diff --git a/extension/chrome/elements/add_pubkey.htm b/extension/chrome/elements/add_pubkey.htm
index 78c0b986eff..2cc80a3f4bd 100644
--- a/extension/chrome/elements/add_pubkey.htm
+++ b/extension/chrome/elements/add_pubkey.htm
@@ -1,6 +1,6 @@
 <!-- © 2016-2018 FlowCrypt Limited. Limitations apply. Contact human@flowcrypt.com -->
 
-<!DOCTYPE html>
+<!doctype html>
 <html>
   <head>
     <meta content="text/html;charset=utf-8" http-equiv="Content-Type" />
@@ -12,7 +12,7 @@
     <link rel="stylesheet" href="/css/open-sans.css" />
     <link rel="stylesheet" href="/css/mobile-menu-styling.css" />
     <link rel="stylesheet" href="/css/fine-uploader-new.css" />
-    <script type="text/template" src="/chrome/elements/hared/attach.template.htm" id="qq-template"></script>
+    <script type="text/template" src="/chrome/elements/shared/attach.template.htm" id="qq-template"></script>
   </head>
 
   <body id="settings">
diff --git a/extension/chrome/settings/modules/add_key.htm b/extension/chrome/settings/modules/add_key.htm
index b8ef788c1f1..9d07dfc8295 100644
--- a/extension/chrome/settings/modules/add_key.htm
+++ b/extension/chrome/settings/modules/add_key.htm
@@ -12,7 +12,7 @@
     <link rel="icon" href="/img/logo/flowcrypt-logo-19-19.png" />
     <link rel="stylesheet" href="/css/fine-uploader-new.css" />
     <link rel="stylesheet" href="/css/mobile-menu-styling.css" />
-    <script type="text/template" src="/chrome/elements/hared/attach.template.htm" id="qq-template"></script>
+    <script type="text/template" src="/chrome/elements/shared/attach.template.htm" id="qq-template"></script>
   </head>
 
   <body id="settings">
diff --git a/extension/chrome/settings/modules/add_key.ts b/extension/chrome/settings/modules/add_key.ts
index c64ba25cef8..7198c26ed28 100644
--- a/extension/chrome/settings/modules/add_key.ts
+++ b/extension/chrome/settings/modules/add_key.ts
@@ -98,10 +98,13 @@ View.run(
 
     private saveKeyAndContinue = async (key: Key) => {
       await saveKeysAndPassPhrase(this.acctEmail, [key]); // resulting new_key checked above
+      /* eslint-disable @typescript-eslint/naming-convention */
       await setPassphraseForPrvs(this.clientConfiguration, this.acctEmail, [key], {
         passphrase: String($('.input_passphrase').val()),
-        passphrase_save: !!$('.input_passphrase_save').prop('checked'), // eslint-disable-line , @typescript-eslint/naming-convention
+        passphrase_save: !!$('.input_passphrase_save').prop('checked'),
+        passphrase_ensure_single_copy: false, // we require KeyImportUi to rejectKnown keys
       });
+      /* eslint-enable @typescript-eslint/naming-convention */
       BrowserMsg.send.reload(this.parentTabId, { advanced: true });
     };
 
diff --git a/extension/chrome/settings/modules/contacts.htm b/extension/chrome/settings/modules/contacts.htm
index 5f2f0b3126f..8c799625e17 100644
--- a/extension/chrome/settings/modules/contacts.htm
+++ b/extension/chrome/settings/modules/contacts.htm
@@ -12,7 +12,7 @@
     <link rel="stylesheet" href="/css/mobile-menu-styling.css" />
     <link rel="icon" href="/img/logo/flowcrypt-logo-19-19.png" />
     <link rel="stylesheet" href="/css/fine-uploader-new.css" />
-    <script type="text/template" src="/chrome/elements/hared/attach.template.htm" id="qq-template"></script>
+    <script type="text/template" src="/chrome/elements/shared/attach.template.htm" id="qq-template"></script>
     <style>
       #fineuploader_button {
         overflow: initial !important;
diff --git a/extension/chrome/settings/modules/decrypt.htm b/extension/chrome/settings/modules/decrypt.htm
index 49fa8b344d4..69cfa52a852 100644
--- a/extension/chrome/settings/modules/decrypt.htm
+++ b/extension/chrome/settings/modules/decrypt.htm
@@ -9,7 +9,7 @@
     <link rel="stylesheet" href="/css/sweetalert2.css" />
     <link rel="stylesheet" href="/css/open-sans.css" />
     <link rel="stylesheet" href="/css/fine-uploader-new.css" />
-    <script type="text/template" src="/chrome/elements/hared/attach.template.htm" id="qq-template"></script>
+    <script type="text/template" src="/chrome/elements/shared/attach.template.htm" id="qq-template"></script>
     <style>
       iframe {
         width: 100%;
diff --git a/extension/chrome/settings/modules/my_key_update.htm b/extension/chrome/settings/modules/my_key_update.htm
index 68a24332838..d031fa5a486 100644
--- a/extension/chrome/settings/modules/my_key_update.htm
+++ b/extension/chrome/settings/modules/my_key_update.htm
@@ -11,6 +11,8 @@
     <link rel="stylesheet" href="/css/animate.css" />
     <link rel="stylesheet" href="/css/mobile-menu-styling.css" />
     <link rel="icon" href="/img/logo/flowcrypt-logo-19-19.png" />
+    <link rel="stylesheet" href="/css/fine-uploader-new.css" />
+    <script type="text/template" src="/chrome/elements/shared/attach.template.htm" id="qq-template"></script>
   </head>
 
