No @packageDocumentation comment for this package)
+
+```
diff --git a/build-tests/api-extractor-scenarios/etc/test-outputs/fileReferenceDirectives/rollup.d.ts b/build-tests/api-extractor-scenarios/etc/test-outputs/fileReferenceDirectives/rollup.d.ts
new file mode 100644
index 00000000000..7fe7b6563c2
--- /dev/null
+++ b/build-tests/api-extractor-scenarios/etc/test-outputs/fileReferenceDirectives/rollup.d.ts
@@ -0,0 +1,8 @@
+/// <reference path="../../../src/fileReferenceDirectives/shim.d.ts" />
+
+/**
+ * @public
+ */
+export declare const X: Foo;
+
+export { }
diff --git a/build-tests/api-extractor-scenarios/src/fileReferenceDirectives/index.ts b/build-tests/api-extractor-scenarios/src/fileReferenceDirectives/index.ts
new file mode 100644
index 00000000000..189b96c55f7
--- /dev/null
+++ b/build-tests/api-extractor-scenarios/src/fileReferenceDirectives/index.ts
@@ -0,0 +1,4 @@
+// Copyright (c) Microsoft Corporation. All rights reserved. Licensed under the MIT license.
+// See LICENSE in the project root for license information.
+
+export { X } from './nested/module';
diff --git a/build-tests/api-extractor-scenarios/src/fileReferenceDirectives/nested/module.ts b/build-tests/api-extractor-scenarios/src/fileReferenceDirectives/nested/module.ts
new file mode 100644
index 00000000000..8297f17196a
--- /dev/null
+++ b/build-tests/api-extractor-scenarios/src/fileReferenceDirectives/nested/module.ts
@@ -0,0 +1,9 @@
+// Copyright (c) Microsoft Corporation. All rights reserved. Licensed under the MIT license.
+// See LICENSE in the project root for license information.
+
+/// <reference path="../shim.d.ts" />
+
+/**
+ * @public
+ */
+export const X: Foo = {};
diff --git a/build-tests/api-extractor-scenarios/src/fileReferenceDirectives/shim.d.ts b/build-tests/api-extractor-scenarios/src/fileReferenceDirectives/shim.d.ts
new file mode 100644
index 00000000000..f0bc540f55d
--- /dev/null
+++ b/build-tests/api-extractor-scenarios/src/fileReferenceDirectives/shim.d.ts
@@ -0,0 +1,4 @@
+// Copyright (c) Microsoft Corporation. All rights reserved. Licensed under the MIT license.
+// See LICENSE in the project root for license information.
+
+declare interface Foo {}