diff --git a/package.json b/package.json
index 895a8ad3293..375c82e8178 100644
--- a/package.json
+++ b/package.json
@@ -39,6 +39,7 @@
     "@iconify/json": "^2.1.62",
     "@rollup/plugin-json": "^4.1.0",
     "@rollup/plugin-replace": "^4.0.0",
+    "@type-challenges/utils": "^0.1.1",
     "@types/fs-extra": "^9.0.13",
     "@types/js-yaml": "^4.0.5",
     "@types/md5": "^2.3.2",
diff --git a/packages/shared/until/index.test.ts b/packages/shared/until/index.test.ts
index eb75f84956a..e7af354bf67 100644
--- a/packages/shared/until/index.test.ts
+++ b/packages/shared/until/index.test.ts
@@ -1,5 +1,7 @@
+import type { Ref } from 'vue-demi'
 import { ref } from 'vue-demi'
 import { invoke } from '@vueuse/shared'
+import type { Equal, Expect } from '@type-challenges/utils'
 import { until } from '.'
 
 describe('until', () => {
@@ -9,8 +11,8 @@ describe('until', () => {
 
       invoke(async () => {
         expect(r.value).toBe(0)
-        await until(r).toBe(1)
-        expect(r.value).toBe(1)
+        const x = await until(r).toBe(1)
+        expect(x).toBe(1)
         resolve()
       }).catch(reject)
 
@@ -26,8 +28,8 @@ describe('until', () => {
 
       invoke(async () => {
         expect(r.value).toBe(0)
-        await until(r).changedTimes(3)
-        expect(r.value).toBe(3)
+        const x = await until(r).changedTimes(3)
+        expect(x).toBe(3)
         resolve()
       }).catch(reject)
 
@@ -45,8 +47,8 @@ describe('until', () => {
 
       invoke(async () => {
         expect(r.value).toBe(0)
-        await until(r).not.toBe(0)
-        expect(r.value).toBe(1)
+        const x = await until(r).not.toBe(0)
+        expect(x).toBe(1)
         resolve()
       }).catch(reject)
 
@@ -62,8 +64,8 @@ describe('until', () => {
 
       invoke(async () => {
         expect(r.value).toBe(null)
-        await until(r).not.toBeNull()
-        expect(r.value).toBe(1)
+        const x = await until(r).not.toBeNull()
+        expect(x).toBe(1)
         resolve()
       }).catch(reject)
 
@@ -79,8 +81,8 @@ describe('until', () => {
 
       invoke(async () => {
         expect(r.value).toEqual([1, 2, 3])
-        await until(r).toContains(4, { deep: true })
-        expect(r.value).toEqual([1, 2, 3, 4])
+        const x = await until(r).toContains(4, { deep: true })
+        expect(x).toEqual([1, 2, 3, 4])
         resolve()
       }).catch(reject)
 
@@ -96,8 +98,8 @@ describe('until', () => {
 
       invoke(async () => {
         expect(r.value).toEqual([1, 2, 3])
-        await until(r).not.toContains(2, { deep: true })
-        expect(r.value).toEqual([1])
+        const x = await until(r).not.toContains(2, { deep: true })
+        expect(x).toEqual([1])
         resolve()
       }).catch(reject)
 
