diff --git a/extension/css/webmail.css b/extension/css/webmail.css
index eede1d13e4d..b07448fe347 100644
--- a/extension/css/webmail.css
+++ b/extension/css/webmail.css
@@ -29,6 +29,10 @@
   outline: 0;
 }
 
+.btDi4d {
+  position: initial !important;
+}
+
 .small #flowcrypt_secure_compose_button_icon {
   height: 40px;
 }
@@ -190,8 +194,7 @@ body.cryptup_gmail .inserted div.reply_message_button {
   display: inline-flex;
   padding: 20px 12px 0 10px;
   opacity: 0.75;
-  margin-left: 18px;
-  margin-right: 8px;
+  margin: 0;
   height: auto;
 }
 
@@ -207,7 +210,11 @@ body.cryptup_gmail div.action_menu_message_button {
   align-items: center;
   text-transform: capitalize;
   cursor: pointer;
-  padding: 4px;
+  padding: 8px 4px;
+  font-size: 14px;
+  font-weight: 400;
+  color: #1f1f1f;
+  line-height: 16px;
 }
 
 body.cryptup_gmail div.action_menu_message_button:hover {
@@ -215,9 +222,9 @@ body.cryptup_gmail div.action_menu_message_button:hover {
 }
 
 body.cryptup_gmail div.action_menu_message_button > img {
-  height: 20px;
-  width: 20px;
-  padding: 0 12px;
+  height: auto;
+  width: 18px;
+  padding: 0 11px;
   object-fit: contain;
 }
 
diff --git a/extension/js/content_scripts/webmail/gmail/gmail-element-replacer.ts b/extension/js/content_scripts/webmail/gmail/gmail-element-replacer.ts
index 56b6979546f..36c01f418d5 100644
--- a/extension/js/content_scripts/webmail/gmail/gmail-element-replacer.ts
+++ b/extension/js/content_scripts/webmail/gmail/gmail-element-replacer.ts
@@ -56,8 +56,8 @@ export class GmailElementReplacer extends WebmailElementReplacer {
     msgInner: 'div.a3s:visible:not(.undefined), .message_inner_body:visible',
     msgInnerText: 'table.cf.An',
     msgInnerContainingPgp: "div.a3s:not(.undefined):contains('" + PgpArmor.headers('null').begin + "')",
-    msgActionsBtn: '.J-J5-Ji.aap',
-    msgActionsMenu: '.b7.J-M',
+    msgActionsBtn: '.Wsq5Cf',
+    msgActionsMenu: '.tB5Jxf-M-S5Cmsd, ul.aqdrmf-Kf[role="menu"]',
     attachmentsContainerOuter: 'div.hq.gt',
     attachmentsContainerInner: 'div.aQH',
     translatePrompt: '.adI, .wl4W9b',
@@ -67,7 +67,7 @@ export class GmailElementReplacer extends WebmailElementReplacer {
     standardComposeRecipient: 'div.az9 span[email][data-hovercard-id]',
     numberOfAttachments: '.aVW',
     numberOfAttachmentsLabel: '.aVW span:first-child',
-    attachmentsButtons: '.aZi',
+    downloadAllAttachmentsButton: '.aZi, .pYTkkf-JX-ano',
     draftsList: '.ae4',
   };
 
@@ -297,8 +297,8 @@ export class GmailElementReplacer extends WebmailElementReplacer {
     return !!$('iframe.pgp_block').filter(':visible').length;
   };
 
