diff --git a/app/_locales/en/messages.json b/app/_locales/en/messages.json
index ab52fa49c..dee684716 100644
--- a/app/_locales/en/messages.json
+++ b/app/_locales/en/messages.json
@@ -1255,6 +1255,9 @@
   "ledgerAccountRestriction": {
     "message": "You need to make use your last account before you can add a new one."
   },
+  "ledgerConnectionInstructionCloseOtherApps": {
+    "message": "Close any other software connected to your device and then click here to refresh."
+  },
   "ledgerConnectionInstructionHeader": {
     "message": "Prior to clicking confirm:"
   },
diff --git a/app/scripts/metamask-controller.js b/app/scripts/metamask-controller.js
index 2010ce69f..40832c0bc 100644
--- a/app/scripts/metamask-controller.js
+++ b/app/scripts/metamask-controller.js
@@ -845,6 +845,10 @@ export default class MetamaskController extends EventEmitter {
         this.setLedgerTransportPreference,
         this,
       ),
+      attemptLedgerTransportCreation: nodeify(
+        this.attemptLedgerTransportCreation,
+        this,
+      ),
 
       // mobile
       fetchInfoToSync: nodeify(this.fetchInfoToSync, this),
@@ -1556,6 +1560,11 @@ export default class MetamaskController extends EventEmitter {
     return keyring;
   }
 
+  async attemptLedgerTransportCreation() {
+    const keyring = await this.getKeyringForDevice('ledger');
+    return await keyring.attemptMakeApp();
+  }
+
   /**
    * Fetch account list from a trezor device.
    *
diff --git a/package.json b/package.json
index c5789c618..b991a755c 100644
--- a/package.json
+++ b/package.json
@@ -105,7 +105,7 @@
     "@material-ui/core": "^4.11.0",
     "@metamask/contract-metadata": "^1.28.0",
     "@metamask/controllers": "^17.0.0",
-    "@metamask/eth-ledger-bridge-keyring": "^0.9.0",
+    "@metamask/eth-ledger-bridge-keyring": "^0.10.0",
     "@metamask/eth-token-tracker": "^3.0.1",
     "@metamask/etherscan-link": "^2.1.0",
     "@metamask/jazzicon": "^2.0.0",
diff --git a/shared/constants/hardware-wallets.js b/shared/constants/hardware-wallets.js
index e780555fc..705754fe7 100644
--- a/shared/constants/hardware-wallets.js
+++ b/shared/constants/hardware-wallets.js
@@ -24,3 +24,10 @@ export const WEBHID_CONNECTED_STATUSES = {
   NOT_CONNECTED: 'notConnected',
   UNKNOWN: 'unknown',
 };
+
+export const TRANSPORT_STATES = {
+  NONE: 'NONE',
+  VERIFIED: 'VERIFIED',
+  DEVICE_OPEN_FAILURE: 'DEVICE_OPEN_FAILURE',
+  UNKNOWN_FAILURE: 'UNKNOWN_FAILURE',
+};
diff --git a/ui/components/app/ledger-instruction-field/ledger-instruction-field.js b/ui/components/app/ledger-instruction-field/ledger-instruction-field.js
index 960b6ca07..287db2c8e 100644
--- a/ui/components/app/ledger-instruction-field/ledger-instruction-field.js
+++ b/ui/components/app/ledger-instruction-field/ledger-instruction-field.js
@@ -5,6 +5,7 @@ import {
   LEDGER_TRANSPORT_TYPES,
   LEDGER_USB_VENDOR_ID,
   WEBHID_CONNECTED_STATUSES,
+  TRANSPORT_STATES,
 } from '../../../../shared/constants/hardware-wallets';
 import {
   PLATFORM_FIREFOX,
@@ -14,6 +15,8 @@ import {
 import {
   setLedgerWebHidConnectedStatus,
   getLedgerWebHidConnectedStatus,
+  setLedgerTransportStatus,
+  getLedgerTransportStatus,
 } from '../../../ducks/app/app';
 
 import Typography from '../../ui/typography/typography';
@@ -30,6 +33,7 @@ import {
   getEnvironmentType,
 } from '../../../../app/scripts/lib/util';
 import { getLedgerTransportType } from '../../../ducks/metamask/metamask';
+import { attemptLedgerTransportCreation } from '../../../store/actions';
 
 const renderInstructionStep = (text, show = true, color = COLORS.PRIMARY3) => {
   return (
@@ -52,6 +56,7 @@ export default function LedgerInstructionField({ showDataInstruction }) {
 
