diff --git a/api-extractor/ts-node.api.md b/api-extractor/ts-node.api.md
index 6d42f4a42..1d7ad1289 100644
--- a/api-extractor/ts-node.api.md
+++ b/api-extractor/ts-node.api.md
@@ -28,6 +28,7 @@ export interface CreateOptions {
     emit?: boolean;
     esm?: boolean;
     experimentalReplAwait?: boolean;
+    preprocessor?: string;
     experimentalSpecifierResolution?: 'node' | 'explicit';
     experimentalTsImportSpecifiers?: boolean;
     // (undocumented)
diff --git a/package.json b/package.json
index 8f3f4464e..b17064872 100644
--- a/package.json
+++ b/package.json
@@ -162,6 +162,7 @@
     "arg": "^4.1.0",
     "diff": "^4.0.1",
     "make-error": "^1.1.1",
+    "pretty-repl": "^3.1.1",
     "v8-compile-cache-lib": "^3.0.1"
   },
   "prettier": {
diff --git a/src/bin.ts b/src/bin.ts
index 542fb6841..4911d3497 100644
--- a/src/bin.ts
+++ b/src/bin.ts
@@ -140,6 +140,7 @@ function parseArgv(argv: string[], entrypointArgs: Record<string, any>) {
         '--scope': Boolean,
         '--scopeDir': String,
         '--noExperimentalReplAwait': Boolean,
+        '--preprocessor': String,
         '--experimentalSpecifierResolution': String,
 
         // Aliases.
@@ -218,6 +219,7 @@ function parseArgv(argv: string[], entrypointArgs: Record<string, any>) {
     '--scope': scope = undefined,
     '--scopeDir': scopeDir = undefined,
     '--noExperimentalReplAwait': noExperimentalReplAwait,
+    '--preprocessor': preprocessor,
     '--experimentalSpecifierResolution': experimentalSpecifierResolution,
     '--esm': esm,
     _: restArgs,
@@ -257,6 +259,7 @@ function parseArgv(argv: string[], entrypointArgs: Record<string, any>) {
     scope,
     scopeDir,
     noExperimentalReplAwait,
+    preprocessor,
     experimentalSpecifierResolution,
     esm,
   };
@@ -278,6 +281,7 @@ Options:
 
   --esm                           Bootstrap with the ESM loader, enabling full ESM support
   --swc                           Use the faster swc transpiler
+  --preprocessor                  Runs at the start of CLI
 
   -h, --help                      Print CLI usage
   -v, --version                   Print module version information.  -vvv to print additional information
@@ -355,6 +359,7 @@ function phase3(payload: BootstrapState) {
     scopeDir,
     esm,
     experimentalSpecifierResolution,
+    preprocessor,
   } = payload.parseArgvResult;
   const { cwd } = payload.phase2Result!;
 
@@ -398,6 +403,7 @@ function phase3(payload: BootstrapState) {
     esm,
     experimentalSpecifierResolution:
       experimentalSpecifierResolution as ExperimentalSpecifierResolution,
+    preprocessor,
   });
 
   // If ESM is enabled through the parsed tsconfig, stage4 should be run in a child
diff --git a/src/configuration.ts b/src/configuration.ts
index c59536986..0dd4f6c8a 100644
--- a/src/configuration.ts
+++ b/src/configuration.ts
@@ -401,6 +401,7 @@ function filterRecognizedTsConfigTsNodeOptions(jsonObject: any): {
     scopeDir,
     moduleTypes,
     experimentalReplAwait,
+    preprocessor,
     swc,
     experimentalResolver,
     esm,
@@ -414,6 +415,7 @@ function filterRecognizedTsConfigTsNodeOptions(jsonObject: any): {
     compilerOptions,
     emit,
     experimentalReplAwait,
+    preprocessor,
     files,
     ignore,
     ignoreDiagnostics,
diff --git a/src/index.ts b/src/index.ts
index 58a47cc9e..6b3d22cb6 100644
--- a/src/index.ts
+++ b/src/index.ts
@@ -301,6 +301,10 @@ export interface CreateOptions {
    * to get default, automatic behavior.
    */
   experimentalReplAwait?: boolean;
+  /**
+   * Runs at the start of CLI.
+   */
+  preprocessor?: string;
   /**
    * Override certain paths to be compiled and executed as CommonJS or ECMAScript modules.
    * When overridden, the tsconfig "module" and package.json "type" fields are overridden, and
diff --git a/src/repl.ts b/src/repl.ts
index 7b7c38367..f1221555c 100644
--- a/src/repl.ts
+++ b/src/repl.ts
@@ -1,13 +1,9 @@
 import type * as _diff from 'diff';
 import { homedir } from 'os';
 import { join } from 'path';
-import {
-  Recoverable,
-  ReplOptions,
-  REPLServer,
-  start as nodeReplStart,
-} from 'repl';
-import { Context, createContext, Script } from 'vm';
+import { Recoverable, ReplOptions, REPLServer } from 'repl';
+import { start as nodeReplStart } from 'pretty-repl';
+import { Context, Script } from 'vm';
 import { Service, CreateOptions, TSError, env } from './index';
 import { readFileSync, statSync } from 'fs';
 import { Console } from 'console';
@@ -386,7 +382,7 @@ export function createRepl(options: CreateReplOptions = {}) {
       eval: nodeEval,
       useGlobal: true,
       ...optionsOverride,
-    });
+    }) as REPLServer;
 
     nodeReplServer = repl;
     context = repl.context;
@@ -421,6 +417,13 @@ export function createRepl(options: CreateReplOptions = {}) {
           .map((name) => `declare import ${name} = require('${name}')`)
           .join(';')}\n`;
       }
+      if (service!.options.preprocessor) {
+        const preprocessorContent = readFileSync(
+          service!.options.preprocessor,
+          'utf8'
+        );
+        state.input += `${preprocessorContent}; void 0;\n`;
+      }
     }
 
     reset();
diff --git a/src/test/helpers/preprocessor.ts b/src/test/helpers/preprocessor.ts
new file mode 100644
index 000000000..ff1442213
--- /dev/null
+++ b/src/test/helpers/preprocessor.ts
@@ -0,0 +1,5 @@
+export const PreprocessorEnabled = true;
+
+export function isPreprocessorEnabled() {
+  return PreprocessorEnabled;
+}
diff --git a/yarn.lock b/yarn.lock
index 359b2fa03..0a9b40db5 100644
--- a/yarn.lock
+++ b/yarn.lock
@@ -924,7 +924,7 @@ __metadata:
   languageName: node
   linkType: hard
 
-"ansi-regex@npm:^5.0.1":
+"ansi-regex@npm:^5.0.0, ansi-regex@npm:^5.0.1":
   version: 5.0.1
   resolution: "ansi-regex@npm:5.0.1"
   checksum: 2aa4bb54caf2d622f1afdad09441695af2a83aa3fe8b8afa581d205e57ed4261c183c4d3877cee25794443fde5876417d859c108078ab788d6af7e4fe52eb66b
@@ -1261,7 +1261,17 @@ __metadata:
   languageName: node
   linkType: hard
 
-"chalk@npm:^4.0.0":
+"chalk@npm:^3.0.0":
+  version: 3.0.0
+  resolution: "chalk@npm:3.0.0"
+  dependencies:
+    ansi-styles: ^4.1.0
+    supports-color: ^7.1.0
+  checksum: 8e3ddf3981c4da405ddbd7d9c8d91944ddf6e33d6837756979f7840a29272a69a5189ecae0ff84006750d6d1e92368d413335eab4db5476db6e6703a1d1e0505
+  languageName: node
+  linkType: hard
+
+"chalk@npm:^4.0.0, chalk@npm:^4.1.1":
   version: 4.1.2
   resolution: "chalk@npm:4.1.2"
   dependencies:
@@ -1676,6 +1686,17 @@ __metadata:
   languageName: node
   linkType: hard
 
+"emphasize@npm:^3.0.0":
+  version: 3.0.0
+  resolution: "emphasize@npm:3.0.0"
+  dependencies:
+    chalk: ^3.0.0
+    highlight.js: ~9.12.0
+    lowlight: ~1.9.0
+  checksum: fef6b2ff83edc12863fa85dc4e0dbf075fbc3de8cc8cb67bdc65c7967e5e49057d6f58fed4c199c91720aba11317b21a1c1a7b0a2a845bd4b9e180586ed13f4a
+  languageName: node
+  linkType: hard
+
 "encoding@npm:^0.1.13":
   version: 0.1.13
   resolution: "encoding@npm:0.1.13"
@@ -1808,6 +1829,15 @@ __metadata:
   languageName: node
   linkType: hard
 
+"fault@npm:^1.0.2":
+  version: 1.0.4
+  resolution: "fault@npm:1.0.4"
+  dependencies:
+    format: ^0.2.0
+  checksum: 5ac610d8b09424e0f2fa8cf913064372f2ee7140a203a79957f73ed557c0e79b1a3d096064d7f40bde8132a69204c1fe25ec23634c05c6da2da2039cff26c4e7
+  languageName: node
+  linkType: hard
+
 "figures@npm:^5.0.0":
   version: 5.0.0
   resolution: "figures@npm:5.0.0"
@@ -1888,6 +1918,13 @@ __metadata:
   languageName: node
   linkType: hard
 
+"format@npm:^0.2.0":
+  version: 0.2.2
+  resolution: "format@npm:0.2.2"
+  checksum: 646a60e1336250d802509cf24fb801e43bd4a70a07510c816fa133aa42cdbc9c21e66e9cc0801bb183c5b031c9d68be62e7fbb6877756e52357850f92aa28799
+  languageName: node
+  linkType: hard
+
 "fromentries@npm:^1.2.0":
   version: 1.3.2
   resolution: "fromentries@npm:1.3.2"
@@ -2078,6 +2115,13 @@ __metadata:
   languageName: node
   linkType: hard
 
+"highlight.js@npm:~9.12.0":
+  version: 9.12.0
+  resolution: "highlight.js@npm:9.12.0"
+  checksum: 46b357bdaac95da903736222f1662b1e1423d35c954407bf18ed35f9f2aa87947e28d83cada2a887105d0e95990199ae11bd8a448b7bf0bb3331b9efcd136037
+  languageName: node
+  linkType: hard
+
 "html-escaper@npm:^2.0.0":
   version: 2.0.2
   resolution: "html-escaper@npm:2.0.2"
@@ -2609,6 +2653,16 @@ __metadata:
   languageName: node
   linkType: hard
 
+"lowlight@npm:~1.9.0":
+  version: 1.9.2
+  resolution: "lowlight@npm:1.9.2"
+  dependencies:
+    fault: ^1.0.2
+    highlight.js: ~9.12.0
+  checksum: a83edeab0a696733e88bde2e55e407227189969fa2084701b69fbebf38f1763584f802cd66df2c5834e7e56533b1e81f27d610d60868202215b1de9d3a77c149
+  languageName: node
+  linkType: hard
+
 "lru-cache@npm:^6.0.0":
   version: 6.0.0
   resolution: "lru-cache@npm:6.0.0"
@@ -3223,6 +3277,18 @@ __metadata:
   languageName: node
   linkType: hard
 
+"pretty-repl@npm:^3.1.1":
+  version: 3.1.1
+  resolution: "pretty-repl@npm:3.1.1"
+  dependencies:
+    ansi-regex: ^5.0.0
+    chalk: ^4.1.1
+    emphasize: ^3.0.0
+    strip-ansi: ^6.0.0
+  checksum: f4e54e079979cb7f536fd1907262fff39dc15ab13a366335dfcad15474dc3e8f41967bd5cb1dbe406281b1770b6fb2a43201710f5c9f9ac7986693e629df88e4
+  languageName: node
+  linkType: hard
+
 "process-on-spawn@npm:^1.0.0":
   version: 1.0.0
   resolution: "process-on-spawn@npm:1.0.0"
@@ -3832,6 +3898,7 @@ __metadata:
     make-error: ^1.1.1
     nyc: ^15.0.1
     outdent: ^0.8.0
+    pretty-repl: ^3.1.1
     proper-lockfile: ^4.1.2
     proxyquire: ^2.0.0
     rimraf: ^3.0.0