diff --git a/webapp/channels/src/components/admin_console/admin_definition.tsx b/webapp/channels/src/components/admin_console/admin_definition.tsx
index 14890f118c..68b696f100 100644
--- a/webapp/channels/src/components/admin_console/admin_definition.tsx
+++ b/webapp/channels/src/components/admin_console/admin_definition.tsx
@@ -6318,7 +6318,7 @@ const AdminDefinition: AdminDefinitionType = {
                             type: 'dropdown',
                             key: 'ExperimentalSettings.ClientSideCertCheck',
                             label: defineMessage({id: 'admin.experimental.clientSideCertCheck.title', defaultMessage: 'Client-Side Certification Login Method:'}),
-                            help_text: defineMessage({id: 'admin.experimental.clientSideCertCheck.desc', defaultMessage: 'When **primary**, after the client side certificate is verified, user’s email is retrieved from the certificate and is used to log in without a password. When **secondary**, after the client side certificate is verified, user’s email is retrieved from the certificate and matched against the one supplied by the user. If they match, the user logs in with regular email/password credentials.'}),
+                            help_text: defineMessage({id: 'admin.experimental.clientSideCertCheck.desc', defaultMessage: "When **primary**, after the client side certificate is verified, user's email is retrieved from the certificate and is used to log in without a password. When **secondary**, after the client side certificate is verified, user's email is retrieved from the certificate and matched against the one supplied by the user. If they match, the user logs in with regular email/password credentials."}),
                             help_text_markdown: true,
                             options: [
                                 {
@@ -6518,7 +6518,7 @@ const AdminDefinition: AdminDefinitionType = {
                             type: 'number',
                             key: 'TeamSettings.UserStatusAwayTimeout',
                             label: defineMessage({id: 'admin.experimental.userStatusAwayTimeout.title', defaultMessage: 'User Status Away Timeout:'}),
-                            help_text: defineMessage({id: 'admin.experimental.userStatusAwayTimeout.desc', defaultMessage: 'This setting defines the number of seconds after which the user’s status indicator changes to "Away", when they are away from Mattermost.'}),
+                            help_text: defineMessage({id: 'admin.experimental.userStatusAwayTimeout.desc', defaultMessage: 'This setting defines the number of seconds after which the user\'s status indicator changes to "Away", when they are away from Mattermost.'}),
                             help_text_markdown: false,
                             placeholder: defineMessage({id: 'admin.experimental.userStatusAwayTimeout.example', defaultMessage: 'E.g.: "300"'}),
                             isDisabled: it.not(it.userHasWritePermissionOnResource(RESOURCE_KEYS.EXPERIMENTAL.FEATURES)),
diff --git a/webapp/channels/src/components/admin_console/billing/billing_subscriptions/contact_sales_card.tsx b/webapp/channels/src/components/admin_console/billing/billing_subscriptions/contact_sales_card.tsx
index b51f490041..01d5003439 100644
--- a/webapp/channels/src/components/admin_console/billing/billing_subscriptions/contact_sales_card.tsx
+++ b/webapp/channels/src/components/admin_console/billing/billing_subscriptions/contact_sales_card.tsx
@@ -66,7 +66,7 @@ const ContactSalesCard = (props: Props) => {
         description = (
             <FormattedMessage
                 id='admin.billing.subscription.privateCloudCard.cloudEnterprise.description'
-                defaultMessage='At Mattermost, we work with you and your organization to meet your needs throughout the product. If you’re considering a wider rollout, talk to us.'
+                defaultMessage="At Mattermost, we work with you and your organization to meet your needs throughout the product. If you're considering a wider rollout, talk to us."
             />
         );
     } else {
@@ -110,7 +110,7 @@ const ContactSalesCard = (props: Props) => {
             description = (
                 <FormattedMessage
                     id='admin.billing.subscription.privateCloudCard.cloudEnterprise.description'
-                    defaultMessage='At Mattermost, we work with you and your organization to meet your needs throughout the product. If you’re considering a wider rollout, talk to us.'
+                    defaultMessage="At Mattermost, we work with you and your organization to meet your needs throughout the product. If you're considering a wider rollout, talk to us."
                 />
             );
             break;
diff --git a/webapp/channels/src/components/advanced_text_editor/formatting_bar/formatting_bar.test.tsx b/webapp/channels/src/components/advanced_text_editor/formatting_bar/formatting_bar.test.tsx
index 12b991415b..e0c7afc430 100644
--- a/webapp/channels/src/components/advanced_text_editor/formatting_bar/formatting_bar.test.tsx
+++ b/webapp/channels/src/components/advanced_text_editor/formatting_bar/formatting_bar.test.tsx
@@ -81,4 +81,21 @@ describe('FormattingBar', () => {
         expect(screen.queryByLabelText('heading')).toBeVisible();
         expect(onSubmit).not.toHaveBeenCalled();
     });
+
+    test('should disable tooltip when hidden controls are shown', () => {
+        jest.spyOn(Hooks, 'useFormattingBarControls').mockReturnValue({wideMode: 'narrow', ...splitFormattingBarControls('narrow')});
+
+        const {container} = renderWithContext(
+            <FormattingBar {...baseProps}/>,
+        );
+
+        const hiddenControlsButton = screen.getByLabelText('show hidden formatting options');
+
+        // Click to show hidden controls
+        userEvent.click(hiddenControlsButton);
+
+        // Find the WithTooltip component and verify it has disabled prop
+        const tooltipWrapper = container.querySelector('.tooltipContainer');
+        expect(tooltipWrapper).toBeNull(); // Tooltip should not be visible when controls are shown
+    });
 });
diff --git a/webapp/channels/src/components/advanced_text_editor/formatting_bar/formatting_bar.tsx b/webapp/channels/src/components/advanced_text_editor/formatting_bar/formatting_bar.tsx
index 2da334edda..5c2a9b2528 100644
--- a/webapp/channels/src/components/advanced_text_editor/formatting_bar/formatting_bar.tsx
+++ b/webapp/channels/src/components/advanced_text_editor/formatting_bar/formatting_bar.tsx
@@ -10,6 +10,8 @@ import styled from 'styled-components';
 
