diff --git a/e2e-tests/cypress/tests/integration/channels/plugins/link_tooltip_spec.js b/e2e-tests/cypress/tests/integration/channels/plugins/link_tooltip_spec.js
index 827dc759763..f062af562b2 100644
--- a/e2e-tests/cypress/tests/integration/channels/plugins/link_tooltip_spec.js
+++ b/e2e-tests/cypress/tests/integration/channels/plugins/link_tooltip_spec.js
@@ -17,10 +17,18 @@ describe('Link tooltips', () => {
         cy.shouldNotRunOnCloudEdition();
         cy.shouldHavePluginUploadEnabled();
 
-        // # Set plugin settings
+        // # Set plugin settings, including demo plugin defaults so that
+        // OnConfigurationChange can create the demo user with a valid email
         const newSettings = {
             PluginSettings: {
                 Enable: true,
+                Plugins: {
+                    [demoPlugin.id]: {
+                        channelname: 'demo_plugin',
+                        username: 'demo_plugin',
+                        lastname: 'Plugin User',
+                    },
+                },
             },
             ServiceSettings: {
                 EnableGifPicker: true,
@@ -47,7 +55,7 @@ describe('Link tooltips', () => {
         cy.uiWaitUntilMessagePostedIncludes(url);
 
         // # Hover over the plugin link
-        cy.findByText(url).should('exist').focus();
+        cy.getLastPost().findByText(url).should('exist').focus();
 
         // * Check tooltip has appeared
         cy.findByText('This is a custom tooltip from the Demo Plugin').should('be.visible');
diff --git a/e2e-tests/cypress/tests/support/api/plugin.js b/e2e-tests/cypress/tests/support/api/plugin.js
index 0d9b7e07343..65649b8beaf 100644
--- a/e2e-tests/cypress/tests/support/api/plugin.js
+++ b/e2e-tests/cypress/tests/support/api/plugin.js
@@ -56,14 +56,15 @@ Cypress.Commands.add('apiUploadPlugin', (filename) => {
 
 Cypress.Commands.add('apiUploadAndEnablePlugin', ({filename, url, id, version}) => {
     return cy.apiGetPluginStatus(id, version).then((data) => {
-        // # If already active, then only return the data
-        if (data.isActive) {
+        // # Only short-circuit when version is specified, so we know the exact
+        // installed version matches the desired artifact. Without a version,
+        // any installed version would match and we'd silently skip the install.
+        if (version && data.isActive) {
             cy.log(`${id}: Plugin is active.`);
             return cy.wrap(data);
         }
 
-        // # If already installed, then only enable the plugin
-        if (data.isInstalled) {
+        if (version && data.isInstalled) {
             cy.log(`${id}: Plugin is inactive. Only going to enable.`);
             return cy.apiEnablePluginById(id).then(() => {
                 cy.wait(TIMEOUTS.ONE_SEC);
@@ -71,23 +72,39 @@ Cypress.Commands.add('apiUploadAndEnablePlugin', ({filename, url, id, version})
             });
         }
 
+        // # Remove any old version of the plugin before installing the new one
+        const removeOldVersion = () => {
+            return cy.apiGetPluginStatus(id).then((anyVersionData) => {
+                if (anyVersionData.isInstalled || anyVersionData.isActive) {
+                    cy.log(`${id}: Removing old version before installing new one.`);
+                    return cy.apiRemovePluginById(id);
+                }
+
+                return cy.wrap(null);
+            });
+        };
+
         if (url) {
             // # Upload plugin by URL then enable
             cy.log(`${id}: Plugin is to be uploaded via URL and then enable.`);
-            return cy.apiInstallPluginFromUrl(url).then(() => {
-                cy.wait(TIMEOUTS.FIVE_SEC);
-                return cy.apiEnablePluginById(id).then(() => {
-                    cy.wait(TIMEOUTS.ONE_SEC);
-                    return cy.wrap({isInstalled: true, isActive: true});
+            return removeOldVersion().then(() => {
+                return cy.apiInstallPluginFromUrl(url).then(() => {
+                    cy.wait(TIMEOUTS.FIVE_SEC);
+                    return cy.apiEnablePluginById(id).then(() => {
+                        cy.wait(TIMEOUTS.ONE_SEC);
+                        return cy.wrap({isInstalled: true, isActive: true});
+                    });
                 });
             });
         }
 