-  private addMenuButton = (replyOption: ReplyOption, gmailContextMenuBtn: string) => {
-    if ($(gmailContextMenuBtn).is(':visible') && !document.querySelector(`.action_${replyOption.replace('a_', '')}_message_button`)) {
+  private addMenuButton = (replyOption: ReplyOption, gmailContextMenuBtn: Element | null) => {
+    if (gmailContextMenuBtn && $(gmailContextMenuBtn).is(':visible') && !document.querySelector(`.action_${replyOption.replace('a_', '')}_message_button`)) {
       const button = $(this.factory.btnSecureMenuBtn(replyOption)).insertAfter(gmailContextMenuBtn); // xss-safe-factory
       button.on(
         'click',
@@ -323,7 +323,7 @@ export class GmailElementReplacer extends WebmailElementReplacer {
       // only replace the last one FlowCrypt reply button if does not have any buttons replaced yet, and only replace the last one
       for (const elem of convoReplyBtnsArr) {
         $(elem).addClass('inserted');
-        const gmailReplyBtn = $(elem).find('.aaq.L3');
+        const gmailReplyBtn = $(elem).find('.DILLkc');
         const secureReplyBtn = $(this.factory.btnSecureReply()).insertAfter(gmailReplyBtn); // xss-safe-factory
         secureReplyBtn.addClass(gmailReplyBtn.attr('class') || '');
         secureReplyBtn.off();
@@ -391,7 +391,7 @@ export class GmailElementReplacer extends WebmailElementReplacer {
       return;
     }
     // eslint-disable-next-line @typescript-eslint/no-non-null-assertion
-    const messageContainer = secureReplyInvokedFromMenu ? $('.T-I-JO.T-I-Kq').closest('.h7') : $(btn.closest('.h7')!);
+    const messageContainer = secureReplyInvokedFromMenu ? $('.ii.gt').closest('div.h7') : $(btn.closest('.h7')!);
     if (messageContainer.is(':last-child')) {
       if (this.isEncrypted()) {
         await this.setReplyBoxEditable(replyOption);
@@ -402,8 +402,7 @@ export class GmailElementReplacer extends WebmailElementReplacer {
       this.insertEncryptedReplyBox(messageContainer, replyOption);
     }
     if (secureReplyInvokedFromMenu) {
-      $(this.sel.msgActionsBtn).removeClass('T-I-JO T-I-Kq');
-      $(this.sel.msgActionsMenu).hide();
+      $(this.sel.msgActionsBtn).trigger('click');
     }
   };
 
@@ -559,7 +558,7 @@ export class GmailElementReplacer extends WebmailElementReplacer {
     }
     if (nRenderedAttachments !== attachments.length) {
       // according to #4200, no point in showing "download all" button if at least one attachment is encrypted etc.
-      $(this.sel.attachmentsButtons).hide();
+      $(this.sel.downloadAllAttachmentsButton).hide();
     }
     if (nRenderedAttachments === 0) {
       attachmentsContainerInner.parents(this.sel.attachmentsContainerOuter).first().hide();
@@ -638,7 +637,23 @@ export class GmailElementReplacer extends WebmailElementReplacer {
   };
 
   private getConvoRootEl = (anyInnerElement: HTMLElement) => {
-    return $(anyInnerElement).closest('div.if, div.aHU, td.Bu').first();
+    const ancestorConvoRoot = $(anyInnerElement).closest('div.if, div.aHU, td.Bu');
+    if (ancestorConvoRoot.length) {
+      return ancestorConvoRoot.first();
+    }
+
+    // New Gmail structure: conversation root might be a sibling
+    // Navigate to common parent container and find conversation root
+    const commonParent = $(anyInnerElement).closest('.nH.a98.iY, .if');
+    if (commonParent.length) {
+      const siblingConvoRoot = commonParent.find('div.if, div.aHU, td.Bu').first();
+      if (siblingConvoRoot.length) {
+        return siblingConvoRoot;
+      }
+    }
+
+    // Fallback: return empty jQuery object to maintain consistent return type
+    return $();
   };
 
   private insertEncryptedReplyBox = (messageContainer: JQuery<Element>, replyOption: ReplyOption) => {
@@ -655,7 +670,7 @@ export class GmailElementReplacer extends WebmailElementReplacer {
 
   private replaceStandardReplyBox = async (msgId?: string, force = false) => {
     const legacyDraftReplyRegex = new RegExp(/\[(flowcrypt|cryptup):link:draft_reply:([0-9a-fr\-]+)]/);
-    const newReplyBoxes = $('div.nr.tMHS5d, td.amr > div.nr, div.gA td.I5').not('.reply_message_evaluated').filter(':visible').get();
+    const newReplyBoxes = $('div.nr.tMHS5d, div.gA td.I5, .amr > div.nr').not('.reply_message_evaluated').filter(':visible').get();
     if (newReplyBoxes.length) {
       // removing this line will cause unexpected draft creation bug reappear
       // https://github.com/FlowCrypt/flowcrypt-browser/issues/5616#issuecomment-1972897692
@@ -946,27 +961,41 @@ export class GmailElementReplacer extends WebmailElementReplacer {
      *
      * Issue: https://github.com/FlowCrypt/flowcrypt-browser/issues/5933
      */
-    const messageContainer = $('.T-I-JO.T-I-Kq').closest('.h7');
+    // Find the active message menu
+    const visibleMenu = Array.from(document.querySelectorAll(this.sel.msgActionsMenu)).find(
+      menu => window.getComputedStyle(menu).display !== 'none' && (menu as HTMLElement).offsetParent
+    );
+    if (!visibleMenu) {
+      return;
+    }
+
+    // Find the message container from the menu's position or context
+    const messageContainer = $('div.h7:visible').last(); // Get the last visible message container
     const msgIdElement = messageContainer.find('[data-legacy-message-id], [data-message-id]');
     const msgId = msgIdElement.attr('data-legacy-message-id') || msgIdElement.attr('data-message-id');
-    const replyAllMenuButton = document.querySelector('#r2');
+
+    // New Gmail uses data-action-type attributes
+    const replyButton = visibleMenu.querySelector('li[data-action-type="94"]');
+    const forwardButton = visibleMenu.querySelector('li[data-action-type="25"]');
+    const replyAllButton = visibleMenu.querySelector('li[data-action-type="24"]'); // Estimated based on pattern
+
     // Cannot use jQuery $('#r2').is(':visible') because the element is considered invisible if its parent has display: none.
-    if (replyAllMenuButton && window.getComputedStyle(replyAllMenuButton).display !== 'none') {
-      this.addMenuButton('a_reply_all', '#r2');
+    if (replyAllButton && window.getComputedStyle(replyAllButton).display !== 'none') {
+      this.addMenuButton('a_reply_all', replyAllButton);
     } else if (msgId) {
       try {
         const gmailMsg = await this.emailProvider.msgGet(msgId, 'metadata');
         const replyMeta = GmailParser.determineReplyMeta(this.acctEmail, [], gmailMsg);
 
         if (replyMeta.to.length > 1) {
-          this.addMenuButton('a_reply_all', '#r');
+          this.addMenuButton('a_reply_all', replyButton);
         }
       } catch (error) {
         console.error(`Failed to retrieve message metadata for ID ${msgId}:`, error);
       }
     }
 
-    this.addMenuButton('a_reply', '#r');
-    this.addMenuButton('a_forward', '#r3');
+    this.addMenuButton('a_reply', replyButton);
+    this.addMenuButton('a_forward', forwardButton);
   };
 }
diff --git a/package-lock.json b/package-lock.json
index 21de99fd717..707fb74cfa9 100644
--- a/package-lock.json
+++ b/package-lock.json
@@ -1798,18 +1798,6 @@
         "libqp": "2.1.1"
       }
     },
-    "node_modules/@zone-eu/mailsplit": {
-      "version": "5.4.7",
-      "resolved": "https://registry.npmjs.org/@zone-eu/mailsplit/-/mailsplit-5.4.7.tgz",
-      "integrity": "sha512-jApX86aDgolMz08pP20/J2zcns02NSK3zSiYouf01QQg4250L+GUAWSWicmS7eRvs+Z7wP7QfXrnkaTBGrIpwQ==",
-      "dev": true,
-      "license": "(MIT OR EUPL-1.1+)",
-      "dependencies": {
-        "libbase64": "1.3.0",
-        "libmime": "5.3.7",
-        "libqp": "2.1.1"
-      }
-    },
     "node_modules/@zxcvbn-ts/core": {
       "version": "3.0.4",
       "resolved": "https://registry.npmjs.org/@zxcvbn-ts/core/-/core-3.0.4.tgz",
diff --git a/test/source/tests/gmail.ts b/test/source/tests/gmail.ts
index 070308c19a7..8c5f5bea769 100644
--- a/test/source/tests/gmail.ts
+++ b/test/source/tests/gmail.ts
@@ -180,7 +180,7 @@ export const defineGmailTests = (testVariant: TestVariant, testWithBrowser: Test
         await gotoGmailPage(gmailPage, '/KtbxLvHkSWwbVHxgCbWNvXVKGjFgqMbGQq');
         await Util.sleep(5);
         await gmailPage.waitAll('iframe');
-        await gmailPage.waitAll(['.aZi'], { visible: true });
+        await gmailPage.waitAll(['.pYTkkf-JX-ano'], { visible: true });
 
         // attachments which contain emoji in filename are rendered correctly
         await gotoGmailPage(gmailPage, '/FMfcgzGtwqFGhMwWtLRjkPJlQlZHSlrW');
@@ -190,7 +190,7 @@ export const defineGmailTests = (testVariant: TestVariant, testWithBrowser: Test
         const urls2 = await gmailPage.getFramesUrls(['/chrome/elements/attachment.htm']);
         expect(urls2.length).to.equal(2);
         expect(await gmailPage.waitForContent('.aVW span:first-child', '2'));
-        expect(await gmailPage.waitForContent('.aVW span.a2H', ' •  Scanned by Gmail'));
+        expect(await gmailPage.waitForContent('.aVW span.a2H', '  •  Scanned by Gmail'));
         await gmailPage.close();
       })
     );
@@ -405,10 +405,10 @@ export const defineGmailTests = (testVariant: TestVariant, testWithBrowser: Test
       testWithBrowser(async (t, browser) => {
         await BrowserRecipe.setUpCommonAcct(t, browser, 'ci.tests.gmail');
         let gmailPage = await openGmailPage(t, browser, '/FMfcgzGkbDRNgcQxLmkhBCKVSFwkfdvV'); // plain convo
-        await gmailPage.waitAndClick('[data-tooltip="Reply"]', { delay: 1 });
+        await gmailPage.waitAndClick('div.adn [aria-label="Reply"]', { delay: 1 });
         await gmailPage.close();
         gmailPage = await openGmailPage(t, browser, '/181d226b4e69f172'); // go to encrypted convo
-        await gmailPage.waitAndClick('[data-tooltip="Reply"]', { delay: 1 });
+        await gmailPage.waitAndClick('div.adn [aria-label="Reply"]', { delay: 1 });
         await gmailPage.waitTillGone('.reply_message');
         await gmailPage.waitAll('[data-tooltip^="Send"]'); // The Send button from the Standard reply box
         await gmailPage.waitForContent(
@@ -419,7 +419,7 @@ export const defineGmailTests = (testVariant: TestVariant, testWithBrowser: Test
         await gmailPage.waitAll('.reply_message');
         await pageHasSecureReplyContainer(t, browser, gmailPage, { isReplyPromptAccepted: true });
         await gotoGmailPage(gmailPage, '/FMfcgzGkbDRNpjDdNvCrwzqvXspZZxvh'); // go to signed convo
-        await gmailPage.waitAndClick('[data-tooltip="Reply"]', { delay: 1 });
+        await gmailPage.waitAndClick('div.adn [aria-label="Reply"]', { delay: 1 });
         await gmailPage.waitTillGone('.reply_message');
         await gmailPage.waitAll('[data-tooltip^="Send"]'); // The Send button from the Standard reply box
         await gmailPage.notPresent('.reply_message_evaluated .error_notification'); // should not show the warning about switching to encrypted reply
@@ -438,7 +438,7 @@ export const defineGmailTests = (testVariant: TestVariant, testWithBrowser: Test
           await gmailPage.waitAndClick('[role="listitem"] .adf.ads', { delay: 1 }); // click first message of thread
           await Util.sleep(3);
           const messages = await gmailPage.target.$$('[role="listitem"] .adn.ads');
-          const plainReplyButton = await messages[0].$('[data-tooltip="Reply"]');
+          const plainReplyButton = await messages[0].$('[aria-label="Reply"]');
           await Util.sleep(1);
           await plainReplyButton!.click();
           await gmailPage.waitAndClick('#switch_to_encrypted_reply'); // Switch to encrypted compose
@@ -467,7 +467,7 @@ export const defineGmailTests = (testVariant: TestVariant, testWithBrowser: Test
         const messages = await gmailPage.target.$$('[role="listitem"] .adn.ads');
         expect(messages.length).to.equal(2);
 
