diff --git a/types/expect-puppeteer/index.d.ts b/types/expect-puppeteer/index.d.ts
index 72283c05e4be68..5a4a2d9e8a04e1 100644
--- a/types/expect-puppeteer/index.d.ts
+++ b/types/expect-puppeteer/index.d.ts
@@ -51,7 +51,7 @@ interface ExpectPuppeteer {
 declare global {
     namespace jest {
         // tslint:disable-next-line no-empty-interface
-        interface Matchers<R> {
+        interface Matchers<R, T> {
             // These must all match the ExpectPuppeteer interface above.
             // We can't extend from it directly because some method names conflict in type-incompatible ways.
             toClick(selector: string, options?: ExpectToClickOptions): Promise<void>;
diff --git a/types/jest-axe/index.d.ts b/types/jest-axe/index.d.ts
index d04364c0fe7de1..4757c319c2d5e1 100644
--- a/types/jest-axe/index.d.ts
+++ b/types/jest-axe/index.d.ts
@@ -79,7 +79,7 @@ export const toHaveNoViolations: {
 
 declare global {
     namespace jest {
-        interface Matchers<R> {
+        interface Matchers<R, T> {
             toHaveNoViolations(): R;
         }
     }
diff --git a/types/jest-expect-message/index.d.ts b/types/jest-expect-message/index.d.ts
index ae9b85aea9cf9f..3ba5f5ceaf3249 100644
--- a/types/jest-expect-message/index.d.ts
+++ b/types/jest-expect-message/index.d.ts
@@ -8,6 +8,6 @@
 
 declare namespace jest {
     interface Expect {
-        <T = any>(actual: T, message: string): Matchers<T>;
+        <T = any>(actual: T, message: string): JestMatchers<T>;
     }
 }
diff --git a/types/jest-image-snapshot/index.d.ts b/types/jest-image-snapshot/index.d.ts
index 10d6a2a17dfc57..075e2c0506fd26 100644
--- a/types/jest-image-snapshot/index.d.ts
+++ b/types/jest-image-snapshot/index.d.ts
@@ -80,7 +80,7 @@ export function configureToMatchImageSnapshot(options: MatchImageSnapshotOptions
 
 declare global {
     namespace jest {
-        interface Matchers<R> {
+        interface Matchers<R, T> {
             toMatchImageSnapshot(options?: MatchImageSnapshotOptions): R;
         }
     }
diff --git a/types/jest-json-schema/index.d.ts b/types/jest-json-schema/index.d.ts
index cc9636a36df522..8fbcfaa8f44850 100644
--- a/types/jest-json-schema/index.d.ts
+++ b/types/jest-json-schema/index.d.ts
@@ -10,7 +10,7 @@ import * as ajv from 'ajv';
 
 declare global {
     namespace jest {
-        interface Matchers<R> {
+        interface Matchers<R, T> {
             toBeValidSchema(): R;
             toMatchSchema(schema: object): R;
         }
diff --git a/types/jest-matcher-one-of/index.d.ts b/types/jest-matcher-one-of/index.d.ts
index 63ab484473f378..4725d88a00c356 100644
--- a/types/jest-matcher-one-of/index.d.ts
+++ b/types/jest-matcher-one-of/index.d.ts
@@ -6,7 +6,7 @@
 
 /// <reference types="jest" />
 declare namespace jest {
-    interface Matchers<R> {
+    interface Matchers<R, T> {
         toBeOneOf(expected: any[]): R;
     }
 }
diff --git a/types/jest-specific-snapshot/index.d.ts b/types/jest-specific-snapshot/index.d.ts
index 25c168f5d26a73..b4b076fa556858 100644
--- a/types/jest-specific-snapshot/index.d.ts
+++ b/types/jest-specific-snapshot/index.d.ts
@@ -8,7 +8,7 @@
 
 declare global {
     namespace jest {
-        interface Matchers<R> {
+        interface Matchers<R, T> {
             toMatchSpecificSnapshot(snapshotFilename: string): R;
         }
     }
diff --git a/types/jest/index.d.ts b/types/jest/index.d.ts
index ade34870b60622..394e68d88891ab 100644
--- a/types/jest/index.d.ts
+++ b/types/jest/index.d.ts
@@ -23,6 +23,7 @@
 //                 ExE Boss <https://github.com/ExE-Boss>
 //                 Alex Bolenok <https://github.com/quassnoi>
 //                 Mario Beltrán Alarcón <https://github.com/Belco90>
+//                 Tony Hallett <https://github.com/tonyhallett>
 // Definitions: https://github.com/DefinitelyTyped/DefinitelyTyped
 // TypeScript Version: 3.0
 
