diff --git a/CHANGELOG.md b/CHANGELOG.md
index c58f91766..b7c8d5f9d 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -2,6 +2,13 @@
 
 All notable changes to this project will be documented in this file. See [standard-version](https://github.com/conventional-changelog/standard-version) for commit guidelines.
 
+### [1.14.2](https://github.com/oclif/core/compare/v1.14.1...v1.14.2) (2022-08-18)
+
+
+### Bug Fixes
+
+* add overloads to enum flag ([799455b](https://github.com/oclif/core/commit/799455bbb526b221c806bf8feff6b625dcf50a56))
+
 ### [1.14.1](https://github.com/oclif/core/compare/v1.14.0...v1.14.1) (2022-08-16)
 
 
diff --git a/package.json b/package.json
index c1e1fc2df..60a4fa268 100644
--- a/package.json
+++ b/package.json
@@ -1,7 +1,7 @@
 {
   "name": "@oclif/core",
   "description": "base library for oclif CLIs",
-  "version": "1.14.1",
+  "version": "1.14.2",
   "author": "Salesforce",
   "bugs": "https://github.com/oclif/core/issues",
   "dependencies": {
diff --git a/src/flags.ts b/src/flags.ts
index ccc4dcb21..339584fb0 100644
--- a/src/flags.ts
+++ b/src/flags.ts
@@ -1,4 +1,4 @@
-import {OptionFlag, Definition, BooleanFlag, EnumFlagOptions} from './interfaces'
+import {OptionFlag, Definition, BooleanFlag, EnumFlagOptions, Default} from './interfaces'
 import * as Parser from './parser'
 import Command from './command'
 
@@ -12,7 +12,11 @@ export function option<T>(options: {parse: OptionFlag<T>['parse']} & Partial<Opt
   return build<T>(options)()
 }
 
-const _enum = <T = string>(opts: EnumFlagOptions<T>): OptionFlag<T> => {
+export function _enum<T = string>(opts: EnumFlagOptions<T> & {multiple: true} & ({required: true} | { default: Default<T> })): OptionFlag<T[]>
+export function _enum<T = string>(opts: EnumFlagOptions<T> & {multiple: true}): OptionFlag<T[] | undefined>
+export function _enum<T = string>(opts: EnumFlagOptions<T> & ({required: true} | { default: Default<T> })): OptionFlag<T>
+export function _enum<T = string>(opts: EnumFlagOptions<T>): OptionFlag<T | undefined>
+export function _enum<T = string>(opts: EnumFlagOptions<T>): OptionFlag<T> | OptionFlag<T[]> | OptionFlag<T | undefined> | OptionFlag<T[] | undefined> {
   return build<T>({
     async parse(input) {
       if (!opts.options.includes(input)) throw new Error(`Expected --${this.name}=${input} to be one of: ${opts.options.join(', ')}`)
@@ -20,7 +24,7 @@ const _enum = <T = string>(opts: EnumFlagOptions<T>): OptionFlag<T> => {
     },
     helpValue: `(${opts.options.join('|')})`,
     ...opts,
-  })() as OptionFlag<T>
+  })()
 }
 
 export {_enum as enum}
diff --git a/src/parser/flags.ts b/src/parser/flags.ts
index 840a03e8e..eaa8bcd80 100644
--- a/src/parser/flags.ts
+++ b/src/parser/flags.ts
@@ -75,7 +75,7 @@ export function directory(opts: { exists?: boolean } & Partial<OptionFlag<string
 
 export function file(opts: Partial<OptionFlag<string>> & { exists?: boolean } & {multiple: true} & ({required: true} | { default: Default<string> })): OptionFlag<string[]>
 export function file(opts: Partial<OptionFlag<string>> & { exists?: boolean } & {multiple: true}): OptionFlag<string[] | undefined>
-export function file(opts: { exists?: boolean } & Partial<OptionFlag<string>> & ({required: true} | { default: string })): OptionFlag<string>
+export function file(opts: { exists?: boolean } & Partial<OptionFlag<string>> & ({required: true} | { default: Default<string> })): OptionFlag<string>
 export function file(opts?: { exists?: boolean } & Partial<OptionFlag<string>>): OptionFlag<string | undefined>
 export function file(opts: { exists?: boolean } & Partial<OptionFlag<string>> = {}): OptionFlag<string> | OptionFlag<string[]> | OptionFlag<string | undefined> | OptionFlag<string[] | undefined> {
   return build<string>({