diff --git a/docs/docs/env-vars.md b/docs/docs/env-vars.md
index 1b49ea55..58561f6c 100644
--- a/docs/docs/env-vars.md
+++ b/docs/docs/env-vars.md
@@ -18,6 +18,8 @@ CodeRoad has a number of configurations:
 
 - `CODEROAD_CONTENT_SECURITY_POLICY_EXEMPTIONS` - a list of CSP exemption hashes. For multiples, separate the list with a space.
 
+- `CODEROAD_WEBHOOK_TOKEN` - an optional token for authenticating/authorizing webhook endpoints. Passed to the webhook endpoint in a `CodeRoad-User-Token` header.
+
 ## How to Use Variables
 
 ### Local
diff --git a/src/actions/onRunReset.ts b/src/actions/onRunReset.ts
index 890b084e..4ae140a2 100644
--- a/src/actions/onRunReset.ts
+++ b/src/actions/onRunReset.ts
@@ -32,7 +32,10 @@ const onRunReset = async (action: ResetAction, context: Context): Promise<void>
   // if tutorial.config.reset.command, run it
   const resetActions = tutorial?.config?.reset
   if (resetActions) {
-    hooks.onReset({ commands: resetActions?.commands, vscodeCommands: resetActions?.vscodeCommands })
+    hooks.onReset(
+      { commands: resetActions?.commands, vscodeCommands: resetActions?.vscodeCommands },
+      tutorial?.id as string,
+    )
   }
 }
 
diff --git a/src/actions/onTutorialConfigContinue.ts b/src/actions/onTutorialConfigContinue.ts
index 397e96ad..f5e173b0 100644
--- a/src/actions/onTutorialConfigContinue.ts
+++ b/src/actions/onTutorialConfigContinue.ts
@@ -5,6 +5,7 @@ import Context from '../services/context/context'
 import tutorialConfig from './utils/tutorialConfig'
 import { COMMANDS, send } from '../commands'
 import logger from '../services/logger'
+import { setupWebhook } from '../services/hooks/webhooks'
 
 const onTutorialConfigContinue = async (action: T.Action, context: Context): Promise<void> => {
   logger('onTutorialConfigContinue', action)
@@ -19,6 +20,11 @@ const onTutorialConfigContinue = async (action: T.Action, context: Context): Pro
       data: tutorialToContinue,
       alreadyConfigured: true,
     })
+
+    // configure webhook
+    if (tutorialToContinue.config?.webhook) {
+      setupWebhook(tutorialToContinue.config.webhook)
+    }
   } catch (e) {
     const error = {
       type: 'UnknownError',
diff --git a/src/actions/onTutorialConfigNew.ts b/src/actions/onTutorialConfigNew.ts
index 5c2774ac..171bee1a 100644
--- a/src/actions/onTutorialConfigNew.ts
+++ b/src/actions/onTutorialConfigNew.ts
@@ -8,6 +8,7 @@ import { version, compareVersions } from '../services/dependencies'
 import Context from '../services/context/context'
 import tutorialConfig from './utils/tutorialConfig'
 import { send } from '../commands'
+import { setupWebhook } from '../services/hooks/webhooks'
 
 const onTutorialConfigNew = async (action: T.Action, context: Context): Promise<void> => {
   try {
@@ -108,6 +109,11 @@ const onTutorialConfigNew = async (action: T.Action, context: Context): Promise<
       return
     }
 
