diff --git a/src/cjs-resolve-filename-hook.ts b/src/cjs-resolve-filename-hook.ts
new file mode 100644
index 000000000..9c6f66b02
--- /dev/null
+++ b/src/cjs-resolve-filename-hook.ts
@@ -0,0 +1,59 @@
+import type Module = require('module');
+import type { Service } from '.';
+
+/** @internal */
+export type ModuleConstructorWithInternals = typeof Module & {
+  _resolveFilename(
+    request: string,
+    parent?: Module,
+    isMain?: boolean,
+    options?: ModuleResolveFilenameOptions,
+    ...rest: any[]
+  ): string;
+  _preloadModules(requests?: string[]): void;
+};
+
+interface ModuleResolveFilenameOptions {
+  paths?: Array<string>;
+}
+
+/**
+ * @internal
+ */
+export function installCommonjsResolveHookIfNecessary(tsNodeService: Service) {
+  const Module = require('module') as ModuleConstructorWithInternals;
+  const originalResolveFilename = Module._resolveFilename;
+  const shouldInstallHook = tsNodeService.options.experimentalResolverFeatures;
+  if (shouldInstallHook) {
+    Module._resolveFilename = _resolveFilename;
+  }
+  function _resolveFilename(
+    this: any,
+    request: string,
+    parent?: Module,
+    isMain?: boolean,
+    options?: ModuleResolveFilenameOptions,
+    ...rest: any[]
+  ): string {
+    if (!tsNodeService.enabled())
+      return originalResolveFilename.call(
+        this,
+        request,
+        parent,
+        isMain,
+        options,
+        ...rest
+      );
+
+    // This is a stub to support other pull requests that will be merged in the near future
+    // Right now, it does nothing.
+    return originalResolveFilename.call(
+      this,
+      request,
+      parent,
+      isMain,
+      options,
+      ...rest
+    );
+  }
+}
diff --git a/src/configuration.ts b/src/configuration.ts
index 4ac594155..b536926dd 100644
--- a/src/configuration.ts
+++ b/src/configuration.ts
@@ -277,6 +277,7 @@ function filterRecognizedTsConfigTsNodeOptions(jsonObject: any): {
     moduleTypes,
     experimentalReplAwait,
     swc,
+    experimentalResolverFeatures,
     ...unrecognized
   } = jsonObject as TsConfigOptions;
   const filteredTsConfigOptions = {
@@ -300,6 +301,7 @@ function filterRecognizedTsConfigTsNodeOptions(jsonObject: any): {
     scopeDir,
     moduleTypes,
     swc,
+    experimentalResolverFeatures,
   };
   // Use the typechecker to make sure this implementation has the correct set of properties
   const catchExtraneousProps: keyof TsConfigOptions =
diff --git a/src/index.ts b/src/index.ts
index 613775083..9f85e4bfd 100644
--- a/src/index.ts
+++ b/src/index.ts
@@ -25,6 +25,10 @@ import {
 } from './module-type-classifier';
 import { createResolverFunctions } from './resolver-functions';
 import type { createEsmHooks as createEsmHooksFn } from './esm';
+import {
+  installCommonjsResolveHookIfNecessary,
+  ModuleConstructorWithInternals,
+} from './cjs-resolve-filename-hook';
 
 export { TSCommon };
 export {
@@ -379,6 +383,15 @@ export interface RegisterOptions extends CreateOptions {
    * @default false
    */
   preferTsExts?: boolean;
+
+  /**
+   * Enable experimental features that re-map imports and require calls to support:
+   * `baseUrl`, `paths`, `rootDirs`, `.js` to `.ts` file extension mappings,
+   * `outDir` to `rootDir` mappings for composite projects and monorepos.
+   *
+   * For details, see https://github.com/TypeStrong/ts-node/issues/1514
+   */
+  experimentalResolverFeatures?: boolean;
 }
 
 /**
@@ -546,8 +559,12 @@ export function register(
     originalJsHandler
   );
 
+  installCommonjsResolveHookIfNecessary(service);
+
   // Require specified modules before start-up.
-  (Module as any)._preloadModules(service.options.require);
+  (Module as ModuleConstructorWithInternals)._preloadModules(
+    service.options.require
+  );
 
   return service;
 }
diff --git a/website/docs/options.md b/website/docs/options.md
index 38c9247d9..848b0a75f 100644
--- a/website/docs/options.md
+++ b/website/docs/options.md
@@ -57,6 +57,7 @@ _Environment variables, where available, are in `ALL_CAPS`_
 -  `moduleType`  Override the module type of certain files, ignoring the `package.json` `"type"` field.  See [Module type overrides](./module-type-overrides.md) for details.<br/>*Default:* obeys `package.json` `"type"` and `tsconfig.json` `"module"` <br/>*Can only be specified via `tsconfig.json` or API.*
 - `TS_NODE_HISTORY` Path to history file for REPL <br/>*Default:* `~/.ts_node_repl_history`<br/>
 - `--noExperimentalReplAwait` Disable top-level await in REPL.  Equivalent to node's [`--no-experimental-repl-await`](https://nodejs.org/api/cli.html#cli_no_experimental_repl_await)<br/>*Default:* Enabled if TypeScript version is 3.8 or higher and target is ES2018 or higher.<br/>*Environment:* `TS_NODE_EXPERIMENTAL_REPL_AWAIT` set `false` to disable
+- `experimentalResolverFeatures` Enable experimental features that re-map imports and require calls to support: `baseUrl`, `paths`, `rootDirs`, `.js` to `.ts` file extension mappings, `outDir` to `rootDir` mappings for composite projects and monorepos.  For details, see [#1514](https://github.com/TypeStrong/ts-node/issues/1514)<br/>*Default:* `false`<br/>*Can only be specified via `tsconfig.json` or API.*
 
 ## API