diff --git a/packages/github/README.md b/packages/github/README.md
index 12c5b0b078..ba8224ac2f 100644
--- a/packages/github/README.md
+++ b/packages/github/README.md
@@ -55,3 +55,31 @@ const newIssue = await octokit.issues.create({
   body: 'Hello Universe!'
 });
 ```
+
+### Context Payload Casting in Typescript
+The [GitHub Webhook Event](https://developer.github.com/webhooks/#events) payload is provided as a part of the context. Based on the type of event that [triggered your workflow](https://help.github.com/en/actions/automating-your-workflow-with-github-actions/events-that-trigger-workflows), the structure of that object may change. You can cast this field to access these members in a type safe way.
+
+```ts
+import * as core from '@actions/core'
+import * as github from '@actions/github'
+import * as Webhooks from '@octokit/webhooks'
+
+const payload = github.context.payload
+if (github.context.eventName === 'push') {
+  const pushPayload = github.context.payload as Webhooks.WebhookPayloadPush
+  core.info(`The head commit is: ${pushPayload.head_commit}`)
+}
+```
+
+There may be cases where multiple events have a field you need. For example, we can get the issue number field from the `issue` event and the `issue_comment` event
+```ts
+import * as core from '@actions/core'
+import * as github from '@actions/github'
+import * as Webhooks from '@octokit/webhooks'
+
+const payload = github.context.payload
+if (payload && 'pull_request' in payload) {
+  core.info(`The issue is: ${JSON.stringify(payload.pull_request.number)}`)
+}
+```
+
diff --git a/packages/github/__tests__/lib.test.ts b/packages/github/__tests__/lib.test.ts
index 5c042f2a8c..459317eaee 100644
--- a/packages/github/__tests__/lib.test.ts
+++ b/packages/github/__tests__/lib.test.ts
@@ -1,8 +1,13 @@
 import * as path from 'path'
 import {Context} from '../src/context'
+import {PayloadRepository} from '@octokit/webhooks'
+import {WebhookPayload} from '../src/interfaces'
 
 /* eslint-disable @typescript-eslint/no-require-imports */
 
+// TODO: https://github.com/actions/toolkit/issues/291, ESLint chokes on the a?.b syntax introduced in Typescript 3.7
+/* eslint-disable @typescript-eslint/no-object-literal-type-assertion */
+
 describe('@actions/context', () => {
   let context: Context
 
@@ -16,11 +21,18 @@ describe('@actions/context', () => {
     expect(context.payload).toEqual(require('./payload.json'))
   })
 
-  it('returns an empty payload if the GITHUB_EVENT_PATH environment variable is falsey', () => {
+  it('returns an undefined payload if the GITHUB_EVENT_PATH environment variable is falsey', () => {
     delete process.env.GITHUB_EVENT_PATH
 
     context = new Context()
-    expect(context.payload).toEqual({})
+    expect(context.payload).toEqual(undefined)
+  })
+
+  it('returns an undefined payload if the GITHUB_EVENT_PATH environment variable does not point to a file', () => {
+    process.env.GITHUB_EVENT_PATH = path.join(__dirname, 'invalidfile.json')
+
+    context = new Context()
+    expect(context.payload).toEqual(undefined)
   })
 
   it('returns attributes from the GITHUB_REPOSITORY', () => {
@@ -29,18 +41,13 @@ describe('@actions/context', () => {
 
   it('returns attributes from the repository payload', () => {
     delete process.env.GITHUB_REPOSITORY
-
-    context.payload.repository = {