@@ -107,4 +109,65 @@ describe('until', () => {
       }, 100)
     })
   })
+
+  it('should immediately timeout', () => {
+    return new Promise<void>((resolve, reject) => {
+      const r = ref(0)
+
+      invoke(async () => {
+        expect(r.value).toBe(0)
+        const x = await until(r).toBe(1, { timeout: 0 })
+        expect(x).toBe(0)
+        resolve()
+      }).catch(reject)
+
+      setTimeout(() => {
+        r.value = 1
+      }, 100)
+    })
+  })
+
+  it('should type check', () => {
+    async () => {
+      const x = ref<'x'>()
+      // type checks are done this way to prevent unused variable warnings
+      // and duplicate name warnings
+      'test' as any as Expect<Equal<typeof x, Ref<'x' | undefined>>>
+
+      const one = await until(x).toBe(1 as const)
+      'test' as any as Expect<Equal<typeof one, 1>>
+
+      const xTruthy = await until(x).toBeTruthy()
+      'test' as any as Expect<Equal<typeof xTruthy, 'x'>>
+
+      const xFalsy = await until(x).not.toBeTruthy()
+      'test' as any as Expect<Equal<typeof xFalsy, undefined>>
+
+      const xUndef = await until(x).toBeUndefined()
+      'test' as any as Expect<Equal<typeof xUndef, undefined>>
+
+      const xNotUndef = await until(x).not.toBeUndefined()
+      'test' as any as Expect<Equal<typeof xNotUndef, 'x'>>
+
+      const y = ref<'y' | null>(null)
+      'test' as any as Expect<Equal<typeof y, Ref<'y' | null>>>
+
+      const yNull = await until(y).toBeNull()
+      'test' as any as Expect<Equal<typeof yNull, null>>
+
+      const yNotNull = await until(y).not.toBeNull()
+      'test' as any as Expect<Equal<typeof yNotNull, 'y'>>
+
+      const z = ref<1 | 2 | 3>(1)
+      'test' as any as Expect<Equal<typeof z, Ref<1 | 2 | 3>>>
+
+      const is1 = (x: number): x is 1 => x === 1
+
+      const z1 = await until(z).toMatch(is1)
+      'test' as any as Expect<Equal<typeof z1, 1>>
+
+      const zNot1 = await until(z).not.toMatch(is1)
+      'test' as any as Expect<Equal<typeof zNot1, 2 | 3>>
+    }
+  })
 })
diff --git a/packages/shared/until/index.ts b/packages/shared/until/index.ts
index 59f7098e2a3..499d8f1b610 100644
--- a/packages/shared/until/index.ts
+++ b/packages/shared/until/index.ts
@@ -1,5 +1,5 @@
 import type { WatchOptions, WatchSource } from 'vue-demi'
-import { unref, watch } from 'vue-demi'
+import { isRef, unref, watch } from 'vue-demi'
 import type { ElementOf, MaybeRef, ShallowUnwrapRef } from '../utils'
 import { promiseTimeout } from '../utils'
 
@@ -34,29 +34,35 @@ export interface UntilToMatchOptions {
   deep?: WatchOptions['deep']
 }
 
-export interface UntilBaseInstance<T> {
+export interface UntilBaseInstance<T, Not extends boolean = false> {
+  toMatch<U extends T = T>(
+    condition: (v: T) => v is U,
+    options?: UntilToMatchOptions
+  ): Not extends true ? Promise<Exclude<T, U>> : Promise<U>
   toMatch(
     condition: (v: T) => boolean,
     options?: UntilToMatchOptions
-  ): Promise<void>
-  changed(options?: UntilToMatchOptions): Promise<void>
-  changedTimes(n?: number, options?: UntilToMatchOptions): Promise<void>
+  ): Promise<T>
+  changed(options?: UntilToMatchOptions): Promise<T>
+  changedTimes(n?: number, options?: UntilToMatchOptions): Promise<T>
 }
 
-export interface UntilValueInstance<T> extends UntilBaseInstance<T> {
-  readonly not: UntilValueInstance<T>
+type Falsy = false | void | null | undefined | 0 | 0n | ''
+
+export interface UntilValueInstance<T, Not extends boolean = false> extends UntilBaseInstance<T, Not> {
+  readonly not: UntilValueInstance<T, Not extends true ? false : true>
 
-  toBe<P = T>(value: MaybeRef<T | P>, options?: UntilToMatchOptions): Promise<void>
-  toBeTruthy(options?: UntilToMatchOptions): Promise<void>
-  toBeNull(options?: UntilToMatchOptions): Promise<void>
-  toBeUndefined(options?: UntilToMatchOptions): Promise<void>
-  toBeNaN(options?: UntilToMatchOptions): Promise<void>
+  toBe<P = T>(value: MaybeRef<P>, options?: UntilToMatchOptions): Not extends true ? Promise<T> : Promise<P>
+  toBeTruthy(options?: UntilToMatchOptions): Not extends true ? Promise<T & Falsy> : Promise<Exclude<T, Falsy>>
+  toBeNull(options?: UntilToMatchOptions): Not extends true ? Promise<Exclude<T, null>> : Promise<null>
+  toBeUndefined(options?: UntilToMatchOptions): Not extends true ? Promise<Exclude<T, undefined>> : Promise<undefined>
+  toBeNaN(options?: UntilToMatchOptions): Promise<T>
 }
 
 export interface UntilArrayInstance<T> extends UntilBaseInstance<T> {
   readonly not: UntilArrayInstance<T>
 
-  toContains(value: MaybeRef<ElementOf<ShallowUnwrapRef<T>>>, options?: UntilToMatchOptions): Promise<void>
+  toContains(value: MaybeRef<ElementOf<ShallowUnwrapRef<T>>>, options?: UntilToMatchOptions): Promise<T>
 }
 