+    // configure webhook
+    if (data.config?.webhook) {
+      setupWebhook(data.config.webhook)
+    }
+
     // report back to the webview that setup is complete
     send({ type: 'TUTORIAL_CONFIGURED' })
   } catch (e) {
diff --git a/src/commands.ts b/src/commands.ts
index c7ba69a5..5eaaeab2 100644
--- a/src/commands.ts
+++ b/src/commands.ts
@@ -65,7 +65,7 @@ export const createCommands = ({ extensionPath, workspaceState }: CreateCommandP
       if (!alreadyConfigured) {
         const setupActions = data.config.setup
         if (setupActions) {
-          hooks.onInit(setupActions)
+          hooks.onInit(setupActions, data.id)
         }
       }
       testRunner = createTestRunner(data, {
diff --git a/src/environment.ts b/src/environment.ts
index 8b7f5f3f..59077d61 100644
--- a/src/environment.ts
+++ b/src/environment.ts
@@ -43,3 +43,6 @@ export const DISABLE_RUN_ON_SAVE = (process.env.CODEROAD_DISABLE_RUN_ON_SAVE ||
 // for multiple exemptions, separate each with a space "a1 b1"
 export const CONTENT_SECURITY_POLICY_EXEMPTIONS: string | null =
   process.env.CODEROAD_CONTENT_SECURITY_POLICY_EXEMPTIONS || null
+
+// optional token for authorization/authentication of webhook calls
+export const WEBHOOK_TOKEN = process.env.CODEROAD_WEBHOOK_TOKEN || null
diff --git a/src/services/hooks/index.ts b/src/services/hooks/index.ts
index ddcc7757..309d3ae3 100644
--- a/src/services/hooks/index.ts
+++ b/src/services/hooks/index.ts
@@ -7,14 +7,18 @@ import runCommands from './utils/runCommands'
 import runVSCodeCommands from './utils/runVSCodeCommands'
 import * as telemetry from '../telemetry'
 import { runTest } from '../../actions/onTest'
-import logger from '../logger'
 import { VERSION } from '../../environment'
+import * as webhooks from './webhooks'
 
 // run at the end of when a tutorial is configured
-export const onInit = async (actions: TT.StepActions): Promise<void> => {
+export const onInit = async (actions: TT.StepActions, tutorialId: string): Promise<void> => {
   await loadCommits(actions?.commits)
   await runCommands(actions?.commands)
   await runVSCodeCommands(actions?.vscodeCommands)
+  webhooks.onInit({
+    tutorialId,
+    coderoadVersion: VERSION,
+  })
 }
 
 // run when a level starts
@@ -43,10 +47,13 @@ export const onSolutionEnter = async (actions: TT.StepActions): Promise<void> =>
 }
 
 // run when "reset" is triggered
-export const onReset = async (actions: TT.StepActions): Promise<void> => {
+export const onReset = async (actions: TT.StepActions, tutorialId: string): Promise<void> => {
   await resetWatchers()
   await runCommands(actions?.commands)
   await runVSCodeCommands(actions?.vscodeCommands)
+  webhooks.onReset({
+    tutorialId,
+  })
 }
 
 // run when an uncaught exception is thrown
@@ -66,6 +73,11 @@ export const onStepComplete = async ({
 }): Promise<void> => {
   git.saveCommit(`Save progress: ${stepId}`)
   telemetry.onEvent('step_complete', { tutorialId, stepId, levelId, version: VERSION })
+  webhooks.onStepComplete({
+    tutorialId,
+    levelId,
+    stepId,
+  })
 }
 
 // run when a level is complete (all tasks pass or no tasks)
@@ -77,9 +89,16 @@ export const onLevelComplete = async ({
   levelId: string
 }): Promise<void> => {
   telemetry.onEvent('level_complete', { tutorialId, levelId, version: VERSION })
+  webhooks.onLevelComplete({
+    tutorialId,
+    levelId,
+  })
 }
 