   <body id="settings">
@@ -21,16 +23,35 @@
       </div>
       <div class="line">FlowCrypt will also recreate a new public key from your updated private key.</div>
       <div class="line">
-        <textarea class="input_private_key armored" data-test="input-prv-key" placeholder="Updated ASCII Armored Private Key" maxlength="80000"></textarea>
+        <ul style="list-style: none; margin-left: 0; padding-left: 0" class="source_selector display_none">
+          <li>
+            <input type="radio" name="source" id="source_file" data-test="source-file" value="file" />
+            <label for="source_file"> Load from a file</label>
+          </li>
+          <li>
+            <input type="radio" name="source" id="source_paste" data-test="source-paste" value="paste" />
+            <label for="source_paste"> Paste armored key directly </label>
+          </li>
+        </ul>
       </div>
-      <div class="line">
-        <input class="input_passphrase" type="password" data-test="input-passphrase" placeholder="Private Key Passphrase" maxlength="256" />
+      <div class="source_file_container display_none">
+        <a href="#" id="fineuploader_button" class="display_none">file</a>
+        <div class="line display_none" id="fineuploader"></div>
+      </div>
+      <div class="source_paste_container display_none">
+        <div class="line">
+          <textarea class="input_private_key armored" data-test="input-prv-key" placeholder="Updated ASCII Armored Private Key" maxlength="80000"></textarea>
+        </div>
+        <div class="line">
+          <input class="input_passphrase" type="password" data-test="input-passphrase" placeholder="Private Key Passphrase" maxlength="256" />
+        </div>
+        <div class="line"><span class="button green long action_update_private_key" data-test="action-update-key">update private key</span></div>
       </div>
-      <div class="line"><span class="button green long action_update_private_key" data-test="action-update-key">update private key</span></div>
       <div class="line"><a href="#" class="action_show_public_key">Back to Public Key</a></div>
     </div>
 
     <script src="/lib/purify.js"></script>
+    <script src="/lib/fine-uploader.js"></script>
     <script src="/lib/jquery.min.js"></script>
     <script src="/lib/sweetalert2.js"></script>
     <script src="/lib/openpgp.js"></script>
diff --git a/extension/chrome/settings/modules/my_key_update.ts b/extension/chrome/settings/modules/my_key_update.ts
index 9eb6f66497a..4315db69c75 100644
--- a/extension/chrome/settings/modules/my_key_update.ts
+++ b/extension/chrome/settings/modules/my_key_update.ts
@@ -19,11 +19,14 @@ import { PassphraseStore } from '../../../js/common/platform/store/passphrase-st
 import { AcctStore } from '../../../js/common/platform/store/acct-store.js';
 import { InMemoryStore } from '../../../js/common/platform/store/in-memory-store.js';
 import { InMemoryStoreKeys } from '../../../js/common/core/const.js';
+import { KeyImportUi } from '../../../js/common/ui/key-import-ui.js';
+import { saveKeysAndPassPhrase } from '../../../js/common/helpers.js';
 
