diff --git a/app/_locales/en/messages.json b/app/_locales/en/messages.json
index 50c70cef1..0f5750c04 100644
--- a/app/_locales/en/messages.json
+++ b/app/_locales/en/messages.json
@@ -54,9 +54,21 @@
     "message": "Connect to $1",
     "description": "$1 is the name/origin of a site/dapp that the user can connect to metamask"
   },
+  "connectToAll": {
+    "message": "Connect to all your $1",
+    "description": "$1 will be replaced by the translation of connectToAllAccounts"
+  },
+  "connectToAllAccounts": {
+    "message": "accounts",
+    "description": "will replace $1 in connectToAll, completing the sentence 'connect to all of your accounts', will be text that shows list of accounts on hover"
+  },
   "connectToMultiple": {
-    "message": "Connect to $1 accounts",
-    "description": "$1 is the number of accounts to connect to"
+    "message": "Connect to $1",
+    "description": "$1 will be replaced by the translation of connectToMultipleNumberOfAccounts"
+  },
+  "connectToMultipleNumberOfAccounts": {
+    "message": "$1 accounts",
+    "description": "$1 is the number of accounts to which the site/dapp is asking to connect; this will substitute $1 in connectToMultiple"
   },
   "contractInteraction": {
     "message": "Contract Interaction"
@@ -1025,6 +1037,10 @@
   "personalAddressDetected": {
     "message": "Personal address detected. Input the token contract address."
   },
+  "plusXMore": {
+    "message": "+ $1 more",
+    "description": "$1 is a number of additional but unshown items in a list- this message will be shown in place of those items"
+  },
   "prev": {
     "message": "Prev"
   },
diff --git a/ui/app/components/app/permission-page-container/index.scss b/ui/app/components/app/permission-page-container/index.scss
index 08e7465d8..6daf9774b 100644
--- a/ui/app/components/app/permission-page-container/index.scss
+++ b/ui/app/components/app/permission-page-container/index.scss
@@ -3,7 +3,7 @@
   border: none;
   box-shadow: none;
   margin-top: 45px;
-  width: 466px;
+  width: 488px;
   min-height: 468px;
 
   &__header {
@@ -106,6 +106,15 @@
       padding: 0;
     }
   }
+
+  &__tooltip-body {
+    display: 'flex';
+    flex-direction: 'column';
+  }
+
+  &__bold-title-elements {
+    font-weight: bold;
+  }
 }
 
 .permission-result {
diff --git a/ui/app/components/app/permission-page-container/permission-page-container-content/permission-page-container-content.component.js b/ui/app/components/app/permission-page-container/permission-page-container-content/permission-page-container-content.component.js
index 8360548e9..9b31264a2 100644
--- a/ui/app/components/app/permission-page-container/permission-page-container-content/permission-page-container-content.component.js
+++ b/ui/app/components/app/permission-page-container/permission-page-container-content/permission-page-container-content.component.js
@@ -3,6 +3,7 @@ import React, { PureComponent } from 'react'
 import Identicon from '../../../ui/identicon'
 import IconWithFallBack from '../../../ui/icon-with-fallback'
 import PermissionsConnectHeader from '../../permissions-connect-header'
+import Tooltip from '../../../ui/tooltip-v2'
 import classnames from 'classnames'
 
 export default class PermissionPageContainerContent extends PureComponent {
@@ -13,6 +14,7 @@ export default class PermissionPageContainerContent extends PureComponent {
     permissionsDescriptions: PropTypes.object.isRequired,
     onPermissionToggle: PropTypes.func.isRequired,
     selectedIdentities: PropTypes.array,
+    allIdentitiesSelected: PropTypes.bool,
     redirect: PropTypes.bool,
     permissionRejected: PropTypes.bool,
   }
@@ -21,6 +23,7 @@ export default class PermissionPageContainerContent extends PureComponent {
     redirect: null,
     permissionRejected: null,
     selectedIdentities: [],
+    allIdentitiesSelected: false,
   }
 
   static contextTypes = {
@@ -99,26 +102,92 @@ export default class PermissionPageContainerContent extends PureComponent {
     )
   }
 
-  render () {
-    const { domainMetadata, redirect, permissionRejected, selectedIdentities } = this.props
+  getAccountDescriptor (identity) {
+    return `${identity.label} (...${identity.address.slice(identity.address.length - 4)})`
+  }
+
+  renderAccountTooltip (textContent) {
+    const { selectedIdentities } = this.props
+    const { t } = this.context
+
+    return (
+      <Tooltip
+        key="all-account-connect-tooltip"
+        position="bottom"
+        wrapperClassName="permission-approval-container__bold-title-elements"
+        html={(
+          <div style={{ display: 'flex', flexDirection: 'column' }}>
+            { selectedIdentities.slice(0, 6).map((identity, index) => {
+              return (
+                <div key={ `tooltip-identity-${index}` }>
+                  { this.getAccountDescriptor(identity) }
+                </div>
+              )
+            }) }
+            { selectedIdentities.length > 6
+              ? t('plusXMore', [ selectedIdentities.length - 6 ])
+              : null
+            }
+          </div>
+        )}
+      >
+        { textContent }
+      </Tooltip>
+    )
+  }
+
+  getTitle () {
+    const { domainMetadata, redirect, permissionRejected, selectedIdentities, allIdentitiesSelected } = this.props
     const { t } = this.context
 