 // run when all levels are complete
 export const onTutorialComplete = async ({ tutorialId }: { tutorialId: string }): Promise<void> => {
   telemetry.onEvent('tutorial_complete', { tutorialId, version: VERSION })
+  webhooks.onTutorialComplete({
+    tutorialId,
+  })
 }
diff --git a/src/services/hooks/webhooks.ts b/src/services/hooks/webhooks.ts
new file mode 100644
index 00000000..a245d4cb
--- /dev/null
+++ b/src/services/hooks/webhooks.ts
@@ -0,0 +1,101 @@
+import * as TT from 'typings/tutorial'
+import fetch from 'node-fetch'
+import logger from '../logger'
+import { WEBHOOK_TOKEN } from '../../environment'
+
+const WEBHOOK_EVENTS = {
+  init: false,
+  reset: false,
+  step_complete: false,
+  level_complete: false,
+  tutorial_complete: false,
+}
+
+// varaibles set on init
+let WEBHOOK_URI: string | undefined
+
+export const setupWebhook = (webhookConfig: TT.WebhookConfig) => {
+  if (!webhookConfig.url) {
+    return
+  }
+  // set webhook uri
+  WEBHOOK_URI = webhookConfig.url
+
+  // set webhook event triggers
+  const events = webhookConfig.events as TT.WebhookConfigEvents
+  for (const eventName of Object.keys(events || {})) {
+    WEBHOOK_EVENTS[eventName] = events[eventName]
+  }
+}
+
+const callWebhookEndpoint = async <B>(bodyObject: B): Promise<void> => {
+  if (!WEBHOOK_URI) {
+    return
+  }
+
+  const headers = { 'Content-Type': 'application/json' }
+  // if the webhook token is specified as env var, sends a token with the request
+  if (WEBHOOK_TOKEN) {
+    headers['CodeRoad-User-Token'] = WEBHOOK_TOKEN
+  }
+
+  const body = JSON.stringify(bodyObject)
+
+  try {
+    const sendEvent = await fetch(WEBHOOK_URI, {
+      method: 'POST',
+      headers,
+      body,
+    })
+    if (!sendEvent.ok) {
+      throw new Error('Error sending event')
+    }
+  } catch (err: unknown) {
+    logger(`Failed to call webhook endpoint ${WEBHOOK_URI} with body ${body}`)
+  }
+}
+
+type WebhookEventInit = {
+  tutorialId: string
+  coderoadVersion: string
+}
+
+export const onInit = (event: WebhookEventInit): void => {
+  if (WEBHOOK_EVENTS.init) {
+    callWebhookEndpoint<WebhookEventInit>(event)
+  }
+}
+
+type WebhookEventReset = {
+  tutorialId: string
+}
+
+export const onReset = (event: WebhookEventReset): void => {
+  if (WEBHOOK_EVENTS.reset) {
+    callWebhookEndpoint<WebhookEventReset>(event)
+  }
+}
+
+type WebhookEventStepComplete = { tutorialId: string; version: string; levelId: string; stepId: string }
+
+export const onStepComplete = (event: WebhookEventStepComplete): void => {
+  if (WEBHOOK_EVENTS.step_complete) {
+    callWebhookEndpoint<WebhookEventStepComplete>(event)
+  }
+}
+
+type WebhookEventLevelComplete = { tutorialId: string; version: string; levelId: string }
+
+export const onLevelComplete = (event: WebhookEventLevelComplete): void => {
+  if (WEBHOOK_EVENTS.level_complete) {
+    callWebhookEndpoint<WebhookEventLevelComplete>(event)
+  }
+}
+
+type WebhookEevntTutorialComplete = { tutorialId: string; version: string }
+
+export const onTutorialComplete = (event: WebhookEevntTutorialComplete): void => {
+  if (WEBHOOK_EVENTS.tutorial_complete) {
+    callWebhookEndpoint<WebhookEevntTutorialComplete>(event)
+  }
+}
diff --git a/typings/tutorial.d.ts b/typings/tutorial.d.ts
index 3f45e558..3a32599a 100644
--- a/typings/tutorial.d.ts
+++ b/typings/tutorial.d.ts
@@ -14,6 +14,7 @@ export type TutorialConfig = {
   dependencies?: TutorialDependency[]
   setup?: StepActions
   reset?: ConfigReset
+  webhook?: WebhookConfig
 }
 
 /** Logical groupings of tasks */
@@ -92,3 +93,15 @@ export interface TutorialAppVersions {
 }
 
 export type VSCodeCommand = string | [string, any]
+
+export interface WebhookConfigEvents {
+  init?: boolean
+  reset?: boolean
+  step_complete?: boolean
+  level_complete?: boolean
+  tutorial_complete?: boolean
+}
+export interface WebhookConfig {
+  url: string
+  events?: WebhookConfigEvents
+}