   const webHidConnectedStatus = useSelector(getLedgerWebHidConnectedStatus);
   const ledgerTransportType = useSelector(getLedgerTransportType);
+  const transportStatus = useSelector(getLedgerTransportStatus);
   const environmentType = getEnvironmentType();
   const environmentTypeIsFullScreen =
     environmentType === ENVIRONMENT_TYPE_FULLSCREEN;
@@ -75,8 +80,45 @@ export default function LedgerInstructionField({ showDataInstruction }) {
         );
       }
     };
+    const determineTransportStatus = async () => {
+      if (
+        ledgerTransportType === LEDGER_TRANSPORT_TYPES.WEBHID &&
+        webHidConnectedStatus === WEBHID_CONNECTED_STATUSES.CONNECTED &&
+        transportStatus === TRANSPORT_STATES.NONE
+      ) {
+        try {
+          const transportedCreated = await attemptLedgerTransportCreation();
+          dispatch(
+            setLedgerTransportStatus(
+              transportedCreated
+                ? TRANSPORT_STATES.VERIFIED
+                : TRANSPORT_STATES.UNKNOWN_FAILURE,
+            ),
+          );
+        } catch (e) {
+          if (e.message.match('Failed to open the device')) {
+            dispatch(
+              setLedgerTransportStatus(TRANSPORT_STATES.DEVICE_OPEN_FAILURE),
+            );
+          } else if (e.message.match('the device is already open')) {
+            dispatch(setLedgerTransportStatus(TRANSPORT_STATES.VERIFIED));
+          } else {
+            dispatch(
+              setLedgerTransportStatus(TRANSPORT_STATES.UNKNOWN_FAILURE),
+            );
+          }
+        }
+      }
+    };
+    determineTransportStatus();
     initialConnectedDeviceCheck();
-  }, [dispatch, ledgerTransportType, webHidConnectedStatus]);
+  }, [dispatch, ledgerTransportType, webHidConnectedStatus, transportStatus]);
+
+  useEffect(() => {
+    return () => {
+      dispatch(setLedgerTransportStatus(TRANSPORT_STATES.NONE));
+    };
+  }, [dispatch]);
 
   const usingLedgerLive = ledgerTransportType === LEDGER_TRANSPORT_TYPES.LIVE;
   const usingWebHID = ledgerTransportType === LEDGER_TRANSPORT_TYPES.WEBHID;
@@ -104,6 +146,23 @@ export default function LedgerInstructionField({ showDataInstruction }) {
               `- ${t('ledgerConnectionInstructionStepFour')}`,
               showDataInstruction,
             )}
+            {renderInstructionStep(
+              <span>
+                <Button
+                  type="link"
+                  onClick={async () => {
+                    if (environmentTypeIsFullScreen) {
+                      window.location.reload();
+                    } else {
+                      global.platform.openExtensionInBrowser(null, null, true);
+                    }
+                  }}
+                >
+                  {t('ledgerConnectionInstructionCloseOtherApps')}
+                </Button>
+              </span>,
+              transportStatus === TRANSPORT_STATES.DEVICE_OPEN_FAILURE,
+            )}
             {renderInstructionStep(
               <span>
                 <Button
diff --git a/ui/ducks/app/app.js b/ui/ducks/app/app.js
index 517b72471..f9ea58daa 100644
--- a/ui/ducks/app/app.js
+++ b/ui/ducks/app/app.js
@@ -1,4 +1,7 @@
-import { WEBHID_CONNECTED_STATUSES } from '../../../shared/constants/hardware-wallets';
+import {
+  WEBHID_CONNECTED_STATUSES,
+  TRANSPORT_STATES,
+} from '../../../shared/constants/hardware-wallets';
 import * as actionConstants from '../../store/actionConstants';
 
 // actionConstants
@@ -50,6 +53,7 @@ export default function reduceApp(state = {}, action) {
     },
     gasLoadingAnimationIsShowing: false,
     ledgerWebHidConnectedStatus: WEBHID_CONNECTED_STATUSES.UNKNOWN,
+    ledgerTransportStatus: TRANSPORT_STATES.NONE,
     ...state,
   };
 
@@ -348,6 +352,12 @@ export default function reduceApp(state = {}, action) {
         ledgerWebHidConnectedStatus: action.value,
       };
 
+    case actionConstants.SET_LEDGER_TRANSPORT_STATUS:
+      return {
+        ...appState,
+        ledgerTransportStatus: action.value,
+      };
+
     default:
       return appState;
   }
@@ -375,6 +385,10 @@ export function setLedgerWebHidConnectedStatus(value) {
   return { type: actionConstants.SET_WEBHID_CONNECTED_STATUS, value };
 }
 