-      name: 'test',
-      owner: {login: 'user'}
-    }
     expect(context.repo).toEqual({owner: 'user', repo: 'test'})
   })
 
   it("return error for context.repo when repository doesn't exist", () => {
     delete process.env.GITHUB_REPOSITORY
-
-    context.payload.repository = undefined
+    delete process.env.GITHUB_EVENT_PATH
+    context = new Context()
     expect(() => context.repo).toThrowErrorMatchingSnapshot()
   })
 
@@ -55,9 +62,10 @@ describe('@actions/context', () => {
   it('works with pullRequest payloads', () => {
     delete process.env.GITHUB_REPOSITORY
     context.payload = {
-      pullRequest: {number: 2},
-      repository: {owner: {login: 'user'}, name: 'test'}
-    }
+      // eslint-disable-next-line @typescript-eslint/camelcase
+      pull_request: {number: 2},
+      repository: {owner: {login: 'user'}, name: 'test'} as PayloadRepository
+    } as WebhookPayload
     expect(context.issue).toEqual({
       number: 2,
       owner: 'user',
@@ -69,8 +77,8 @@ describe('@actions/context', () => {
     delete process.env.GITHUB_REPOSITORY
     context.payload = {
       number: 2,
-      repository: {owner: {login: 'user'}, name: 'test'}
-    }
+      repository: {owner: {login: 'user'}, name: 'test'} as PayloadRepository
+    } as WebhookPayload
     expect(context.issue).toEqual({
       number: 2,
       owner: 'user',
diff --git a/packages/github/package-lock.json b/packages/github/package-lock.json
index 6dcc35ef9f..d891b320e2 100644
--- a/packages/github/package-lock.json
+++ b/packages/github/package-lock.json
@@ -524,6 +524,29 @@
         "@types/node": ">= 8"
       }
     },
+    "@octokit/webhooks": {
+      "version": "7.0.0",
+      "resolved": "https://registry.npmjs.org/@octokit/webhooks/-/webhooks-7.0.0.tgz",
+      "integrity": "sha512-oSZuKc2LDNtt3vW7Iq9XNvIm3i6CxMkrzkuyHinR6IjVRb7EuiMshn3AVDdXdDtAVHvxwxj3ikt3jsTlFE6zEA==",
+      "requires": {
+        "debug": "^4.0.0"
+      },
+      "dependencies": {
+        "debug": {
+          "version": "4.1.1",
+          "resolved": "https://registry.npmjs.org/debug/-/debug-4.1.1.tgz",
+          "integrity": "sha512-pYAIzeRo8J6KPEaJ0VWOh5Pzkbw/RetuzehGM7QRRX5he4fPHx2rdKMB256ehJCkX+XRQm16eZLqLNS8RSZXZw==",
+          "requires": {
+            "ms": "^2.1.1"
+          }
+        },
+        "ms": {
+          "version": "2.1.2",
+          "resolved": "https://registry.npmjs.org/ms/-/ms-2.1.2.tgz",
+          "integrity": "sha512-sGkPx+VjMtmA6MX27oA4FBFELFCZZ4S4XqeGOXCv68tT+jb3vk/RyaKWP0PTKyWtmLSM0b+adUTEvbs1PEaH2w=="
+        }
+      }
+    },
     "@types/babel__core": {
       "version": "7.1.2",
       "resolved": "https://registry.npmjs.org/@types/babel__core/-/babel__core-7.1.2.tgz",
diff --git a/packages/github/package.json b/packages/github/package.json
index b956d42363..6d3ccbdf56 100644
--- a/packages/github/package.json
+++ b/packages/github/package.json
@@ -38,7 +38,8 @@
   },
   "dependencies": {
     "@octokit/graphql": "^4.3.1",
-    "@octokit/rest": "^16.15.0"
+    "@octokit/rest": "^16.15.0",
+    "@octokit/webhooks": "^7.0.0"
   },
   "devDependencies": {
     "jest": "^24.7.1"
diff --git a/packages/github/src/context.ts b/packages/github/src/context.ts
index f2aafde112..3884244954 100644
--- a/packages/github/src/context.ts
+++ b/packages/github/src/context.ts