-        const plainReplyButton = await messages[0].$('[data-tooltip="Reply"]');
+        const plainReplyButton = await messages[0].$('[aria-label="Reply"]');
         expect(plainReplyButton).to.be.ok;
         await Util.sleep(1);
         await plainReplyButton!.click();
@@ -491,11 +491,11 @@ export const defineGmailTests = (testVariant: TestVariant, testWithBrowser: Test
         await BrowserRecipe.setUpCommonAcct(t, browser, 'ci.tests.gmail');
         const gmailPage = await openGmailPage(t, browser);
         await gotoGmailPage(gmailPage, '/FMfcgzGkbDRNgcQxLmkhBCKVSFwkfdvV'); // plain convo
-        await gmailPage.waitAndClick('[data-tooltip="Reply"]', { delay: 1 });
+        await gmailPage.waitAndClick('div.adn [aria-label="Reply"]', { delay: 1 });
         await gotoGmailPage(gmailPage, '/FMfcgzGtwgfMhWTlgRwwKWzRhqNZzwXz'); // go to encrypted convo
         await Util.sleep(5);
-        await gmailPage.waitAndClick('.adn [data-tooltip="More"]', { delay: 1 });
-        await gmailPage.waitAndClick('[act="24"]', { delay: 1 }); // click reply-all
+        await gmailPage.waitAndClick('.adn [aria-label="More message options"]', { delay: 1 });
+        await gmailPage.waitAndClick('li[data-action-type="24"]', { delay: 1 }); // click reply-all
         await Util.sleep(3);
         await gmailPage.waitAll('[data-tooltip^="Send"]'); // The Send button from the Standard reply box
         await gmailPage.waitForContent(
@@ -518,7 +518,7 @@ export const defineGmailTests = (testVariant: TestVariant, testWithBrowser: Test
         await BrowserRecipe.setUpCommonAcct(t, browser, 'ci.tests.gmail');
         const gmailPage = await openGmailPage(t, browser);
         await gotoGmailPage(gmailPage, '/FMfcgzQZTMHNLflWQjRcSvWlMsKbLhpr');
-        await gmailPage.waitAndClick('.adn [data-tooltip="More"]', { delay: 1 });
+        await gmailPage.waitAndClick('.adn [aria-label="More message options"]', { delay: 1 });
         await gmailPage.waitAll('.action_reply_all_message_button');
       })
     );
@@ -531,8 +531,8 @@ export const defineGmailTests = (testVariant: TestVariant, testWithBrowser: Test
           const gmailPage = await openGmailPage(t, browser);
           await gotoGmailPage(gmailPage, '/FMfcgzGtwgfMhWTlgRwwKWzRhqNZzwXz'); // go to encrypted convo
           await Util.sleep(5);
-          await gmailPage.waitAndClick('.adn [data-tooltip="More"]', { delay: 1 });
-          await gmailPage.waitAndClick('[act="25"]', { delay: 1 }); // click forward
+          await gmailPage.waitAndClick('.adn [aria-label="More message options"]', { delay: 1 });
+          await gmailPage.waitAndClick('li[data-action-type="25"]', { delay: 1 }); // click forward
           await Util.sleep(3);
           await gmailPage.waitAll('[data-tooltip^="Send"]'); // The Send button from the Standard reply box
           await gmailPage.waitForContent(
