diff --git a/apps/console/app/routes/apps/$clientId/team.tsx b/apps/console/app/routes/apps/$clientId/team.tsx
index 57aef6a56c..cd17da8407 100644
--- a/apps/console/app/routes/apps/$clientId/team.tsx
+++ b/apps/console/app/routes/apps/$clientId/team.tsx
@@ -128,7 +128,7 @@ export const action: ActionFunction = getRollupReqFunctionErrorWrapper(
 )
 
 export default () => {
-  useConnectResult(['SUCCESS', 'ALREADY_CONNECTED', 'CANCEL'])
+  useConnectResult()
 
   const submit = useSubmit()
 
diff --git a/apps/passport/app/routes/authorize.tsx b/apps/passport/app/routes/authorize.tsx
index 357e88b571..a0bcc768c6 100644
--- a/apps/passport/app/routes/authorize.tsx
+++ b/apps/passport/app/routes/authorize.tsx
@@ -28,7 +28,6 @@ import {
 } from '~/utils/authorize.server'
 import { useEffect, useState } from 'react'
 import { BadRequestError, InternalServerError } from '@proofzero/errors'
-import { JsonError } from '@proofzero/utils/errors'
 import { AuthorizationControlSelection } from '@proofzero/types/application'
 import useConnectResult from '@proofzero/design-system/src/hooks/useConnectResult'
 
@@ -418,7 +417,7 @@ export default function Authorize() {
   const navigate = useNavigate()
   const transition = useTransition()
 
-  useConnectResult(['ALREADY_CONNECTED', 'CANCEL'])
+  useConnectResult()
 
   const cancelCallback = () => {
     const redirectURL = new URL(redirectUri)
diff --git a/apps/passport/app/routes/connect/$address/sign.tsx b/apps/passport/app/routes/connect/$address/sign.tsx
index 43ba878887..e07d6869be 100644
--- a/apps/passport/app/routes/connect/$address/sign.tsx
+++ b/apps/passport/app/routes/connect/$address/sign.tsx
@@ -8,9 +8,10 @@ import { CryptoAddressType, NodeType } from '@proofzero/types/address'
 import { getAuthzCookieParams, getUserSession } from '../../../session.server'
 import { getAuthzRedirectURL } from '../../../utils/authenticate.server'
 
-import { signMessageTemplate } from '@proofzero/packages/utils'
+import { parseJwt, signMessageTemplate } from '@proofzero/packages/utils'
 import { BadRequestError } from '@proofzero/errors'
 import { getRollupReqFunctionErrorWrapper } from '@proofzero/utils/errors'
+import type { AccountURN } from '@proofzero/urns/account'
 
 export const loader: LoaderFunction = getRollupReqFunctionErrorWrapper(
   async ({ request, context, params }) => {
@@ -49,6 +50,7 @@ export const loader: LoaderFunction = getRollupReqFunctionErrorWrapper(
 export const action: ActionFunction = getRollupReqFunctionErrorWrapper(
   async ({ request, context, params }) => {
     const appData = await getAuthzCookieParams(request, context.env)
+    const jwt = await getUserSession(request, context.env, params.clientId)
 
     const { address } = params
     if (!address)
@@ -74,8 +76,15 @@ export const action: ActionFunction = getRollupReqFunctionErrorWrapper(
       forceAccountCreation: !appData || appData.rollup_action !== 'connect',
     })
 
+    const accountURNFromAddress = await addressClient.getAccount.query()
+
+
     if (appData?.rollup_action === 'connect' && existing) {
-      return redirect(getAuthzRedirectURL(appData, 'ALREADY_CONNECTED'))
+      const accountURN = parseJwt(jwt).sub! as AccountURN
+      if (accountURN === accountURNFromAddress) {
+        return redirect(getAuthzRedirectURL(appData, 'ALREADY_CONNECTED_ERROR'))
+      }
+      return redirect(getAuthzRedirectURL(appData, 'ACCOUNT_CONNECT_ERROR'))
     }
 
     // TODO: handle the error case
diff --git a/apps/passport/app/utils/authenticate.server.ts b/apps/passport/app/utils/authenticate.server.ts
index 3172c4c394..053a66dc86 100644
--- a/apps/passport/app/utils/authenticate.server.ts
+++ b/apps/passport/app/utils/authenticate.server.ts
@@ -2,7 +2,6 @@ import { AddressURNSpace } from '@proofzero/urns/address'
 import type { AddressURN } from '@proofzero/urns/address'
 import type { AccountURN } from '@proofzero/urns/account'
 
-import { JsonError } from '@proofzero/utils/errors'
 import { GrantType, ResponseType } from '@proofzero/types/access'
 
 import {
@@ -13,6 +12,7 @@ import {
 import {
   createUserSession,
   getAuthzCookieParamsSession,
+  getUserSession,
   parseJwt,
 } from '~/session.server'
 import { generateGradient } from './gradient.server'
@@ -40,15 +40,25 @@ export const authenticateAddress = async (
     })
   }
 
+  const jwt = await getUserSession(request, env, appData?.clientId)
   if (
     appData.rollup_action &&
     ['connect', 'reconnect'].includes(appData?.rollup_action)
   ) {
+    let result = undefined
+
+    if (existing && appData.rollup_action === 'connect') {
+      const loggedInAccount = parseJwt(jwt).sub
+      if (account !== loggedInAccount) {
+        result = 'ACCOUNT_CONNECT_ERROR'
+      } else {
+        result = 'ALREADY_CONNECTED_ERROR'
+      }
+    }
+
     const redirectURL = getAuthzRedirectURL(
       appData,
-      existing && appData.rollup_action === 'connect'
-        ? 'ALREADY_CONNECTED'
-        : undefined
+      result
     )
 
     return redirect(redirectURL)
diff --git a/packages/design-system/src/hooks/useConnectResult.tsx b/packages/design-system/src/hooks/useConnectResult.tsx
index 21321a692e..2318f5536d 100644
--- a/packages/design-system/src/hooks/useConnectResult.tsx
+++ b/packages/design-system/src/hooks/useConnectResult.tsx
@@ -2,7 +2,12 @@ import { ToastType, toast } from '../atoms/toast'
 import { useEffect } from 'react'
 
 export default (
-  handledMessageTypes: string[] = ['SUCCESS', 'ALREADY_CONNECTED', 'CANCEL']
+  handledMessageTypes: string[] = [
+    'SUCCESS',
+    'ACCOUNT_CONNECT_ERROR',
+    'ALREADY_CONNECTED_ERROR',
+    'CANCEL'
+  ]
 ) => {
   useEffect(() => {
     const url = new URL(window.location.href)
@@ -18,10 +23,21 @@ export default (
               { duration: 2000 }
             )
             break
-          case 'ALREADY_CONNECTED':
+          case 'ACCOUNT_CONNECT_ERROR':
             toast(
               ToastType.Error,
-              { message: 'Account already connected' },
+              {
+                message: 'Could not connect this account to your identity.\
+               It may be connected to another identity.' },
+              { duration: 2000 }
+            )
+            break
+          case 'ALREADY_CONNECTED_ERROR':
+            toast(
+              ToastType.Error,
+              {
+                message: 'Account is already connected to your identity.'
+              },
               { duration: 2000 }
             )
             break