@@ -396,8 +397,9 @@ declare namespace jest {
     }
 
     interface MatcherUtils {
-        readonly expand: boolean;
         readonly isNot: boolean;
+        readonly dontThrow: () => void;
+        readonly promise: string;
         utils: {
             readonly EXPECTED_COLOR: (text: string) => string;
             readonly RECEIVED_COLOR: (text: string) => string;
@@ -426,21 +428,23 @@ declare namespace jest {
          *  This is a deep-equality function that will return true if two objects have the same values (recursively).
          */
         equals(a: any, b: any): boolean;
+        [other: string]: any;
     }
 
     interface ExpectExtendMap {
         [key: string]: CustomMatcher;
     }
 
+    type MatcherContext = MatcherUtils & Readonly<MatcherState>;
     type CustomMatcher = (
-        this: MatcherUtils,
+        this: MatcherContext,
         received: any,
         ...actual: any[]
     ) => CustomMatcherResult | Promise<CustomMatcherResult>;
 
     interface CustomMatcherResult {
         pass: boolean;
-        message: string | (() => string);
+        message: () => string;
     }
 
     interface SnapshotSerializerOptions {
@@ -516,7 +520,15 @@ declare namespace jest {
          */
         stringContaining(str: string): any;
     }
-
+    interface MatcherState {
+        assertionCalls: number;
+        currentTestName: string;
+        expand: boolean;
+        expectedAssertionsNumber: number;
+        isExpectingAssertions?: boolean;
+        suppressedErrors: Error[];
+        testPath: string;
+    }
     /**
      * The `expect` function is used every time you want to test a value.
      * You will rarely call `expect` by itself.
@@ -528,7 +540,7 @@ declare namespace jest {
          *
          * @param actual The value to apply matchers against.
          */
-        <T = any>(actual: T): Matchers<T>;
+        <T = any>(actual: T): JestMatchers<T>;
         /**
          * Matches anything but null or undefined. You can use it inside `toEqual` or `toBeCalledWith` instead
          * of a literal value. For example, if you want to check that a mock function is called with a
@@ -601,9 +613,30 @@ declare namespace jest {
         stringContaining(str: string): any;
 
         not: InverseAsymmetricMatchers;
+
+        setState(state: object): void;
+        getState(): MatcherState & Record<string, any>;
     }
 
-    interface Matchers<R> {
+    type JestMatchers<T> = JestMatchersShape<Matchers<void, T>, Matchers<Promise<void>, T>>;
+
+    type JestMatchersShape<TNonPromise extends {} = {}, TPromise extends {} = {}> = {
+        /**
+         * Use resolves to unwrap the value of a fulfilled promise so any other
+         * matcher can be chained. If the promise is rejected the assertion fails.
+         */
+        resolves: AndNot<TPromise>,
+        /**
+         * Unwraps the reason of a rejected promise so any other matcher can be chained.
+         * If the promise is fulfilled the assertion fails.
+         */
+        rejects: AndNot<TPromise>
+    } & AndNot<TNonPromise>;
+    type AndNot<T> = T & {
+        not: T
+    };
+    // should be R extends void|Promise<void> but getting dtslint error
+    interface Matchers<R, T> {
         /**
          * Ensures the last call to a mock function was provided specific args.
          */
@@ -612,10 +645,6 @@ declare namespace jest {
          * Ensure that the last call to a mock function has returned a specified value.
          */
         lastReturnedWith(value: any): R;
-        /**
-         * If you know how to test something, `.not` lets you test its opposite.
-         */
-        not: Matchers<R>;
         /**
          * Ensure that a mock function is called with specific arguments on an Nth call.
          */
@@ -624,16 +653,6 @@ declare namespace jest {
          * Ensure that the nth call to a mock function has returned a specified value.
          */
         nthReturnedWith(n: number, value: any): R;
-        /**
-         * Use resolves to unwrap the value of a fulfilled promise so any other
-         * matcher can be chained. If the promise is rejected the assertion fails.
-         */
-        resolves: Matchers<Promise<R>>;
-        /**
-         * Unwraps the reason of a rejected promise so any other matcher can be chained.
-         * If the promise is fulfilled the assertion fails.
-         */
-        rejects: Matchers<Promise<R>>;
         /**
          * Checks that a value is what you expect. It uses `===` to check strict equality.
          * Don't use `toBe` with floating-point numbers.
@@ -816,7 +835,7 @@ declare namespace jest {
          * This ensures that a value matches the most recent snapshot with property matchers.
          * Check out [the Snapshot Testing guide](http://facebook.github.io/jest/docs/snapshot-testing.html) for more information.
          */
-        toMatchSnapshot<T extends { [P in keyof R]: any }>(propertyMatchers: Partial<T>, snapshotName?: string): R;
+        toMatchSnapshot<U extends { [P in keyof T]: any }>(propertyMatchers: Partial<U>, snapshotName?: string): R;
         /**
          * This ensures that a value matches the most recent snapshot.
          * Check out [the Snapshot Testing guide](http://facebook.github.io/jest/docs/snapshot-testing.html) for more information.
@@ -827,7 +846,7 @@ declare namespace jest {
          * Instead of writing the snapshot value to a .snap file, it will be written into the source code automatically.
          * Check out [the Snapshot Testing guide](http://facebook.github.io/jest/docs/snapshot-testing.html) for more information.
          */
-        toMatchInlineSnapshot<T extends { [P in keyof R]: any }>(propertyMatchers: Partial<T>, snapshot?: string): R;
+        toMatchInlineSnapshot<U extends { [P in keyof T]: any }>(propertyMatchers: Partial<U>, snapshot?: string): R;
         /**
          * This ensures that a value matches the most recent snapshot with property matchers.
          * Instead of writing the snapshot value to a .snap file, it will be written into the source code automatically.
@@ -869,6 +888,47 @@ declare namespace jest {
         toThrowErrorMatchingInlineSnapshot(snapshot?: string): R;
     }
 