 /**
@@ -80,15 +86,15 @@ export function until<T>(r: any): any {
   function toMatch(
     condition: (v: any) => boolean,
     { flush = 'sync', deep = false, timeout, throwOnTimeout }: UntilToMatchOptions = {},
-  ): Promise<void> {
+  ): Promise<T> {
     let stop: Function | null = null
-    const watcher = new Promise<void>((resolve) => {
+    const watcher = new Promise<T>((resolve) => {
       stop = watch(
         r,
         (v) => {
-          if (condition(v) === !isNot) {
+          if (condition(v) !== isNot) {
             stop?.()
-            resolve()
+            resolve(v)
           }
         },
         {
@@ -100,11 +106,11 @@ export function until<T>(r: any): any {
     })
 
     const promises = [watcher]
-    if (timeout) {
+    if (timeout != null) {
       promises.push(
-        promiseTimeout(timeout, throwOnTimeout).finally(() => {
-          stop?.()
-        }),
+        promiseTimeout(timeout, throwOnTimeout)
+          .then(() => unref(r))
+          .finally(() => stop?.()),
       )
     }
 
@@ -112,7 +118,41 @@ export function until<T>(r: any): any {
   }
 
   function toBe<P>(value: MaybeRef<P | T>, options?: UntilToMatchOptions) {
-    return toMatch(v => v === unref(value), options)
+    if (!isRef(value))
+      return toMatch(v => v === value, options)
+
+    const { flush = 'sync', deep = false, timeout, throwOnTimeout } = options ?? {}
+    let stop: Function | null = null
+    const watcher = new Promise<T>((resolve) => {
+      stop = watch(
+        [r, value],
+        ([v1, v2]) => {
+          if (isNot !== (v1 === v2)) {
+            stop?.()
+            resolve(v1)
+          }
+        },
+        {
+          flush,
+          deep,
+          immediate: true,
+        },
+      )
+    })
+
+    const promises = [watcher]
+    if (timeout != null) {
+      promises.push(
+        promiseTimeout(timeout, throwOnTimeout)
+          .then(() => unref(r))
+          .finally(() => {
+            stop?.()
+            return unref(r)
+          }),
+      )
+    }
+
+    return Promise.race(promises)
   }
 
   function toBeTruthy(options?: UntilToMatchOptions) {
@@ -167,13 +207,13 @@ export function until<T>(r: any): any {
     return instance
   }
   else {
-    const instance: UntilValueInstance<T> = {
+    const instance: UntilValueInstance<T, boolean> = {
       toMatch,
       toBe,
-      toBeTruthy,
-      toBeNull,
+      toBeTruthy: toBeTruthy as any,
+      toBeNull: toBeNull as any,
       toBeNaN,
-      toBeUndefined,
+      toBeUndefined: toBeUndefined as any,
       changed,
       changedTimes,
       get not() {
diff --git a/pnpm-lock.yaml b/pnpm-lock.yaml
index 61d8281350f..a1f30c6d2d2 100644
--- a/pnpm-lock.yaml
+++ b/pnpm-lock.yaml
@@ -15,6 +15,7 @@ importers:
       '@iconify/json': ^2.1.62
       '@rollup/plugin-json': ^4.1.0
       '@rollup/plugin-replace': ^4.0.0
+      '@type-challenges/utils': ^0.1.1
       '@types/fs-extra': ^9.0.13
       '@types/js-yaml': ^4.0.5
       '@types/md5': ^2.3.2
@@ -79,6 +80,7 @@ importers:
       '@iconify/json': 2.1.62
       '@rollup/plugin-json': 4.1.0_rollup@2.75.6
       '@rollup/plugin-replace': 4.0.0_rollup@2.75.6
+      '@type-challenges/utils': 0.1.1
       '@types/fs-extra': 9.0.13
       '@types/js-yaml': 4.0.5
       '@types/md5': 2.3.2
@@ -2503,6 +2505,10 @@ packages:
     engines: {node: '>= 10'}
     dev: true
 
+  /@type-challenges/utils/0.1.1:
+    resolution: {integrity: sha512-A7ljYfBM+FLw+NDyuYvGBJiCEV9c0lPWEAdzfOAkb3JFqfLl0Iv/WhWMMARHiRKlmmiD1g8gz/507yVvHdQUYA==}
+    dev: true
+
   /@types/chai-subset/1.3.3:
     resolution: {integrity: sha512-frBecisrNGz+F4T6bcc+NLeolfiojh5FxW2klu669+8BARtyQv2C/GkNW6FUodVe4BroGMP/wER/YDGc7rEllw==}
     dependencies: