diff --git a/extension/chrome/settings/index.ts b/extension/chrome/settings/index.ts
index 40128469777..c2342edd23a 100644
--- a/extension/chrome/settings/index.ts
+++ b/extension/chrome/settings/index.ts
@@ -496,24 +496,67 @@ View.run(
     private addKeyRowsHtml = async (privateKeys: KeyInfoWithIdentity[]) => {
       let html = '';
       const canRemoveKey = !this.clientConfiguration?.usesKeyManager();
+
+      // 1. Parse and prepare data
+      const rows = [];
       for (let i = 0; i < privateKeys.length; i++) {
         const ki = privateKeys[i];
         const prv = await KeyUtil.parse(ki.private);
         const created = new Date(prv.created);
         const date = Str.monthName(created.getMonth()) + ' ' + created.getDate() + ', ' + created.getFullYear();
+        const isExpired = KeyUtil.expired(prv);
+        rows.push({
+          ki,
+          prv,
+          createdTime: prv.created,
+          dateStr: date,
+          isExpired,
+          originalIndex: i,
+        });
+      }
+
+      // 2. Sort: newest to oldest
+      rows.sort((a, b) => b.createdTime - a.createdTime);
+
+      // 3. Build HTML
+      // Header row
+      html += `
+        <div class="row key-list-header" style="font-weight: 600; padding: 10px 0; border-bottom: 2px solid #eee;">
+          <div class="col-3">Email</div>
+          <div class="col-2">Created</div>
+          <div class="col-6">Fingerprint</div>
+          <div class="col-1">Status</div>
+        </div>
+      `;
+
+      for (const row of rows) {
+        const { ki, prv, dateStr, isExpired, originalIndex } = row;
+
         let removeKeyBtn = '';
         if (canRemoveKey && privateKeys.length > 1) {
-          removeKeyBtn = `(<a href="#" class="action_remove_key" data-test="action-remove-key-${i}" data-fingerprint=${ki.fingerprints[0]} data-type="${ki.family}" data-id="${ki.id}" data-longid="${ki.longid}">remove</a>)`;
+          removeKeyBtn = `<a href="#" class="action_remove_key" style="margin-left: 5px;" data-test="action-remove-key-${originalIndex}" data-fingerprint=${ki.fingerprints[0]} data-type="${ki.family}" data-id="${ki.id}" data-longid="${ki.longid}">remove</a>`;
         }
+
         const escapedEmail = Xss.escape(prv.emails[0] || '');
-        const escapedLink = `<a href="#" data-test="action-show-key-${i}" class="action_show_key" page="modules/my_key.htm" addurltext="&fingerprint=${ki.id}">${escapedEmail}</a>`;
-        const fpHtml = `fingerprint:&nbsp;<span class="good">${Str.spaced(Xss.escape(ki.fingerprints[0]))}</span>`;
-        const space = `&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;`;
-        html += `<div class="row key-content-row">`;
-        html += `  <div class="col-12">${escapedLink} from ${Xss.escape(date)}${space}${fpHtml}${space}${KeyUtil.statusHtml(ki.id, prv)}${space}${removeKeyBtn}</div>`;
+        const escapedLink = `<a href="#" data-test="action-show-key-${originalIndex}" class="action_show_key" page="modules/my_key.htm" addurltext="&fingerprint=${ki.id}">${escapedEmail}</a>`;
+        const fpHtml = `<span class="good" style="font-family: monospace;">${Str.spaced(Xss.escape(ki.fingerprints[0]))}</span>`;
+
+        const rowClass = isExpired ? 'key-content-row expired' : 'key-content-row';
+        const opacityStyle = isExpired ? 'opacity: 0.7;' : '';
+
+        html += `<div class="row ${rowClass}" style="padding: 10px 0; border-bottom: 1px solid #e6e6e6; align-items: center; ${opacityStyle}">`;
+        html += `  <div class="col-3" style="overflow: hidden; text-overflow: ellipsis;">${escapedLink}</div>`;
+        html += `  <div class="col-2">${Xss.escape(dateStr)}</div>`;
+        html += `  <div class="col-6">${fpHtml}</div>`;
+        html += `  <div class="col-1" style="display: flex; justify-content: space-between; align-items: center;">
+                     ${KeyUtil.statusHtml(ki.id, prv)}
+                     ${removeKeyBtn}
+                   </div>`;
         html += `</div>`;
       }
+
       Xss.sanitizeAppend('.key_list', html);
+
       $('.action_show_key').on(
         'click',
         this.setHandler(async target => {
diff --git a/extension/css/settings.css b/extension/css/settings.css
index 1afaa0c5849..47ec9699932 100644
--- a/extension/css/settings.css
+++ b/extension/css/settings.css
@@ -533,7 +533,7 @@ body#settings .settings-border .row {
 }
 
 body#settings .settings-border .key-content-row {
-  padding: 7px 0;
+  padding: 4px 0;
   border-bottom: 1px solid #e6e6e6;
 }
 
@@ -544,6 +544,10 @@ body#settings .settings-border .key_list {
   height: 219px;
 }
 
+.key-content-row.expired {
+  opacity: 0.7;
+}
+
 #settings-row .box img.security-icon {
   width: 70px;
 }
@@ -847,4 +851,4 @@ span.fc-badge {
 .fc-badge-light-gray {
   background-color: #bcbcbc;
   color: #444 !important;
-}
+}
\ No newline at end of file
diff --git a/test/source/tests/setup.ts b/test/source/tests/setup.ts
index ddea1b21bbf..720618cefa0 100644
--- a/test/source/tests/setup.ts
+++ b/test/source/tests/setup.ts
@@ -851,7 +851,7 @@ AN8G3r5Htj8olot+jm9mIa5XLXWzMNUZgg==
         await addKeyPopup.waitAndType('@input-armored-key', updatedKey.privateKey);
         await addKeyPopup.waitAndType('#input_passphrase', passphrase);
         await addKeyPopup.waitAndClick('.action_add_private_key', { delay: 1 });
-        await Util.sleep(1);
+        await settingsPage.waitAll('@action-show-key-1');
         await gmailPage.page.reload();
         await Util.sleep(3);
         await gmailPage.waitTillGone('@webmail-notification-notify_expiring_keys');
@@ -2250,7 +2250,7 @@ AN8G3r5Htj8olot+jm9mIa5XLXWzMNUZgg==
         const title = await settingsPage.read('@container-overlay-prompt-text');
         expect(title).to.contain(
           'Failed to store newly generated key on FlowCrypt Email Key Manager, ' +
-            'No key has been generated for reject.client.keypair@key-manager-autogen.flowcrypt.test yet. Please ask your administrator.'
+          'No key has been generated for reject.client.keypair@key-manager-autogen.flowcrypt.test yet. Please ask your administrator.'
         );
         await settingsPage.click('@action-show-overlay-details');
         await settingsPage.waitAll('@container-overlay-details');
@@ -2258,7 +2258,7 @@ AN8G3r5Htj8olot+jm9mIa5XLXWzMNUZgg==
         const details = await settingsPage.read('@container-overlay-details');
         expect(details).to.contain(
           `405 when PUT-ing https://localhost:${t.context.urls?.port}/flowcrypt-email-key-manager/v1/keys/private string: ` +
-            'privateKey -> No key has been generated for reject.client.keypair@key-manager-autogen.flowcrypt.test yet'
+          'privateKey -> No key has been generated for reject.client.keypair@key-manager-autogen.flowcrypt.test yet'
         );
         expect(details).to.not.contain('PRIVATE KEY');
       })