@@ -556,7 +556,7 @@ export const defineGmailTests = (testVariant: TestVariant, testWithBrowser: Test
         await BrowserRecipe.setUpCommonAcct(t, browser, 'ci.tests.gmail');
         const gmailPage = await openGmailPage(t, browser);
         await gotoGmailPage(gmailPage, '/FMfcgzGtwgfMhWTlgRwwKWzRhqNZzwXz'); // go to encrypted convo
-        const gmailContextMenu = '.J-J5-Ji.aap';
+        const gmailContextMenu = '.adn [aria-label="More message options"]';
         await gmailPage.waitAndClick(gmailContextMenu);
         await Util.sleep(1);
         expect(await gmailPage.isElementPresent('@action-reply-message-button'));
@@ -589,7 +589,7 @@ export const defineGmailTests = (testVariant: TestVariant, testWithBrowser: Test
           const threadId = '181d226b4e69f172'; // 1st message -- thread id
           const gmailPage = await openGmailPage(t, browser, `/${threadId}`);
           await GmailPageRecipe.trimConvo(gmailPage, threadId);
-          await gmailPage.waitAndClick('[data-tooltip="Reply"]', { delay: 5 });
+          await gmailPage.waitAndClick('div.adn [aria-label="Reply"]', { delay: 5 });
           t.timeout(minutes(2)); // extend ava's timeout
           await Util.sleep(5);
           await gmailPage.waitTillFocusIsIn('div[aria-label="Message Body"]', { timeout: 10 });
@@ -621,7 +621,7 @@ export const defineGmailTests = (testVariant: TestVariant, testWithBrowser: Test
         await Util.sleep(5);
         await gmailPage.waitAll('iframe');
         expect(await gmailPage.isElementPresent('@container-attachments')).to.equal(false);
-        await gmailPage.waitAll(['.aZi'], { visible: false });
+        await gmailPage.waitAll(['.pYTkkf-JX-ano'], { visible: false });
         expect(await gmailPage.isElementVisible('.aQH')).to.equal(false); // original attachment container(s) should be hidden
         await gmailPage.close();
       })
@@ -642,7 +642,7 @@ export const defineGmailTests = (testVariant: TestVariant, testWithBrowser: Test
         await Util.sleep(5);
         await gmailPage.waitAll('iframe');
         expect(await gmailPage.isElementPresent('@container-attachments')).to.equal(false);
-        await gmailPage.waitAll(['.aZi'], { visible: false });
+        await gmailPage.waitAll(['.pYTkkf-JX-ano'], { visible: false });
         await gmailPage.close();
       })
     );
diff --git a/test/source/tests/setup.ts b/test/source/tests/setup.ts
index f0b40120f9f..ddea1b21bbf 100644
--- a/test/source/tests/setup.ts
+++ b/test/source/tests/setup.ts
@@ -853,6 +853,7 @@ AN8G3r5Htj8olot+jm9mIa5XLXWzMNUZgg==
         await addKeyPopup.waitAndClick('.action_add_private_key', { delay: 1 });
         await Util.sleep(1);
         await gmailPage.page.reload();
+        await Util.sleep(3);
         await gmailPage.waitTillGone('@webmail-notification-notify_expiring_keys');
         // remove added key and observe warning appears again
         await settingsPage.waitAndClick('@action-remove-key-1');