 View.run(
   class MyKeyUpdateView extends View {
     protected fesUrl?: string;
     private readonly acctEmail: string;
+    private readonly keyImportUi = new KeyImportUi({});
     private readonly fingerprint: string;
     private readonly showKeyUrl: string;
     private readonly inputPrivateKey = $('.input_private_key');
@@ -57,6 +60,7 @@ View.run(
         );
       } else {
         $('#content').show();
+        this.keyImportUi.initPrvImportSrcForm(this.acctEmail, undefined);
         this.pubLookup = new PubLookup(this.clientConfiguration);
         [this.ki] = await KeyStore.get(this.acctEmail, [this.fingerprint]);
         Assert.abortAndRenderErrorIfKeyinfoEmpty(this.ki ? [this.ki] : []);
@@ -64,6 +68,7 @@ View.run(
         $('.email').text(this.acctEmail);
         $('.fingerprint').text(Str.spaced(this.ki.fingerprints[0]));
         this.inputPrivateKey.attr('placeholder', this.inputPrivateKey.attr('placeholder') + ' (' + this.ki.fingerprints[0] + ')');
+        $('.source_selector').css('display', 'block');
       }
     };
 
@@ -76,13 +81,10 @@ View.run(
     };
 
     private storeUpdatedKeyAndPassphrase = async (updatedPrv: Key, updatedPrvPassphrase: string) => {
-      /* eslint-disable @typescript-eslint/no-non-null-assertion */
-      const shouldSavePassphraseInStorage =
-        !this.clientConfiguration.forbidStoringPassPhrase() && !!(await PassphraseStore.get(this.acctEmail, this.ki!, true));
-      await KeyStore.add(this.acctEmail, updatedPrv);
-      await PassphraseStore.set('local', this.acctEmail, this.ki!, shouldSavePassphraseInStorage ? updatedPrvPassphrase : undefined);
-      await PassphraseStore.set('session', this.acctEmail, this.ki!, shouldSavePassphraseInStorage ? undefined : updatedPrvPassphrase);
-      /* eslint-enable @typescript-eslint/no-non-null-assertion */
+      /* eslint-disable @typescript-eslint/no-non-null-assertion, @typescript-eslint/naming-convention */
+      const passphrase_save = !this.clientConfiguration.forbidStoringPassPhrase() && !!(await PassphraseStore.get(this.acctEmail, this.ki!, true));
+      await saveKeysAndPassPhrase(this.acctEmail, [updatedPrv], { passphrase: updatedPrvPassphrase, passphrase_save, passphrase_ensure_single_copy: true });
+      /* eslint-enable @typescript-eslint/no-non-null-assertion, @typescript-eslint/naming-convention */
       if (
         this.clientConfiguration.canSubmitPubToAttester() &&
         (await Ui.modal.confirm('Public and private key updated locally.\n\nUpdate public records with new Public Key?'))
@@ -101,11 +103,14 @@ View.run(
     };
 
     private updatePrivateKeyHandler = async () => {
-      const updatedKey = await KeyUtil.parse(String(this.inputPrivateKey.val()));
       const updatedKeyEncrypted = await KeyUtil.parse(String(this.inputPrivateKey.val()));
+      const updatedKey = await KeyUtil.parse(KeyUtil.armor(updatedKeyEncrypted)); // create a "cloned" copy to decrypt later
       const updatedKeyPassphrase = String($('.input_passphrase').val());
+      KeyImportUi.allowReselect();
       if (typeof updatedKey === 'undefined') {
         await Ui.modal.warning(Lang.setup.keyFormattedWell(this.prvHeaders.begin, String(this.prvHeaders.end)), Ui.testCompatibilityLink);
+      } else if (updatedKeyEncrypted.identities.length === 0) {
+        await Ui.modal.error(Lang.setup.prvHasUseridIssue);
       } else if (updatedKey.isPublic) {
         await Ui.modal.warning(
           'This was a public key. Please insert a private key instead. It\'s a block of text starting with "' + this.prvHeaders.begin + '"'
diff --git a/extension/chrome/settings/setup.htm b/extension/chrome/settings/setup.htm
index 13e618e1686..0b6babb8753 100644
--- a/extension/chrome/settings/setup.htm
+++ b/extension/chrome/settings/setup.htm
@@ -14,7 +14,7 @@
     <link rel="stylesheet" href="/lib/bootstrap/bootstrap.min.css" />
     <link rel="stylesheet" href="/css/mobile-menu-styling.css" />
     <link rel="icon" href="/img/logo/flowcrypt-logo-19-19.png" />
-    <script type="text/template" src="/chrome/elements/hared/attach.template.htm" id="qq-template"></script>
+    <script type="text/template" src="/chrome/elements/shared/attach.template.htm" id="qq-template"></script>
   </head>
 
