diff --git a/src/parse.ts b/src/parse.ts
index 04e1cb3..e4e0be2 100644
--- a/src/parse.ts
+++ b/src/parse.ts
@@ -47,6 +47,7 @@ export class Parser<T extends ParserInput, TFlags extends OutputFlags<T['flags']
   private readonly raw: ParsingToken[] = []
   private readonly booleanFlags: { [k: string]: Flags.IBooleanFlag<any> }
   private readonly context: any
+  private currentFlag?: Flags.IOptionFlag<any>
   constructor(private readonly input: T) {
     const {pickBy} = m.util
     this.context = input.context || {}
@@ -92,6 +93,7 @@ export class Parser<T extends ParserInput, TFlags extends OutputFlags<T['flags']
       }
       const flag = this.input.flags[name]
       if (flag.type === 'option') {
+        this.currentFlag = flag
         let input
         if (long || arg.length < 3) {
           input = this.argv.shift()
@@ -125,6 +127,10 @@ export class Parser<T extends ParserInput, TFlags extends OutputFlags<T['flags']
         }
         // not actually a flag if it reaches here so parse as an arg
       }
+      if (parsingFlags && this.currentFlag && this.currentFlag.multiple) {
+        this.raw.push({type: 'flag', flag: this.currentFlag.name, input})
+        continue
+      }
       // not a flag, parse as arg
       const arg = this.input.args[this._argTokens.length]
       if (arg) arg.input = input
diff --git a/test/parse.test.ts b/test/parse.test.ts
index fe43694..ea20bb2 100644
--- a/test/parse.test.ts
+++ b/test/parse.test.ts
@@ -277,6 +277,33 @@ See more help with --help`)
     // })
   })
 
+  describe('flag with multiple inputs', () => {
+    it('flag multiple with flag in the middle', () => {
+      const out = parse(['--foo=bar', '--foo', '100', '--hello', 'world'], {
+        flags: {foo: flags.string({multiple: true}), hello: flags.string()},
+      })
+      expect(out.flags).to.deep.include({foo: ['bar', '100']})
+      expect(out.flags).to.deep.include({hello: 'world'})
+    })
+
+    it('flag multiple without flag in the middle', () => {
+      const out = parse(['--foo', './a.txt', './b.txt', './c.txt', '--hello', 'world'], {
+        flags: {foo: flags.string({multiple: true}), hello: flags.string()},
+      })
+      expect(out.flags).to.deep.include({foo: ['./a.txt', './b.txt', './c.txt']})
+      expect(out.flags).to.deep.include({hello: 'world'})
+    })
+
+    it('flag multiple with arguments', () => {
+      const out = parse(['--foo', './a.txt', './b.txt', './c.txt', '--', '15'], {
+        args: [{name: 'num'}],
+        flags: {foo: flags.string({multiple: true})},
+      })
+      expect(out.flags).to.deep.include({foo: ['./a.txt', './b.txt', './c.txt']})
+      expect(out.args).to.deep.include({num: '15'})
+    })
+  })
+
   describe('defaults', () => {
     it('defaults', () => {
       const out = parse([], {