         // # Upload plugin by file then enable
         cy.log(`${id}: Plugin is to be uploaded by filename and then enable.`);
-        return cy.apiUploadPlugin(filename).then(() => {
-            return cy.apiEnablePluginById(id).then(() => {
-                return cy.wrap({isInstalled: true, isActive: true});
+        return removeOldVersion().then(() => {
+            return cy.apiUploadPlugin(filename).then(() => {
+                return cy.apiEnablePluginById(id).then(() => {
+                    return cy.wrap({isInstalled: true, isActive: true});
+                });
             });
         });
     });
diff --git a/e2e-tests/cypress/tests/utils/plugins.js b/e2e-tests/cypress/tests/utils/plugins.js
index 30d1d152bff..4ae31cff4ac 100644
--- a/e2e-tests/cypress/tests/utils/plugins.js
+++ b/e2e-tests/cypress/tests/utils/plugins.js
@@ -23,9 +23,9 @@ export const agendaPlugin = {
 
 export const demoPlugin = {
     id: 'com.mattermost.demo-plugin',
-    version: '0.10.0',
-    url: 'https://github.com/mattermost/mattermost-plugin-demo/releases/download/v0.10.0/com.mattermost.demo-plugin-0.10.0.tar.gz',
-    filename: 'com.mattermost.demo-plugin-0.10.0.tar.gz',
+    version: '0.11.0',
+    url: 'https://github.com/mattermost/mattermost-plugin-demo/releases/download/v0.11.0/mattermost-plugin-demo-v0.11.0.tar.gz',
+    filename: 'mattermost-plugin-demo-v0.11.0.tar.gz',
 };
 
 export const demoPluginOld = {
diff --git a/e2e-tests/playwright/specs/functional/plugins/demo_plugin/helpers.ts b/e2e-tests/playwright/specs/functional/plugins/demo_plugin/helpers.ts
index 0b190e58fb6..2aec3e0b5ab 100644
--- a/e2e-tests/playwright/specs/functional/plugins/demo_plugin/helpers.ts
+++ b/e2e-tests/playwright/specs/functional/plugins/demo_plugin/helpers.ts
@@ -7,7 +7,7 @@ import {expect} from '@mattermost/playwright-lib';
 
 const DEMO_PLUGIN_ID = 'com.mattermost.demo-plugin';
 const DEMO_PLUGIN_URL =
-    'https://github.com/mattermost/mattermost-plugin-demo/releases/download/v0.11.0/mattermost-plugin-demo-v0.11.0-linux-amd64.tar.gz';
+    'https://github.com/mattermost/mattermost-plugin-demo/releases/download/v0.11.0/mattermost-plugin-demo-v0.11.0.tar.gz';
 
 export async function setupDemoPlugin(
     adminClient: Client4,
diff --git a/e2e-tests/playwright/specs/functional/plugins/demo_plugin_installation.spec.ts b/e2e-tests/playwright/specs/functional/plugins/demo_plugin_installation.spec.ts
index da848412727..a1cfc72b580 100644
--- a/e2e-tests/playwright/specs/functional/plugins/demo_plugin_installation.spec.ts
+++ b/e2e-tests/playwright/specs/functional/plugins/demo_plugin_installation.spec.ts
@@ -33,7 +33,7 @@ test('should install and enable demo plugin from URL', async ({pw}) => {
     // Install and enable
     await pw.installAndEnablePlugin(
         adminClient,
-        'https://github.com/mattermost/mattermost-plugin-demo/releases/download/v0.11.0/com.mattermost.demo-plugin-0.11.0.tar.gz',
+        'https://github.com/mattermost/mattermost-plugin-demo/releases/download/v0.11.0/mattermost-plugin-demo-v0.11.0.tar.gz',
         'com.mattermost.demo-plugin',
     );
 
diff --git a/webapp/channels/src/components/plugin_link_tooltip/index.test.tsx b/webapp/channels/src/components/plugin_link_tooltip/index.test.tsx
index d1a89b86172..1be98f16331 100644
--- a/webapp/channels/src/components/plugin_link_tooltip/index.test.tsx
+++ b/webapp/channels/src/components/plugin_link_tooltip/index.test.tsx
@@ -94,6 +94,37 @@ describe('PluginLinkTooltip', () => {
         expect(screen.getByTestId('textarea')).toHaveFocus();
     });
 