   <body id="settings">
diff --git a/extension/chrome/settings/setup.ts b/extension/chrome/settings/setup.ts
index 021dba1f7ae..74ced4d089d 100644
--- a/extension/chrome/settings/setup.ts
+++ b/extension/chrome/settings/setup.ts
@@ -38,7 +38,8 @@ import { InMemoryStore } from '../../js/common/platform/store/in-memory-store.js
 /* eslint-disable @typescript-eslint/naming-convention */
 export interface PassphraseOptions {
   passphrase: string;
-  passphrase_save: boolean;
+  passphrase_save: boolean; // if true and not forbidden by OrgRules, save to the local storage, otherwise to session
+  passphrase_ensure_single_copy: boolean; // make sure the passphrase isn't both in local storage and session
 }
 
 export interface SetupOptions extends PassphraseOptions {
diff --git a/extension/chrome/settings/setup/setup-create-key.ts b/extension/chrome/settings/setup/setup-create-key.ts
index 884ae45a1a3..bd634347f1b 100644
--- a/extension/chrome/settings/setup/setup-create-key.ts
+++ b/extension/chrome/settings/setup/setup-create-key.ts
@@ -27,6 +27,7 @@ export class SetupCreateKeyModule {
       const opts: SetupOptions = {
         passphrase: String($('#step_2a_manual_create .input_password').val()),
         passphrase_save: Boolean($('#step_2a_manual_create .input_passphrase_save').prop('checked')),
+        passphrase_ensure_single_copy: false, // there can't be any saved passphrases for the new key
         submit_main: this.view.shouldSubmitPubkey('#step_2a_manual_create .input_submit_key'),
         submit_all: this.view.shouldSubmitPubkey('#step_2a_manual_create .input_submit_all'),
         recovered: false,
diff --git a/extension/chrome/settings/setup/setup-import-key.ts b/extension/chrome/settings/setup/setup-import-key.ts
index cca3d9d5df0..257c0f3f8b2 100644
--- a/extension/chrome/settings/setup/setup-import-key.ts
+++ b/extension/chrome/settings/setup/setup-import-key.ts
@@ -27,6 +27,7 @@ export class SetupImportKeyModule {
       submit_main: this.view.shouldSubmitPubkey('#step_2b_manual_enter .input_submit_key'),
       submit_all: this.view.shouldSubmitPubkey('#step_2b_manual_enter .input_submit_all'),
       passphrase_save: Boolean($('#step_2b_manual_enter .input_passphrase_save').prop('checked')),
+      passphrase_ensure_single_copy: true,
       recovered: false,
     };
     /* eslint-enable @typescript-eslint/naming-convention */
diff --git a/extension/chrome/settings/setup/setup-key-manager-autogen.ts b/extension/chrome/settings/setup/setup-key-manager-autogen.ts
index 35aa342518e..4330eba3386 100644
--- a/extension/chrome/settings/setup/setup-key-manager-autogen.ts
+++ b/extension/chrome/settings/setup/setup-key-manager-autogen.ts
@@ -47,6 +47,7 @@ export class SetupWithEmailKeyManagerModule {
     const setupOptions: SetupOptions = {
       passphrase_save:
         this.view.clientConfiguration.mustAutogenPassPhraseQuietly() || Boolean($('#step_2_ekm_choose_pass_phrase .input_passphrase_save').prop('checked')),
+      passphrase_ensure_single_copy: false, // there can't be any saved passphrases for the new key
       submit_main: this.view.clientConfiguration.canSubmitPubToAttester(),
       submit_all: false,
       passphrase,
diff --git a/extension/chrome/settings/setup/setup-recover-key.ts b/extension/chrome/settings/setup/setup-recover-key.ts
index 6468af2b915..5eb03aff83a 100644
--- a/extension/chrome/settings/setup/setup-recover-key.ts
+++ b/extension/chrome/settings/setup/setup-recover-key.ts
@@ -63,6 +63,7 @@ export class SetupRecoverKeyModule {
         submit_all: false,
         passphrase,
         passphrase_save: true, // todo - reevaluate saving passphrase when recovering
+        passphrase_ensure_single_copy: true,
         recovered: true,
       };
       await saveKeysAndPassPhrase(this.view.acctEmail, newlyMatchingKeys, options);
diff --git a/extension/js/common/helpers.ts b/extension/js/common/helpers.ts
index a5378e1d326..0f20e9f6683 100644
--- a/extension/js/common/helpers.ts
+++ b/extension/js/common/helpers.ts
@@ -20,7 +20,12 @@ export const isCustomerUrlFesUsed = async (acctEmail: string) => {
 export const setPassphraseForPrvs = async (clientConfiguration: ClientConfiguration, acctEmail: string, prvs: Key[], ppOptions: PassphraseOptions) => {
   const storageType = ppOptions.passphrase_save && !clientConfiguration.forbidStoringPassPhrase() ? 'local' : 'session';
   for (const prv of prvs) {
-    await PassphraseStore.set(storageType, acctEmail, { longid: KeyUtil.getPrimaryLongid(prv) }, ppOptions.passphrase);
+    const keyInfo = { longid: KeyUtil.getPrimaryLongid(prv) };
+    await PassphraseStore.set(storageType, acctEmail, keyInfo, ppOptions.passphrase);
+    if (ppOptions.passphrase_ensure_single_copy) {
+      // delete from the other storage
+      await PassphraseStore.set(storageType === 'local' ? 'session' : 'local', acctEmail, { longid: KeyUtil.getPrimaryLongid(prv) }, undefined);
+    }
   }
 };
 