-    let titleArgs
     if (redirect && permissionRejected) {
-      titleArgs = [ 'cancelledConnectionWithMetaMask' ]
+      return t('cancelledConnectionWithMetaMask')
     } else if (redirect) {
-      titleArgs = [ 'connectingWithMetaMask' ]
+      return t('connectingWithMetaMask')
     } else if (domainMetadata.extensionId) {
-      titleArgs = [ 'externalExtension', [domainMetadata.extensionId] ]
+      return t('externalExtension', [domainMetadata.extensionId])
+    } else if (allIdentitiesSelected) {
+      return t(
+        'connectToAll',
+        [
+          (
+            <span
+              key="multi-account-connect-all-accounts"
+              className="permission-approval-container__bold-title-elements"
+            >
+              { this.renderAccountTooltip(t('connectToAllAccounts')) }
+            </span>
+          ),
+        ]
+      )
     } else if (selectedIdentities.length > 1) {
-      titleArgs = ['connectToMultiple', [ selectedIdentities.length ] ]
+      return t(
+        'connectToMultiple',
+        [
+          this.renderAccountTooltip(t('connectToMultipleNumberOfAccounts', [ selectedIdentities.length ])),
+        ]
+      )
     } else {
-      titleArgs = [
+      return t(
         'connectTo', [
-          `${selectedIdentities[0].label} (...${selectedIdentities[0].address.slice(selectedIdentities[0].address.length - 4)})`,
-        ],
-      ]
+          (
+            <span
+              key="connect-to-one-account"
+              className="permission-approval-container__bold-title-elements"
+            >
+              { this.getAccountDescriptor(selectedIdentities[0]) }
+            </span>
+          ),
+        ]
+      )
     }
+  }
+
+  render () {
+    const { domainMetadata, redirect } = this.props
+    const { t } = this.context
+
+    const title = this.getTitle()
 
     return (
       <div
@@ -132,7 +201,7 @@ export default class PermissionPageContainerContent extends PureComponent {
               <PermissionsConnectHeader
                 icon={domainMetadata.icon}
                 iconName={domainMetadata.origin}
-                headerTitle={t(...titleArgs)}
+                headerTitle={title}
                 headerText={ domainMetadata.extensionId
                   ? t('thisWillAllowExternalExtension', [domainMetadata.extensionId])
                   : t('thisWillAllow', [domainMetadata.origin])
diff --git a/ui/app/components/app/permission-page-container/permission-page-container.component.js b/ui/app/components/app/permission-page-container/permission-page-container.component.js
index 62ad04940..3f92b3430 100644
--- a/ui/app/components/app/permission-page-container/permission-page-container.component.js
+++ b/ui/app/components/app/permission-page-container/permission-page-container.component.js
@@ -10,6 +10,7 @@ export default class PermissionPageContainer extends Component {
     approvePermissionsRequest: PropTypes.func.isRequired,
     rejectPermissionsRequest: PropTypes.func.isRequired,
     selectedIdentities: PropTypes.array,
+    allIdentitiesSelected: PropTypes.bool,
     permissionsDescriptions: PropTypes.object.isRequired,
     request: PropTypes.object,
     redirect: PropTypes.bool,
@@ -24,6 +25,7 @@ export default class PermissionPageContainer extends Component {
     request: {},
     requestMetadata: {},
     selectedIdentities: [],
+    allIdentitiesSelected: false,
   }
 
   static contextTypes = {
@@ -117,6 +119,7 @@ export default class PermissionPageContainer extends Component {
       selectedIdentities,
       redirect,
       permissionRejected,
+      allIdentitiesSelected,
     } = this.props
 
     return (
@@ -130,6 +133,7 @@ export default class PermissionPageContainer extends Component {
           selectedIdentities={selectedIdentities}
           redirect={redirect}
           permissionRejected={permissionRejected}
+          allIdentitiesSelected={allIdentitiesSelected}
         />
         { !redirect
           ? (
diff --git a/ui/app/components/app/permission-page-container/permission-page-container.container.js b/ui/app/components/app/permission-page-container/permission-page-container.container.js
index ddad61ebf..2c2e5ec53 100644
--- a/ui/app/components/app/permission-page-container/permission-page-container.container.js
+++ b/ui/app/components/app/permission-page-container/permission-page-container.container.js
@@ -3,15 +3,20 @@ import PermissionPageContainer from './permission-page-container.component'
 import {
   getPermissionsDescriptions,
   getTargetDomainMetadata,
+  getMetaMaskIdentities,
 } from '../../../selectors/selectors'
 
 const mapStateToProps = (state, ownProps) => {
-  const { request, cachedOrigin } = ownProps
+  const { request, cachedOrigin, selectedIdentities } = ownProps
   const targetDomainMetadata = getTargetDomainMetadata(state, request, cachedOrigin)
 
+  const allIdentities = getMetaMaskIdentities(state)
+  const allIdentitiesSelected = Object.keys(selectedIdentities).length === Object.keys(allIdentities).length
+
   return {
     permissionsDescriptions: getPermissionsDescriptions(state),
     targetDomainMetadata,
+    allIdentitiesSelected,
   }
 }