diff --git a/src/content_scripts/main.js b/src/content_scripts/main.js
index 8f5ed5653d..750f137514 100644
--- a/src/content_scripts/main.js
+++ b/src/content_scripts/main.js
@@ -107,6 +107,26 @@
     document.documentElement.append(script);
   });
 
+  /**
+   * Shows an informative modal if the extension context is invalidated (e.g. after extension is autoupdated
+   * or manually disabled in Chromium). Should do nothing in Firefox, which stops running all extension
+   * context javascript immediately.
+   */
+  const warnOnExtensionContextInvalidated = async () => {
+    const { showContextInvalidatedModal } = await import(browser.runtime.getURL('/utils/modals.js'));
+
+    const isExtensionContextValid = () => { try { browser.runtime.getURL(''); return true; } catch { return false; } };
+
+    let failures = 0;
+    const intervalID = setInterval(() => {
+      failures = isExtensionContextValid() ? 0 : failures + 1;
+      if (failures >= 5 && !document.getElementById('xkit-modal')) {
+        showContextInvalidatedModal();
+        clearInterval(intervalID);
+      }
+    }, 1000);
+  };
+
   const init = async function () {
     $('style.xkit, link.xkit').remove();
 
@@ -130,6 +150,8 @@
     installedFeatures
       .filter(featureName => enabledFeatures.includes(featureName))
       .forEach(runFeature);
+
+    warnOnExtensionContextInvalidated();
   };
 
   const waitForReactLoaded = async function () {
diff --git a/src/features/mass_deleter/index.js b/src/features/mass_deleter/index.js
index 8f2b476f05..5873c6eee6 100644
--- a/src/features/mass_deleter/index.js
+++ b/src/features/mass_deleter/index.js
@@ -1,6 +1,6 @@
 import { button, form, input, label, small, span } from '../../utils/dom.js';
 import { megaEdit } from '../../utils/mega_editor.js';
-import { createBlogSpan, modalCancelButton, modalCompleteButton, showErrorModal, showModal } from '../../utils/modals.js';
+import { createBlogSpan, hideModal, modalCancelButton, modalCompleteButton, showErrorModal, showModal } from '../../utils/modals.js';
 import { addSidebarItem, removeSidebarItem } from '../../utils/sidebar.js';
 import { dateTimeFormat } from '../../utils/text_format.js';
 import { apiFetch } from '../../utils/tumblr_helpers.js';
@@ -131,7 +131,8 @@ const deleteDrafts = async function ({ blogName, before }) {
       'Refresh the page to see the result.',
     ],
     buttons: [
-      button({ class: 'blue', click: () => location.reload() }, ['Refresh']),
+      button({ click: hideModal }, ['Close']),
+      button({ class: 'blue', click: () => location.reload() }, ['Refresh Now']),
     ],
   });
 };
@@ -225,7 +226,8 @@ const clearQueue = async function ({ blogName }) {
       'Refresh the page to see the result.',
     ],
     buttons: [
-      button({ class: 'blue', click: () => location.reload() }, ['Refresh']),
+      button({ click: hideModal }, ['Close']),
+      button({ class: 'blue', click: () => location.reload() }, ['Refresh Now']),
     ],
   });
 };
diff --git a/src/features/mass_privater/index.js b/src/features/mass_privater/index.js
index 671e65c6fb..2980bb5716 100644
--- a/src/features/mass_privater/index.js
+++ b/src/features/mass_privater/index.js
@@ -236,7 +236,7 @@ const privatePosts = async ({ uuid, name, tags, before }) => {
     ],
     buttons: [
       dom('button', null, { click: hideModal }, ['Close']),
-      dom('button', { class: 'blue' }, { click: () => location.reload() }, ['Refresh']),
+      dom('button', { class: 'blue' }, { click: () => location.reload() }, ['Refresh Now']),
     ],
   });
 };
diff --git a/src/utils/modals.js b/src/utils/modals.js
index 6c5ffdc846..e8a853fc52 100644
--- a/src/utils/modals.js
+++ b/src/utils/modals.js
@@ -72,5 +72,19 @@ export const withModalOnError = func =>
     }
   };
 
+export const showContextInvalidatedModal = () =>
+  showModal({
+    title: 'XKit Rewritten has become unloaded.',
+    message: [
+      'If this is unexpected, this is likely due to your browser automatically applying an XKit version update.',
+      '\n\n',
+      'Outdated XKit modifications will be updated/removed after you refresh this Tumblr tab.',
+    ],
+    buttons: [
+      dom('button', null, { click: hideModal }, ['Close']),
+      dom('button', { class: 'blue' }, { click: () => location.reload() }, ['Refresh Now']),
+    ],
+  });
+
 export const createTagSpan = tag => dom('span', { class: 'xkit-modal-tag' }, null, [tag]);
 export const createBlogSpan = name => dom('span', { class: 'xkit-modal-blog' }, null, [name]);