diff --git a/ui/src/organizations/actions/orgs.ts b/ui/src/organizations/actions/orgs.ts
index b441c26f4d..219cafe5f3 100644
--- a/ui/src/organizations/actions/orgs.ts
+++ b/ui/src/organizations/actions/orgs.ts
@@ -2,6 +2,7 @@
 import {Dispatch} from 'redux'
 import {ThunkAction} from 'redux-thunk'
 import {push, RouterAction} from 'react-router-redux'
+import HoneyBadger from 'honeybadger-js'
 
 // APIs
 import {getErrorMessage} from 'src/utils/api'
@@ -80,6 +81,9 @@ export interface SetOrg {
 }
 
 export const setOrg = (org: Organization): SetOrg => {
+  HoneyBadger.setContext({
+    orgID: org.id,
+  })
   return {
     type: ActionTypes.SetOrg,
     payload: {org},
diff --git a/ui/src/shared/actions/me.ts b/ui/src/shared/actions/me.ts
index 608f4a7cb6..96e661214a 100644
--- a/ui/src/shared/actions/me.ts
+++ b/ui/src/shared/actions/me.ts
@@ -1,5 +1,6 @@
 import {MeState} from 'src/shared/reducers/me'
 import {client} from 'src/utils/api'
+import HoneyBadger from 'honeybadger-js'
 
 export enum ActionTypes {
   SetMe = 'SET_ME',
@@ -25,8 +26,12 @@ export const getMe = () => async dispatch => {
   try {
     const user = await client.users.me()
 
+    HoneyBadger.setContext({
+      user_id: user.id,
+    })
+
     dispatch(setMe(user))
-  } catch (e) {
-    console.error(e)
+  } catch (error) {
+    console.error(error)
   }
 }
diff --git a/ui/src/shared/utils/errors.ts b/ui/src/shared/utils/errors.ts
index 580fc37636..02d39d92b8 100644
--- a/ui/src/shared/utils/errors.ts
+++ b/ui/src/shared/utils/errors.ts
@@ -2,6 +2,8 @@ import {ErrorInfo} from 'react'
 import HoneyBadger from 'honeybadger-js'
 import {CLOUD, GIT_SHA} from 'src/shared/constants'
 
+import {getUserFlags} from 'src/shared/utils/featureFlag'
+
 if (CLOUD) {
   HoneyBadger.configure({
     apiKey: process.env.HONEYBADGER_KEY,
@@ -10,18 +12,44 @@ if (CLOUD) {
   })
 }
 
-interface AdditionalOptions {
+// See https://docs.honeybadger.io/lib/javascript/guides/reporting-errors.html#additional-options
+interface HoneyBadgerAdditionalOptions {
   component?: string
   context?: {[key: string]: any}
+  cookies?: {[key: string]: any}
   name?: string
+  params?: {[key: string]: any}
 }
 
 export const reportError = (
   error: Error,
-  additionalOptions?: AdditionalOptions
+  additionalOptions?: HoneyBadgerAdditionalOptions
 ): void => {
+  let additionalContext = {}
+  if (additionalOptions && additionalOptions.context) {
+    additionalContext = {...additionalOptions.context}
+  }
+
+  const context = {
+    ...additionalContext,
+    ...getUserFlags(),
+  }
+
+  let options: HoneyBadgerAdditionalOptions = {}
+  if (additionalOptions) {
+    options = {...additionalOptions}
+
+    delete options.context // already included in the above context object
+  }
+
   if (CLOUD) {
-    HoneyBadger.notify(error, additionalOptions)
+    HoneyBadger.notify(error, {context, ...options})
+  } else {
+    const honeyBadgerContext = (HoneyBadger as any).context
+    /* eslint-disable no-console */
+    console.log('Context that would have been sent to HoneyBadger:')
+    console.table({...honeyBadgerContext, ...context, ...options})
+    /* eslint-enable no-console */
   }
 }