@@ -41,8 +46,6 @@ const addOrReplaceKeysAndPassPhrase = async (acctEmail: string, prvs: Key[], ppO
     }
   }
   if (ppOptions !== undefined) {
-    // todo: it would be good to check that the passphrase isn't present in the other storage type
-    //    though this situation is not possible with current use cases
     await setPassphraseForPrvs(await ClientConfiguration.newInstance(acctEmail), acctEmail, prvs, ppOptions);
   }
   const { sendAs, full_name: name } = await AcctStore.get(acctEmail, ['sendAs', 'full_name']);
@@ -125,7 +128,7 @@ export const processAndStoreKeysFromEkmLocally = async ({
   let ppOptions: PassphraseOptions | undefined; // the options to pass to saveKeysAndPassPhrase
   if (!originalOptions?.passphrase && (await ClientConfiguration.newInstance(acctEmail)).mustAutogenPassPhraseQuietly()) {
     // eslint-disable-next-line @typescript-eslint/naming-convention
-    ppOptions = { passphrase: PgpPwd.random(), passphrase_save: true };
+    ppOptions = { passphrase: PgpPwd.random(), passphrase_save: true, passphrase_ensure_single_copy: true };
   } else {
     ppOptions = originalOptions;
   }
@@ -163,7 +166,7 @@ export const processAndStoreKeysFromEkmLocally = async ({
   if (encryptedKeys?.keys.length) {
     // new keys are about to be added, they must be accompanied with the passphrase setting
     // eslint-disable-next-line @typescript-eslint/naming-convention
-    const effectivePpOptions = { passphrase: encryptedKeys.passphrase, passphrase_save: passphraseInLocalStorage };
+    const effectivePpOptions = { passphrase: encryptedKeys.passphrase, passphrase_save: passphraseInLocalStorage, passphrase_ensure_single_copy: true };
     // ppOptions have special meaning in saveKeysAndPassPhrase(), they trigger `name` updates, todo: refactor in #4545
     await saveKeysAndPassPhrase(acctEmail, encryptedKeys.keys, ppOptions ? effectivePpOptions : undefined);
     if (!ppOptions) {
diff --git a/extension/js/common/lang.ts b/extension/js/common/lang.ts
index 5194ec2a9a6..41f2798933c 100644
--- a/extension/js/common/lang.ts
+++ b/extension/js/common/lang.ts
@@ -46,6 +46,7 @@ export const Lang = {
     keyBackupsNotAllowed: 'Key backups are not allowed on this domain.',
     prvHasFixableCompatIssue:
       'This key has minor usability issues that can be fixed. This commonly happens when importing keys from Symantec&trade; PGP Desktop or other legacy software. It may be missing User IDs, or it may be missing a self-signature. It is also possible that the key is simply expired.',
+    prvHasUseridIssue: 'The set of User IDs in this key is not supported.',
     ppMatchAllSet: "Your pass phrase matches. Good job! You're all set.",
     noKeys: 'Keys for your account were not set up yet - please ask your systems administrator.',
   },
diff --git a/extension/js/common/ui/key-import-ui.ts b/extension/js/common/ui/key-import-ui.ts
index 67c0bc4a480..ab0dddf89d6 100644
--- a/extension/js/common/ui/key-import-ui.ts
+++ b/extension/js/common/ui/key-import-ui.ts
@@ -76,6 +76,11 @@ export class KeyImportUi {
     submitKeyForAddrs.splice(submitKeyForAddrs.indexOf(email), 1);
   };
 