+    test('should not block interaction with elements outside the tooltip', async () => {
+        renderWithContext(
+            <>
+                <textarea
+                    data-testid='textarea'
+                    defaultValue='some text'
+                />
+                <PluginLinkTooltip
+                    nodeAttributes={{
+                        href: 'https://example.com/tooltip',
+                    }}
+                >
+                    {'This is a link'}
+                </PluginLinkTooltip>
+                <div id={RootHtmlPortalId}/>
+            </>,
+            baseState,
+        );
+
+        // # Hover over the link to show the tooltip
+        await userEvent.hover(screen.getByText('This is a link'));
+        await waitFor(() => {
+            expect(screen.queryByText('This is a link tooltip')).toBeVisible();
+        });
+
+        // * Verify the overlay has pointer-events: none so it doesn't block clicks
+        const overlay = document.querySelector('.plugin-link-tooltip-floating-overlay') as HTMLElement;
+        expect(overlay).toBeInTheDocument();
+        expect(overlay.style.pointerEvents || getComputedStyle(overlay).pointerEvents).toBe('none');
+    });
+
     test('should not take focus when hovered without a tooltip', async () => {
         renderWithContext(
             <>
diff --git a/webapp/channels/src/components/plugin_link_tooltip/plugin_link_tooltip.scss b/webapp/channels/src/components/plugin_link_tooltip/plugin_link_tooltip.scss
index 164584dcc76..fb3e6d74d35 100644
--- a/webapp/channels/src/components/plugin_link_tooltip/plugin_link_tooltip.scss
+++ b/webapp/channels/src/components/plugin_link_tooltip/plugin_link_tooltip.scss
@@ -2,6 +2,11 @@
 
 .plugin-link-tooltip-floating-overlay {
     z-index: variables.$z-index-popover;
+    pointer-events: none;
+
+    > * {
+        pointer-events: auto;
+    }
 }
 
 // This is as per UX guidelines what the container of the
diff --git a/webapp/channels/src/components/post_markdown/index.test.ts b/webapp/channels/src/components/post_markdown/index.test.ts
index 8abdac03cac..cceaad05b56 100644
--- a/webapp/channels/src/components/post_markdown/index.test.ts
+++ b/webapp/channels/src/components/post_markdown/index.test.ts
@@ -5,7 +5,21 @@ import {TestHelper} from 'utils/test_helper';
 
 import type {GlobalState} from 'types/store';
 
-import {makeGetMentionKeysForPost} from './index';
+import {hasPluginTooltips, makeGetMentionKeysForPost} from './index';
+
+describe('hasPluginTooltips', () => {
+    it('should be false when LinkTooltip is an empty array', () => {
+        expect(hasPluginTooltips([])).toBe(false);
+    });
+
+    it('should be false when LinkTooltip is undefined', () => {
+        expect(hasPluginTooltips(undefined)).toBe(false);
+    });
+
+    it('should be true when LinkTooltip has registered components', () => {
+        expect(hasPluginTooltips([{id: 'test', pluginId: 'com.example', component: () => null}])).toBe(true);
+    });
+});
 
 describe('makeGetMentionKeysForPost', () => {
     const channel = TestHelper.getChannelMock({});
diff --git a/webapp/channels/src/components/post_markdown/index.ts b/webapp/channels/src/components/post_markdown/index.ts
index 6172d960bfe..c47f6973ef3 100644
--- a/webapp/channels/src/components/post_markdown/index.ts
+++ b/webapp/channels/src/components/post_markdown/index.ts
@@ -56,6 +56,10 @@ export function makeGetMentionKeysForPost(): (
     );
 }
 
+export function hasPluginTooltips(linkTooltip?: unknown[]): boolean {
+    return Boolean(linkTooltip?.length);
+}
+
 function makeMapStateToProps() {
     const getMentionKeysForPost = makeGetMentionKeysForPost();
 
@@ -73,7 +77,7 @@ function makeMapStateToProps() {
             channel,
             currentTeam,
             pluginHooks: state.plugins.components.MessageWillFormat,
-            hasPluginTooltips: Boolean(state.plugins.components.LinkTooltip),
+            hasPluginTooltips: hasPluginTooltips(state.plugins.components.LinkTooltip),
             isUserCanManageMembers: channel && canManageMembers(state, channel),
             mentionKeys: getMentionKeysForPost(state, ownProps.post, channel),
             highlightKeys: getHighlightWithoutNotificationKeys(state),