@@ -7,7 +7,7 @@ export class Context {
   /**
    * Webhook payload object that triggered the workflow
    */
-  payload: WebhookPayload
+  payload?: WebhookPayload
 
   eventName: string
   sha: string
@@ -20,7 +20,6 @@ export class Context {
    * Hydrate the context from the environment
    */
   constructor() {
-    this.payload = {}
     if (process.env.GITHUB_EVENT_PATH) {
       if (existsSync(process.env.GITHUB_EVENT_PATH)) {
         this.payload = JSON.parse(
@@ -40,11 +39,12 @@ export class Context {
   }
 
   get issue(): {owner: string; repo: string; number: number} {
-    const payload = this.payload
-
+    // TODO: https://github.com/actions/toolkit/issues/291 to remove no-unnecessary-type-assertion
+    // eslint-disable-next-line @typescript-eslint/no-explicit-any, @typescript-eslint/no-unnecessary-type-assertion
+    const payload = this.payload as any
     return {
       ...this.repo,
-      number: (payload.issue || payload.pullRequest || payload).number
+      number: (payload.issue || payload.pull_request || payload).number
     }
   }
 
@@ -54,10 +54,10 @@ export class Context {
       return {owner, repo}
     }
 
-    if (this.payload.repository) {
+    if (this.payload?.repository) {
       return {
-        owner: this.payload.repository.owner.login,
-        repo: this.payload.repository.name
+        owner: this.payload?.repository.owner.login,
+        repo: this.payload?.repository.name
       }
     }
 
diff --git a/packages/github/src/interfaces.ts b/packages/github/src/interfaces.ts
index c20aadd827..7f2f367eb3 100644
--- a/packages/github/src/interfaces.ts
+++ b/packages/github/src/interfaces.ts
@@ -1,39 +1,25 @@
-/* eslint-disable @typescript-eslint/no-explicit-any */
-
-export interface PayloadRepository {
-  [key: string]: any
-  full_name?: string
-  name: string
-  owner: {
-    [key: string]: any
-    login: string
-    name?: string
-  }
-  html_url?: string
-}
-
-export interface WebhookPayload {
-  [key: string]: any
-  repository?: PayloadRepository
-  issue?: {
-    [key: string]: any
-    number: number
-    html_url?: string
-    body?: string
-  }
-  pull_request?: {
-    [key: string]: any
-    number: number
-    html_url?: string
-    body?: string
-  }
-  sender?: {
-    [key: string]: any
-    type: string
-  }
-  action?: string
-  installation?: {
-    id: number
-    [key: string]: any
-  }
-}
+import Webhooks from '@octokit/webhooks'
+export type WebhookPayload =
+  | Webhooks.WebhookPayloadPush
+  | Webhooks.WebhookPayloadPullRequest
+  | Webhooks.WebhookPayloadPullRequestReview
+  | Webhooks.WebhookPayloadPullRequestReviewComment
+  | Webhooks.WebhookPayloadStatus
+  | Webhooks.WebhookPayloadIssues
+  | Webhooks.WebhookPayloadIssueComment
+  | Webhooks.WebhookPayloadRelease
+  | Webhooks.WebhookPayloadRepositoryDispatch
+  | Webhooks.WebhookPayloadCheckRun
+  | Webhooks.WebhookPayloadDeployment
+  | Webhooks.WebhookPayloadCheckSuite
+  | Webhooks.WebhookPayloadWatch
+  | Webhooks.WebhookPayloadDeploymentStatus
+  | Webhooks.WebhookPayloadCreate
+  | Webhooks.WebhookPayloadDelete
+  | Webhooks.WebhookPayloadProjectCard
+  | Webhooks.WebhookPayloadPageBuild
+  | Webhooks.WebhookPayloadFork
+  | Webhooks.WebhookPayloadGollum
+  | Webhooks.WebhookPayloadMilestone
+  | Webhooks.WebhookPayloadProject
+  | Webhooks.WebhookPayloadLabel