 import {DotsHorizontalIcon} from '@mattermost/compass-icons/components';
 
+import WithTooltip from 'components/with_tooltip';
+
 import type {ApplyMarkdownOptions} from 'utils/markdown/apply_markdown';
 
 import FormattingIcon, {IconContainer} from './formatting_icon';
@@ -242,20 +244,28 @@ const FormattingBar = (props: FormattingBarProps): JSX.Element => {
 
             {hasHiddenControls && (
                 <>
-                    <IconContainer
-                        id={'HiddenControlsButton' + location}
-                        ref={setReference}
-                        className={classNames({active: showHiddenControls})}
-                        aria-label={HiddenControlsButtonAriaLabel}
-                        type='button'
-                        {...getClickReferenceProps()}
-                        {...getDismissReferenceProps()}
+                    <WithTooltip
+                        title={formatMessage({
+                            id: 'shortcuts.msgs.formatting_bar.more_formatting_options',
+                            defaultMessage: 'More formatting options',
+                        })}
+                        disabled={showHiddenControls}
                     >
-                        <DotsHorizontalIcon
-                            color={'currentColor'}
-                            size={18}
-                        />
-                    </IconContainer>
+                        <IconContainer
+                            id={'HiddenControlsButton' + location}
+                            ref={setReference}
+                            className={classNames({active: showHiddenControls})}
+                            aria-label={HiddenControlsButtonAriaLabel}
+                            type='button'
+                            {...getClickReferenceProps()}
+                            {...getDismissReferenceProps()}
+                        >
+                            <DotsHorizontalIcon
+                                color={'currentColor'}
+                                size={18}
+                            />
+                        </IconContainer>
+                    </WithTooltip>
                 </>
             )}
 
diff --git a/webapp/channels/src/i18n/en.json b/webapp/channels/src/i18n/en.json
index f218f0c700..5eb74b6363 100644
--- a/webapp/channels/src/i18n/en.json
+++ b/webapp/channels/src/i18n/en.json
@@ -5114,6 +5114,7 @@
   "shortcuts.msgs.comp.last_reaction.mac": "React to last message:\t⌘|Shift|⧵",
   "shortcuts.msgs.comp.username": "Username:\t@|[a-z]|Tab",
   "shortcuts.msgs.edit": "Edit last message in channel:\tUp",
+  "shortcuts.msgs.formatting_bar.more_formatting_options": "More formatting options",
   "shortcuts.msgs.formatting_bar.post_priority": "Message priority",
   "shortcuts.msgs.header": "Messages",
   "shortcuts.msgs.input.header": "Works inside an empty input field",