+export function setLedgerTransportStatus(value) {
+  return { type: actionConstants.SET_LEDGER_TRANSPORT_STATUS, value };
+}
+
 // Selectors
 export function getQrCodeData(state) {
   return state.appState.qrCodeData;
@@ -387,3 +401,7 @@ export function getGasLoadingAnimationIsShowing(state) {
 export function getLedgerWebHidConnectedStatus(state) {
   return state.appState.ledgerWebHidConnectedStatus;
 }
+
+export function getLedgerTransportStatus(state) {
+  return state.appState.ledgerTransportStatus;
+}
diff --git a/ui/selectors/selectors.js b/ui/selectors/selectors.js
index a0de92a40..af65b2d8a 100644
--- a/ui/selectors/selectors.js
+++ b/ui/selectors/selectors.js
@@ -10,6 +10,7 @@ import {
   KEYRING_TYPES,
   WEBHID_CONNECTED_STATUSES,
   LEDGER_TRANSPORT_TYPES,
+  TRANSPORT_STATES,
 } from '../../shared/constants/hardware-wallets';
 
 import {
@@ -42,7 +43,10 @@ import {
   isAddressLedger,
   findKeyringForAddress,
 } from '../ducks/metamask/metamask';
-import { getLedgerWebHidConnectedStatus } from '../ducks/app/app';
+import {
+  getLedgerWebHidConnectedStatus,
+  getLedgerTransportStatus,
+} from '../ducks/app/app';
 
 /**
  * One of the only remaining valid uses of selecting the network subkey of the
@@ -657,8 +661,13 @@ export function doesAddressRequireLedgerHidConnection(state, address) {
   const webHidIsNotConnected =
     getLedgerWebHidConnectedStatus(state) !==
     WEBHID_CONNECTED_STATUSES.CONNECTED;
+  const ledgerTransportStatus = getLedgerTransportStatus(state);
+  const transportIsNotSuccessfullyCreated =
+    ledgerTransportStatus !== TRANSPORT_STATES.VERIFIED;
 
   return (
-    addressIsLedger && transportTypePreferenceIsWebHID && webHidIsNotConnected
+    addressIsLedger &&
+    transportTypePreferenceIsWebHID &&
+    (webHidIsNotConnected || transportIsNotSuccessfullyCreated)
   );
 }
diff --git a/ui/store/actionConstants.js b/ui/store/actionConstants.js
index 5f70a4304..b1724fad3 100644
--- a/ui/store/actionConstants.js
+++ b/ui/store/actionConstants.js
@@ -80,6 +80,7 @@ export const SET_MOUSE_USER_STATE = 'SET_MOUSE_USER_STATE';
 // Ledger
 
 export const SET_WEBHID_CONNECTED_STATUS = 'SET_WEBHID_CONNECTED_STATUS';
+export const SET_LEDGER_TRANSPORT_STATUS = 'SET_LEDGER_TRANSPORT_STATUS';
 
 // Network
 export const SET_PENDING_TOKENS = 'SET_PENDING_TOKENS';
diff --git a/ui/store/actions.js b/ui/store/actions.js
index e94779498..aeca70147 100644
--- a/ui/store/actions.js
+++ b/ui/store/actions.js
@@ -2770,6 +2770,10 @@ export function setLedgerLivePreference(value) {
   };
 }
 
+export async function attemptLedgerTransportCreation() {
+  return await promisifiedBackground.attemptLedgerTransportCreation();
+}
+
 export function captureSingleException(error) {
   return async (dispatch, getState) => {
     const { singleExceptions } = getState().appState;
diff --git a/yarn.lock b/yarn.lock
index 9e1b5695b..b0a238851 100644
--- a/yarn.lock
+++ b/yarn.lock
@@ -2821,10 +2821,10 @@
   resolved "https://registry.yarnpkg.com/@metamask/eslint-config/-/eslint-config-6.0.0.tgz#ec53e8ab278073e882411ed89705bc7d06b78c81"
   integrity sha512-LyakGYGwM8UQOGhwWa+5erAI1hXuiTgf/y7USzOomX6H9KiuY09IAUYnPh7ToPG2sedD2F48UF1bUm8yvCoZOw==
 
-"@metamask/eth-ledger-bridge-keyring@^0.9.0":
-  version "0.9.0"
-  resolved "https://registry.yarnpkg.com/@metamask/eth-ledger-bridge-keyring/-/eth-ledger-bridge-keyring-0.9.0.tgz#42e98e7dfeaaa08e7c9ceff261facddd7320df80"
-  integrity sha512-EuNKvodbdJxQPzr+zAE5TE1iKUzuIRWKeVaYoYwpi18RjjtSQMKmZcb3VXY8hmQu+Fj4Ld/ujj22qSYjYAjtPg==
+"@metamask/eth-ledger-bridge-keyring@^0.10.0":
+  version "0.10.0"
+  resolved "https://registry.yarnpkg.com/@metamask/eth-ledger-bridge-keyring/-/eth-ledger-bridge-keyring-0.10.0.tgz#9d5103be22221f4ef71393a2e11f24b788e343a5"
+  integrity sha512-ewcnEFmIL2lkUta811yQeJVWhTjll9U62GdbuauvxdQ0c6VBGZnf02GU3gcxyMOcEvZBnlU+d5LWpURQA8iNZQ==
   dependencies:
     "@ethereumjs/tx" "^3.2.0"
     eth-sig-util "^2.0.0"