+    type RemoveFirstFromTuple<T extends any[]> =
+    T['length'] extends 0 ? [] :
+        (((...b: T) => void) extends (a: any, ...b: infer I) => void ? I : []);
+
+    type Parameters<T extends (...args: any[]) => any> = T extends (...args: infer P) => any ? P : never;
+
+    interface AsymmetricMatcher {
+        asymmetricMatch(other: unknown): boolean;
+    }
+    type NonAsyncMatchers<TMatchers extends ExpectExtendMap> = {
+        [K in keyof TMatchers]: ReturnType<TMatchers[K]> extends Promise<CustomMatcherResult>? never: K
+    }[keyof TMatchers];
+    type CustomAsyncMatchers<TMatchers extends ExpectExtendMap> = {[K in NonAsyncMatchers<TMatchers>]: CustomAsymmetricMatcher<TMatchers[K]>};
+    type CustomAsymmetricMatcher<TMatcher extends (...args: any[]) => any> = (...args: RemoveFirstFromTuple<Parameters<TMatcher>>) => AsymmetricMatcher;
+
+    // should be TMatcherReturn extends void|Promise<void> but getting dtslint error
+    type CustomJestMatcher<TMatcher extends (...args: any[]) => any, TMatcherReturn> = (...args: RemoveFirstFromTuple<Parameters<TMatcher>>) => TMatcherReturn;
+
+    type ExpectProperties= {
+        [K in keyof Expect]: Expect[K]
+    };
+    // should be TMatcherReturn extends void|Promise<void> but getting dtslint error
+    // Use the `void` type for return types only. Otherwise, use `undefined`. See: https://github.com/Microsoft/dtslint/blob/master/docs/void-return.md
+    // have added issue https://github.com/microsoft/dtslint/issues/256 - Cannot have type union containing void ( to be used as return type only
+    type ExtendedMatchers<TMatchers extends ExpectExtendMap, TMatcherReturn, TActual> = Matchers<TMatcherReturn, TActual> & {[K in keyof TMatchers]: CustomJestMatcher<TMatchers[K], TMatcherReturn>};
+    type JestExtendedMatchers<TMatchers extends ExpectExtendMap, TActual> = JestMatchersShape<ExtendedMatchers<TMatchers, void, TActual>, ExtendedMatchers<TMatchers, Promise<void>, TActual>>;
+
+    // when have called expect.extend
+    type ExtendedExpectFunction<TMatchers extends ExpectExtendMap> = <TActual>(actual: TActual) => JestExtendedMatchers<TMatchers, TActual>;
+
+    type ExtendedExpect<TMatchers extends ExpectExtendMap>=
+    ExpectProperties &
+    AndNot<CustomAsyncMatchers<TMatchers>> &
+    ExtendedExpectFunction<TMatchers>;
+    /**
+     * Construct a type with the properties of T except for those in type K.
+     */
+    type Omit<T, K extends keyof any> = Pick<T, Exclude<keyof T, K>>;
+    type NonPromiseMatchers<T extends JestMatchersShape> = Omit<T, 'resolves' | 'rejects' | 'not'>;
+    type PromiseMatchers<T extends JestMatchersShape> = Omit<T['resolves'], 'not'>;
+
     interface Constructable {
         new (...args: any[]): any;
     }
diff --git a/types/jest/jest-tests.ts b/types/jest/jest-tests.ts
index bf5eaf9239f8e6..9122ce0f15b9e6 100644
--- a/types/jest/jest-tests.ts
+++ b/types/jest/jest-tests.ts
@@ -580,6 +580,28 @@ switch (mockResult.type) {
         break;
 }
 