+  // by unselecting, we allow to click on "Load from a file" and trigger the fineuploader again
+  public static allowReselect = () => {
+    $('input[type=radio][name=source]').prop('checked', false);
+  };
+
   public onBadPassphrase: VoidCallback = () => undefined;
 
   public initPrvImportSrcForm = (acctEmail: string, parentTabId: string | undefined, submitKeyForAddrs?: string[] | undefined) => {
@@ -181,7 +186,7 @@ export class KeyImportUi {
         } else {
           $('.input_private_key').val('').change().prop('disabled', false);
           await Ui.modal.error('Not able to read this key. Make sure it is a valid PGP private key.', false, Ui.testCompatibilityLink);
-          $('input[type=radio][name=source]').removeAttr('checked');
+          KeyImportUi.allowReselect();
         }
       },
     });
@@ -310,7 +315,7 @@ export class KeyImportUi {
       throw new UserAlert('This was a public key. Please insert a private key instead. It\'s a block of text starting with "' + headers.begin + '"');
     }
     if (type === 'publicKey' && !k.isPublic) {
-      throw new UserAlert('This was a public key. Please insert a private key instead. It\'s a block of text starting with "' + headers.begin + '"');
+      throw new UserAlert('This was a private key. Please insert a public key instead. It\'s a block of text starting with "' + headers.begin + '"');
     }
   };
 
