diff --git a/app/src/flux/stores/identity-store.ts b/app/src/flux/stores/identity-store.ts
index aecebb65f..d79f0069d 100644
--- a/app/src/flux/stores/identity-store.ts
+++ b/app/src/flux/stores/identity-store.ts
@@ -10,7 +10,7 @@ import { makeRequest, rootURLForServer } from '../mailspring-api-request';
 import { Disposable } from 'event-kit';
 
 // Note this key name is used when migrating to Mailspring Pro accounts from old N1.
-const KEYCHAIN_NAME = 'Mailspring Account';
+const PASSWORD_NAME = 'Mailspring Account';
 
 export interface IIdentity {
   id: string;
@@ -41,6 +41,7 @@ export const EMPTY_FEATURE_USAGE = {
 
 class _IdentityStore extends MailspringStore {
   _identity: IIdentity = null;
+  _displayedPasswordError = false;
   _disp: Disposable;
 
   constructor() {
@@ -98,7 +99,7 @@ class _IdentityStore extends MailspringStore {
   async saveIdentity(identity: IIdentity | null) {
     if (!identity) {
       this._identity = null;
-      await KeyManager.deletePassword(KEYCHAIN_NAME);
+      await KeyManager.deletePassword(PASSWORD_NAME);
       AppEnv.config.set('identity', null);
       return;
     }
@@ -114,7 +115,7 @@ class _IdentityStore extends MailspringStore {
       // Note: We /must/ await this because calling config.set below
       // will try to retrieve the password via getPassword.
       // If this fails, the app may quit here.
-      await KeyManager.replacePassword(KEYCHAIN_NAME, nextToken);
+      await KeyManager.replacePassword(PASSWORD_NAME, nextToken);
     }
 
     this._identity = identity;
@@ -132,8 +133,20 @@ class _IdentityStore extends MailspringStore {
   _onIdentityChanged = async () => {
     const value = AppEnv.config.get('identity');
     this._identity = value
-      ? { ...value, token: await KeyManager.getPassword(KEYCHAIN_NAME) }
+      ? { ...value, token: await KeyManager.getPassword(PASSWORD_NAME) }
       : null;
+
+    if (this._identity && !this._identity.token) {
+      const message = `Your Mailspring ID password could not be loaded from your keychain. Please visit Preferences > Subscription and click "Setup Mailspring ID" to sign in to your Mailspring account again.\n\nYour Mailspring ID email address is ${this._identity.emailAddress}.`;
+      console.warn(message);
+
+      if (!this._displayedPasswordError) {
+        this._displayedPasswordError = true;
+        AppEnv.showErrorDialog({ title: 'Please Sign In', message });
+      }
+      this._identity = null;
+    }
+
     this.trigger();
   };
 
diff --git a/app/src/key-manager.ts b/app/src/key-manager.ts
index f19cba403..4e0926b17 100644
--- a/app/src/key-manager.ts
+++ b/app/src/key-manager.ts
@@ -5,7 +5,7 @@ interface KeySet {
   [key: string]: string;
 }
 
-const { safeStorage } = require("@electron/remote");
+const { safeStorage } = require('@electron/remote');
 
 const configCredentialsKey = 'credentials';
 
@@ -18,7 +18,6 @@ const configCredentialsKey = 'credentials';
  * and every key we want to access.
  */
 class KeyManager {
-
   async deleteAccountSecrets(account: Account) {
     try {
       const keys = await this._getKeyHash();
@@ -90,8 +89,17 @@ class KeyManager {
     let raw = '{}';
     const encryptedCredentials = AppEnv.config.get(configCredentialsKey);
     // Check for different null values to prevent issues if a migration from keytar has failed
-    if (encryptedCredentials !== undefined && encryptedCredentials !== null && encryptedCredentials !== "null") {
-      raw = await safeStorage.decryptString(Buffer.from(encryptedCredentials, "utf-8"));
+    if (
+      encryptedCredentials !== undefined &&
+      encryptedCredentials !== null &&
+      encryptedCredentials !== 'null'
+    ) {
+      try {
+        raw = await safeStorage.decryptString(Buffer.from(encryptedCredentials, 'utf-8'));
+      } catch (err) {
+        console.error('Mailspring encountered an error reading passwords from the keychain.');
+        console.error(err);
+      }
     }
     try {
       return JSON.parse(raw) as KeySet;
@@ -101,7 +109,7 @@ class KeyManager {
   }
 
   async _writeKeyHash(keys: KeySet) {
-    const enrcyptedCredentials = await safeStorage.encryptString(JSON.stringify(keys))
+    const enrcyptedCredentials = await safeStorage.encryptString(JSON.stringify(keys));
     AppEnv.config.set(configCredentialsKey, enrcyptedCredentials);
   }
 
@@ -117,7 +125,7 @@ class KeyManager {
 
     if (clickedButton == 0) {
       const shell = require('electron').shell;
-      shell.openExternal("https://community.getmailspring.com/t/password-management-error/199")
+      shell.openExternal('https://community.getmailspring.com/t/password-management-error/199');
     }
 
     // tell the app to exit and rethrow the error to ensure code relying