+/* getState and setState */
+// $ExpectError
+expect.setState(true);
+expect.setState({for: 'state'});
+const expectState = expect.getState();
+// $ExpectType string
+expectState.currentTestName;
+// $ExpectType string
+expectState.testPath;
+// $ExpectType boolean
+expectState.expand;
+// $ExpectType number
+expectState.assertionCalls;
+// $ExpectType number
+expectState.expectedAssertionsNumber;
+// $ExpectType boolean | undefined
+expectState.isExpectingAssertions;
+// $ExpectType Error[]
+expectState.suppressedErrors;
+// allows additional state properties added by getState
+expectState.for;
+
 /* Snapshot serialization */
 
 const snapshotSerializerPlugin: jest.SnapshotSerializerPlugin = {
@@ -677,39 +699,26 @@ const expectExtendMap: jest.ExpectExtendMap = {};
 expect.extend(expectExtendMap);
 expect.extend({});
 expect.extend({
-    foo(this: jest.MatcherUtils, received: {}, ...actual: Array<{}>) {
+    foo(this: jest.MatcherContext, received: {}, ...actual: Array<{}>) {
         return {
             message: () => JSON.stringify(received),
             pass: false,
         };
     },
 });
+// $ExpectError
+const customMatcherResultMessage: jest.CustomMatcherResult['message'] = 'msg';
 expect.extend({
-    foo(this: jest.MatcherUtils, received: {}, ...actual: Array<{}>) {
-        return {
-            message: JSON.stringify(received),
-            pass: false,
-        };
-    },
-});
-expect.extend({
-    async foo(this: jest.MatcherUtils, received: {}, ...actual: Array<{}>) {
+    async foo(this: jest.MatcherContext, received: {}, ...actual: Array<{}>) {
         return {
             message: () => JSON.stringify(received),
             pass: false,
         };
     },
 });
+
 expect.extend({
-    async foo(this: jest.MatcherUtils, received: {}, ...actual: Array<{}>) {
-        return {
-            message: JSON.stringify(received),
-            pass: false,
-        };
-    },
-});
-expect.extend({
-    foo(this: jest.MatcherUtils) {
+    foo(this: jest.MatcherContext) {
         const isNot: boolean = this.isNot;
         const expand: boolean = this.expand;
 
@@ -760,8 +769,13 @@ expect.extend({
 
         const equals: boolean = this.equals({}, {});
 
+        this.dontThrow();
+        this.fromState;
+        const currentTestName: string = this.currentTestName;
+        const testPath: string = this.testPath;
+
         return {
-            message: () => '',
+            message: () => `Can use ${this.promise} for failure message`,
             pass: false,
         };
     },
@@ -771,6 +785,16 @@ expect.extend({
 
 describe('', () => {
     it('', () => {
+        /* Corrections of previous typings */
+        // $ExpectError
+        expect('').not.not;
+        // $ExpectError
+        expect('').resolves.resolves;
+        // $ExpectType void
+        expect('').toEqual('');
+        // $ExpectType Promise<void>
+        expect(Promise.resolve('')).resolves.toEqual('');
+
         expect(jest.fn()).lastCalledWith();
         expect(jest.fn()).lastCalledWith('jest');
         expect(jest.fn()).lastCalledWith({}, {});
@@ -969,16 +993,11 @@ describe('', () => {
 
         /* Promise matchers */
 
-        expect(Promise.reject('jest')).rejects.toEqual('jest');
-        expect(Promise.reject({})).rejects.toEqual({});
-        expect(Promise.resolve('jest')).rejects.toEqual('jest');
-        expect(Promise.resolve({})).rejects.toEqual({});
-
-        expect(Promise.reject('jest')).resolves.toEqual('jest');
-        expect(Promise.reject({})).resolves.toEqual({});
-        expect(Promise.resolve('jest')).resolves.toEqual('jest');
-        expect(Promise.resolve({})).resolves.toEqual({});
+        expect(Promise.reject('jest')).rejects.toEqual('jest').then(() => {});
+        expect(Promise.reject('jest')).rejects.not.toEqual('other').then(() => {});
 