diff --git a/test/samples/openpgp/flowcrypttestkeymultiplegmailcom-0x98acfa1eadab5b92-original.asc b/test/samples/openpgp/flowcrypttestkeymultiplegmailcom-0x98acfa1eadab5b92-original.asc
new file mode 100644
index 00000000000..ee05ec07629
--- /dev/null
+++ b/test/samples/openpgp/flowcrypttestkeymultiplegmailcom-0x98acfa1eadab5b92-original.asc
@@ -0,0 +1,50 @@
+-----BEGIN PGP PRIVATE KEY BLOCK-----
+
+xcMGBF/3BtsBCADBoXomWXjSi7+Fu7b1eFOIQBNCVCtglgIc9Ko9EzyeNb8UcC8PKFALqgVSCbUD
+ziRTywdCB2c8yTM+bnAd960qOuL0ABVyE2gn+TVuXpnPG4LYUBbnIkBHCbyCklbWywzC9ir/r/kS
+uYf8ZJx+03cOZviJQRR+NHkv+NWKorJMIcG8DMsrmjz2FfC/YTLCEZSWagnAmnaPXpT9dLt+Jbxr
+vIEe0q02qVd+ueTL5mpxpVgGGuZ7AfsYcL8kwzYLNOE2Okg3szDLcSpKWiYTYF87dyjjjqa5qM1k
+kPZF+/ZJCTRmq0YxmQnZLxH6sOhmdhJz6VLQidyEoQh1xfALvc/5ABEBAAH+CQMIbcyquXWldvXx
+jB3M20MKc1NsiJiapv9WUYdwcbE0cK2QMzvCEWG0E3sFN+GABeiwdTl3jM0J+pJb2EhysO0nD5Bp
+yb9Ug3Vv5Sdyp4KYh45UV4mBd+ZWUXRE1ptxjlI3yasBXFI1TX6gmzq1GeReWXqC41RirXu9z0sf
+euFTX3ZTQslHI6uu+Z0OJZG5Jo1dtr6Z0FwmHop2AMUJGAGaLSrANI0kkHJvIPdkxeev6CORqisR
+U3APWezhH+ky4ptdxu3l7PrhXAEvUgpk4vVaA590X9m6ToAYFOqpObhXEFEcs4ZfJJmBQ8nO+9l0
+mQYKtIi81KWU8ogExGR/PyLdicnbMo6k1eSzOC/+5ch/PBTvVCW5r7FRJJsQ0evr3DT4QL958qRR
+LPPvAnnTJ4G5ajuzI83gYqunlszV4hY/wdLcLFJgs7NKhf1tZEkcZmbGxl/RBA1x8lAg8N1WH82V
+zc6RuqVkNipgFtJDFOcz/DxHm6swhMIyHSTCgku+XrDy+GeCfKZWqmPn64Lkl6DNJkUTGY3+RCXD
+8c5rHwyf7Xc9CF/x1qttRA8+QYpxEHSUEFZychSkddf66T335uk2I5lkiGQ9ho9HYFrQUMD4MQ9B
+DDncYvbALbFSjNDVkZGogBLgTWzwW/DHYeXR7q8MOT0U/QS2iCtLjJziYKH8l1sKFHiJTFg+OFXA
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+=Iqrh
+-----END PGP PRIVATE KEY BLOCK-----
\ No newline at end of file
diff --git a/test/samples/openpgp/flowcrypttestkeymultiplegmailcom-0x98acfa1eadab5b92-updated-userid-issue.key b/test/samples/openpgp/flowcrypttestkeymultiplegmailcom-0x98acfa1eadab5b92-updated-userid-issue.key
new file mode 100644
index 00000000000..a85861d8d79
Binary files /dev/null and b/test/samples/openpgp/flowcrypttestkeymultiplegmailcom-0x98acfa1eadab5b92-updated-userid-issue.key differ
diff --git a/test/samples/openpgp/flowcrypttestkeymultiplegmailcom-0x98acfa1eadab5b92-updated.key b/test/samples/openpgp/flowcrypttestkeymultiplegmailcom-0x98acfa1eadab5b92-updated.key
new file mode 100644
index 00000000000..03594321d24
Binary files /dev/null and b/test/samples/openpgp/flowcrypttestkeymultiplegmailcom-0x98acfa1eadab5b92-updated.key differ
diff --git a/test/source/tests/flaky.ts b/test/source/tests/flaky.ts
index 7355f3e58de..79c7b6ee607 100644
--- a/test/source/tests/flaky.ts
+++ b/test/source/tests/flaky.ts
@@ -80,6 +80,7 @@ export const defineFlakyTests = (testVariant: TestVariant, testWithBrowser: Test
         // Updating the key to valid one
         const updatePrvPage = await settingsPage.getFrame(['my_key.htm'], { timeout: 5 });
         await updatePrvPage.waitAndClick('@action-update-prv');
+        await updatePrvPage.waitAndClick('@source-paste');
         await updatePrvPage.waitAndType('@input-prv-key', validKey);
         await updatePrvPage.type('@input-passphrase', 'qweasd');
         await updatePrvPage.waitAndClick('@action-update-key');
diff --git a/test/source/tests/settings.ts b/test/source/tests/settings.ts
index 54a3b9e2357..5687d701bbf 100644
--- a/test/source/tests/settings.ts
+++ b/test/source/tests/settings.ts
@@ -15,7 +15,7 @@ import { SetupPageRecipe } from './page-recipe/setup-page-recipe';
 import { testConstants } from './tooling/consts';
 import { PageRecipe } from './page-recipe/abstract-page-recipe';
 import { OauthPageRecipe } from './page-recipe/oauth-page-recipe';
-import { KeyInfoWithIdentity, KeyUtil } from '../core/crypto/key';
+import { KeyInfoWithIdentity, KeyUtil, PubkeyInfoWithLastCheck } from '../core/crypto/key';
 import { Buf } from '../core/buf';
 import { GoogleData } from '../mock/google/google-data';
 import Parse from './../util/parse';
@@ -915,6 +915,7 @@ export const defineSettingsTests = (testVariant: TestVariant, testWithBrowser: T
         await Util.sleep(1);
         await myKeyFrame.waitAll('@content-fingerprint');
         await myKeyFrame.waitAndClick('@action-update-prv');
+        await myKeyFrame.waitAndClick('@source-paste');
         await myKeyFrame.waitAndType('@input-prv-key', testConstants.testKeyMultiple98acfa1eadab5b92);
         await myKeyFrame.type('@input-passphrase', '1234');
         await myKeyFrame.waitAndClick('@action-update-key');
@@ -929,6 +930,87 @@ export const defineSettingsTests = (testVariant: TestVariant, testWithBrowser: T
         await settingsPage.close();
       })
     );
+    test(
+      'settings - my key page - update private key from file',
+      testWithBrowser(async (t, browser) => {
+        const acctEmail = 'flowcrypt.test.key.multiple@gmail.com';
+        t.context.mockApi!.configProvider = new ConfigurationProvider({
+          attester: {
+            pubkeyLookup: {},
+          },
+        });
+        const dbPage = await browser.newExtensionPage(t, 'chrome/dev/ci_unit_test.htm');
