diff --git a/__tests__/bin/vip-app-deploy-validate.js b/__tests__/bin/vip-app-deploy-validate.js
new file mode 100644
index 000000000..dd44336c8
--- /dev/null
+++ b/__tests__/bin/vip-app-deploy-validate.js
@@ -0,0 +1,127 @@
+import { appDeployValidateCmd } from '../../src/bin/vip-app-deploy-validate';
+import { getFileMeta } from '../../src/lib/client-file-uploader';
+import * as exit from '../../src/lib/cli/exit';
+import { validateFile } from '../../src/lib/custom-deploy/custom-deploy';
+import {
+	validateName,
+	validateZipFile,
+	validateTarFile,
+} from '../../src/lib/validations/custom-deploy';
+
+jest.mock( '../../src/lib/client-file-uploader', () => ( {
+	...jest.requireActual( '../../src/lib/client-file-uploader' ),
+	getFileMeta: jest
+		.fn()
+		.mockResolvedValue( { fileName: '/vip/skeleton.zip', basename: 'skeleton.zip' } ),
+} ) );
+
+jest.mock( '../../src/lib/custom-deploy/custom-deploy', () => ( {
+	validateFile: jest.fn(),
+} ) );
+
+jest.mock( '../../src/lib/validations/custom-deploy', () => {
+	return {
+		...jest.requireActual( '../../src/lib/validations/custom-deploy' ),
+		validateZipFile: jest.fn(),
+		validateTarFile: jest.fn(),
+	};
+} );
+
+jest.mock( '../../src/lib/cli/command', () => {
+	const commandMock = {
+		argv: () => commandMock,
+		examples: () => commandMock,
+		option: () => commandMock,
+		command: () => commandMock,
+	};
+	return jest.fn( () => commandMock );
+} );
+
+const exitSpy = jest.spyOn( exit, 'withError' );
+jest.spyOn( process, 'exit' ).mockImplementation( () => {} );
+jest.spyOn( console, 'error' ).mockImplementation( () => {} );
+
+const opts = {
+	app: {
+		id: 1,
+		organization: {
+			id: 2,
+		},
+	},
+	env: {
+		id: 3,
+		type: 'develop',
+	},
+	force: true,
+};
+
+describe( 'vip-app-deploy-validate', () => {
+	describe( 'validateName', () => {
+		beforeEach( async () => {
+			exitSpy.mockClear();
+		} );
+
+		it.each( [ '!client-mu-plugins', '..vip-go-skeleton', '*test' ] )(
+			'fails if the file has has invalid characters for directories',
+			basename => {
+				validateName( basename, true );
+				expect( exitSpy ).toHaveBeenCalledWith(
+					`Filename ${ basename } contains disallowed characters: [!:*?"<>|\'/^\\.\\.]+`
+				);
+			}
+		);
+
+		it.each( [ 'client-mu-plugins', 'vip-go-skeleton/', '._vip-go-skeleton' ] )(
+			'passes if the file has has valid characters for directories',
+			basename => {
+				validateName( basename, true );
+				expect( exitSpy ).not.toHaveBeenCalled();
+			}
+		);
+
+		it.each( [ 'client-mu-/plugins.php', 'vip-?config.php' ] )(
+			'fails if the file has has invalid characters for non-directories',
+			basename => {
+				validateName( basename, false );
+				expect( exitSpy ).toHaveBeenCalledWith(
+					`Filename ${ basename } contains disallowed characters: [!/:*?"<>|\'/^\\.\\.]+`
+				);
+			}
+		);
+
+		it.each( [ 'client-mu-plugins.php', 'vip-config.php' ] )(
+			'passes if the file has has valid characters for non-directories',
+			basename => {
+				validateName( basename, false );
+				expect( exitSpy ).not.toHaveBeenCalled();
+			}
+		);
+	} );
+
+	describe( 'appDeployValidateCmd', () => {
+		beforeEach( () => {
+			jest.clearAllMocks();
+		} );
+
+		it( 'should call expected functions (zip)', async () => {
+			const args = [ '/vip/skeleton.zip' ];
+			getFileMeta.mockResolvedValue( { fileName: '/vip/skeleton.zip', basename: 'skeleton.zip' } );
+
+			await appDeployValidateCmd( args, opts );
+			expect( validateFile ).toHaveBeenCalledTimes( 1 );
+			expect( validateZipFile ).toHaveBeenCalledTimes( 1 );
+		} );
+
+		it( 'should call expected functions (tar)', async () => {
+			const args = [ '/vip/foo.tar.gz' ];
+			getFileMeta.mockResolvedValue( {
+				fileName: '/vip/foo.tar.gz',
+				basename: 'foo.tar.gz',
+			} );
+
+			await appDeployValidateCmd( args, opts );
+			expect( validateFile ).toHaveBeenCalledTimes( 1 );
+			expect( validateTarFile ).toHaveBeenCalledTimes( 1 );
+		} );
+	} );
+} );
diff --git a/__tests__/bin/vip-app-deploy.js b/__tests__/bin/vip-app-deploy.js
index d6d2c085c..70e33a0ea 100644
--- a/__tests__/bin/vip-app-deploy.js
+++ b/__tests__/bin/vip-app-deploy.js
@@ -36,6 +36,7 @@ jest.mock( '../../src/lib/cli/command', () => {
 		argv: () => commandMock,
 		examples: () => commandMock,
 		option: () => commandMock,
+		command: () => commandMock,
 	};
 	return jest.fn( () => commandMock );
 } );
@@ -70,7 +71,7 @@ describe( 'vip-app-deploy', () => {
 			async basename => {
 				validateFilename( basename );
 				expect( exitSpy ).toHaveBeenCalledWith(
-					'Error: The characters used in the name of a file for custom deploys are limited to [0-9,a-z,A-Z,-,_,.]'
+					`Filename ${ basename } contains disallowed characters: [0-9,a-z,A-Z,-,_,.]`
 				);
 			}
 		);
diff --git a/src/lib/custom-deploy/custom-deploy.ts b/src/lib/custom-deploy/custom-deploy.ts
index dbf8ea6fc..354ef7f69 100644
--- a/src/lib/custom-deploy/custom-deploy.ts
+++ b/src/lib/custom-deploy/custom-deploy.ts
@@ -1,6 +1,5 @@
 import fs from 'fs';
 import gql from 'graphql-tag';
-import debugLib from 'debug';
 