+        expect(Promise.resolve('jest')).resolves.toEqual('jest').then(() => {});
+        expect(Promise.resolve('jest')).resolves.not.toEqual('other').then(() => {});
         /* type matchers */
 
         expect({}).toBe(expect.anything());
@@ -1020,6 +1039,79 @@ describe('', () => {
     });
 });
 
+/* Custom matchers and CustomExpect */
+describe('', () => {
+    it('', () => {
+        const customMatcher = (expected: any, actual: {prop: string}, option1: boolean) => {
+            return {pass: true, message: () => ''};
+        };
+        const asyncMatcher = () => {
+            return Promise.resolve({pass: true, message: () => ''});
+        };
+
+        const customMatchers = {customMatcher, asyncMatcher};
+        expect.extend(customMatchers);
+        const extendedExpect: jest.ExtendedExpect<typeof customMatchers> = expect as any;
+
+        // extracting matcher types
+        const matchers = extendedExpect({thing: true});
+        let nonPromiseMatchers: jest.NonPromiseMatchers<typeof matchers> = matchers;
+        const isNot = true;
+        if (isNot) {
+            nonPromiseMatchers = matchers.not;
+        }
+        // retains U from <U>(actual: U) => JestExtendedMatchers<T, U>; - BUT CANNOT DO THAT WITH CUSTOM...
+        nonPromiseMatchers.toMatchInlineSnapshot({thing: extendedExpect.any(Boolean)});
+        // $ExpectError
+        nonPromiseMatchers.toMatchInlineSnapshot({notthing: extendedExpect.any(Boolean)});
+
+        let promiseMatchers: jest.PromiseMatchers<typeof matchers> = matchers.rejects;
+        if (isNot) {
+            promiseMatchers = matchers.rejects.not;
+        }
+        // $ExpectType Promise<void>
+        promiseMatchers.customMatcher({prop: ''}, true);
+
+        // retains built in asymmetric matcher
+        extendedExpect.not.arrayContaining;
+
+        extendedExpect.customMatcher({prop: 'good'}, false).asymmetricMatch({}).valueOf();
+        // $ExpectError
+        extendedExpect.customMatcher({prop: {not: 'good'}}, false);
+
+        extendedExpect.not.customMatcher({prop: 'good'}, false).asymmetricMatch({}).valueOf();
+        // $ExpectError
+        extendedExpect.not.customMatcher({prop: 'good'}, 'bad').asymmetricMatch({}).valueOf();
+
+        // $ExpectError
+        const asynMatcherExcluded = extendedExpect.asyncMatcher;
+
+        extendedExpect('').customMatcher({prop: 'good'}, true);
+        // $ExpectError
+        extendedExpect('').customMatcher({prop: 'good'}, 'bad');
+
+        extendedExpect('').not.customMatcher({prop: 'good'}, true);
+        // $ExpectError
+        extendedExpect('').not.customMatcher({prop: 'good'}, 'bad');
+
+        extendedExpect(Promise.resolve('')).resolves.customMatcher({prop: 'good'}, true).then(() => {});
+        // $ExpectError
+        extendedExpect(Promise.resolve('')).resolves.customMatcher({prop: 'good'}, 'bad').then(() => {});
+
+        extendedExpect(Promise.resolve('')).resolves.not.customMatcher({prop: 'good'}, true).then(() => {});
+        // $ExpectError
+        extendedExpect(Promise.resolve('')).resolves.not.customMatcher({prop: 'good'}, 'bad').then(() => {});
+
+        extendedExpect(Promise.reject('')).rejects.customMatcher({prop: 'good'}, true).then(() => {});
+        // $ExpectError
+        extendedExpect(Promise.reject('')).rejects.customMatcher({prop: 'good'}, 'bad').then(() => {});
+
+        extendedExpect(Promise.reject('')).rejects.not.customMatcher({prop: 'good'}, true).then(() => {});
+        // $ExpectError
+        extendedExpect(Promise.reject('')).rejects.not.customMatcher({prop: 'good'}, 'bad').then(() => {});
+    });
+});
+
 /* Test framework and config */
 
 const globalConfig: jest.GlobalConfig = {
diff --git a/types/wordpress__jest-console/index.d.ts b/types/wordpress__jest-console/index.d.ts
index ecda81d6f776ae..247dfcb32f7b54 100644
--- a/types/wordpress__jest-console/index.d.ts
+++ b/types/wordpress__jest-console/index.d.ts
@@ -7,7 +7,7 @@
 /// <reference types="jest" />
 
 declare namespace jest {
-    interface Matchers<R> {
+    interface Matchers<R, T> {
         /**
          * Ensure that `console.error` function was called.
          */