+        const settingsPage = await BrowserRecipe.openSettingsLoginApprove(t, browser, acctEmail);
+        await SetupPageRecipe.manualEnter(
+          settingsPage,
+          'unused',
+          {
+            submitPubkey: false,
+            usedPgpBefore: false,
+            key: {
+              title: '?',
+              // eslint-disable-next-line no-null/no-null
+              armored: null,
+              filePath: 'test/samples/openpgp/flowcrypttestkeymultiplegmailcom-0x98acfa1eadab5b92-original.asc',
+              passphrase: '1234',
+              longid: '1b383d0334e38b28',
+            },
+          },
+          { isSavePassphraseChecked: false, isSavePassphraseHidden: false }
+        );
+        // test the pubkey in the storage
+        const oldContact = await dbPage.page.evaluate(async acctEmail => {
+          // eslint-disable-next-line @typescript-eslint/no-explicit-any, @typescript-eslint/no-unsafe-return
+          return await (window as any).ContactStore.getOneWithAllPubkeys(undefined, acctEmail);
+        }, acctEmail);
+        expect(oldContact.sortedPubkeys.length).to.equal(1);
+        expect((oldContact.sortedPubkeys as PubkeyInfoWithLastCheck[])[0].pubkey.lastModified).to.equal(1610024667000);
+        await SettingsPageRecipe.toggleScreen(settingsPage, 'additional');
+        const myKeyFrame = await SettingsPageRecipe.awaitNewPageFrame(settingsPage, `@action-show-key-0`, ['my_key.htm', 'placement=settings']);
+        await Util.sleep(1);
+        await myKeyFrame.waitAll('@content-fingerprint');
+        await myKeyFrame.waitAndClick('@action-update-prv');
+        {
+          const [fileChooser] = await Promise.all([settingsPage.page.waitForFileChooser(), myKeyFrame.waitAndClick('@source-file', { retryErrs: true })]);
+          await fileChooser.accept(['test/samples/openpgp/flowcrypttestkeymultiplegmailcom-0x98acfa1eadab5b92-updated-userid-issue.key']); // binary key
+        }
+        await myKeyFrame.type('@input-passphrase', '1234');
+        await myKeyFrame.waitAndClick('@action-update-key');
+        await PageRecipe.waitForModalAndRespond(myKeyFrame, 'error', {
+          contentToCheck: 'The set of User IDs in this key is not supported.',
+          clickOn: 'confirm',
+        });
+        // test the pubkey in the storage
+        const expectedOldContact = await dbPage.page.evaluate(async acctEmail => {
+          // eslint-disable-next-line @typescript-eslint/no-explicit-any, @typescript-eslint/no-unsafe-return
+          return await (window as any).ContactStore.getOneWithAllPubkeys(undefined, acctEmail);
+        }, acctEmail);
+        expect(expectedOldContact.sortedPubkeys.length).to.equal(1);
+        expect((expectedOldContact.sortedPubkeys as PubkeyInfoWithLastCheck[])[0].pubkey.lastModified).to.equal(1610024667000);
+        {
+          const [fileChooser] = await Promise.all([settingsPage.page.waitForFileChooser(), myKeyFrame.waitAndClick('@source-file', { retryErrs: true })]);
+          await fileChooser.accept(['test/samples/openpgp/flowcrypttestkeymultiplegmailcom-0x98acfa1eadab5b92-updated.key']); // binary key
+        }
+        await myKeyFrame.waitAndClick('@action-update-key');
+        await PageRecipe.waitForModalAndRespond(myKeyFrame, 'confirm', {
+          contentToCheck: 'Public and private key updated locally',
+          clickOn: 'cancel',
+        });
+        // test the pubkey in the storage
+        const newContact = await dbPage.page.evaluate(async acctEmail => {
+          // eslint-disable-next-line @typescript-eslint/no-explicit-any, @typescript-eslint/no-unsafe-return
+          return await (window as any).ContactStore.getOneWithAllPubkeys(undefined, acctEmail);
+        }, acctEmail);
+        expect(newContact.sortedPubkeys.length).to.equal(1);
+        const newPubkey = (newContact.sortedPubkeys as PubkeyInfoWithLastCheck[])[0].pubkey;
+        expect(newPubkey.lastModified).to.equal(1689250647000);
+        // we now have two uids
+        expect(newPubkey.identities).to.eql(['Additional Name <flowcrypt.test@example.com>', 'flowcrypt.test.key.multiple@gmail.com']);
+        expect(newPubkey.emails).to.eql(['flowcrypt.test@example.com', 'flowcrypt.test.key.multiple@gmail.com']);
+        await settingsPage.close();
+        await dbPage.close();
+      })
+    );
     test(
       'settings - my key page - revocation certificate',
       testWithBrowser(async (t, browser) => {
@@ -1462,6 +1544,7 @@ export const defineSettingsTests = (testVariant: TestVariant, testWithBrowser: T
         await Util.sleep(1);
         await myKeyFrame.waitAll('@content-fingerprint');
         await myKeyFrame.waitAndClick('@action-update-prv');
+        await myKeyFrame.waitAndClick('@source-paste');
         await myKeyFrame.waitAndType('@input-prv-key', testConstants.testKeyB8F687BCDE14435A);
         await myKeyFrame.type('@input-passphrase', passphrase);
         await myKeyFrame.waitAndClick('@action-update-key');