 import API from '../../lib/api';
 import * as exit from '../../lib/cli/exit';
diff --git a/src/lib/validations/custom-deploy.ts b/src/lib/validations/custom-deploy.ts
index 4b8713ced..debd137de 100644
--- a/src/lib/validations/custom-deploy.ts
+++ b/src/lib/validations/custom-deploy.ts
@@ -2,12 +2,9 @@ import path from 'path';
 import AdmZip from 'adm-zip';
 import { constants } from 'node:fs';
 import * as tar from 'tar';
-import debugLib from 'debug';
 
 import * as exit from '../../lib/cli/exit';
 
-const debug = debugLib( '@automattic/vip:bin:vip-lib-deploy-validate' );
-
 interface TarEntry {
 	path: string;
 	type: string;
@@ -20,7 +17,7 @@ const errorMessages = {
 	singleRootDir: 'The compressed file must contain a single root directory!',
 	invalidExt: 'Invalid file extension. Please provide a .zip, .tar.gz, or a .tgz file.',
 	invalidChars: ( filename: string, invalidChars: string ) =>
-		`Filename "${ filename }" contains disallowed characters: ${ invalidChars }`,
+		`Filename ${ filename } contains disallowed characters: ${ invalidChars }`,
 };
 const symlinkIgnorePattern = /\/node_modules\/[^/]+\/\.bin\//;
 const macosxDir = '__MACOSX';
@@ -52,7 +49,7 @@ export function validateFilename( filename: string ) {
 	const re = /^[a-z0-9\-_.]+$/i;
 
 	if ( ! re.test( filename ) ) {
-		exit.withError( errorMessages.invalidChars( filename, re.toString() ) );
+		exit.withError( errorMessages.invalidChars( filename, '[0-9,a-z,A-Z,-,_,.]' ) );
 	}
 }
 
@@ -62,13 +59,13 @@ export function validateFilename( filename: string ) {
  * @param {string} name The name of the file
  * @param {bool} isDirectory Whether the file is a directory
  */
-function validateName( name: string, isDirectory: boolean ) {
+export function validateName( name: string, isDirectory: boolean ) {
 	if ( name.startsWith( '._' ) ) {
 		return;
 	}
 
 	const invalidCharsPattern = isDirectory ? /[!\:*?"<>|']|^\.\..*$/ : /[!\/:*?"<>|']|^\.\..*$/;
-	const errorMessage = errorMessages.invalidChars( name, invalidCharsPattern.toString() );
+	const errorMessage = errorMessages.invalidChars( name, isDirectory ? '[!:*?"<>|\'/^\\.\\.]+' : '[!/:*?"<>|\'/^\\.\\.]+' );
 	if ( invalidCharsPattern.test( name ) ) {
 		exit.withError( errorMessage );
 	}