diff --git a/apps/desktop/package-lock.json b/apps/desktop/package-lock.json
index 7a7348aba..4974979f6 100644
--- a/apps/desktop/package-lock.json
+++ b/apps/desktop/package-lock.json
@@ -1,12 +1,12 @@
 {
   "name": "@notesnook/desktop",
-  "version": "3.3.5",
+  "version": "3.3.6-beta.0",
   "lockfileVersion": 3,
   "requires": true,
   "packages": {
     "": {
       "name": "@notesnook/desktop",
-      "version": "3.3.5",
+      "version": "3.3.6-beta.0",
       "hasInstallScript": true,
       "license": "GPL-3.0-or-later",
       "dependencies": {
diff --git a/apps/desktop/package.json b/apps/desktop/package.json
index 194205643..f3c1d3163 100644
--- a/apps/desktop/package.json
+++ b/apps/desktop/package.json
@@ -2,7 +2,7 @@
   "name": "@notesnook/desktop",
   "productName": "Notesnook",
   "description": "Your private note taking space",
-  "version": "3.3.5",
+  "version": "3.3.6-beta.0",
   "appAppleId": "1544027013",
   "private": true,
   "main": "./dist/cjs/index.js",
diff --git a/apps/web/package-lock.json b/apps/web/package-lock.json
index 4f90177c9..8ec3c05cb 100644
--- a/apps/web/package-lock.json
+++ b/apps/web/package-lock.json
@@ -1,12 +1,12 @@
 {
   "name": "@notesnook/web",
-  "version": "3.3.5",
+  "version": "3.3.6-beta.0",
   "lockfileVersion": 3,
   "requires": true,
   "packages": {
     "": {
       "name": "@notesnook/web",
-      "version": "3.3.5",
+      "version": "3.3.6-beta.0",
       "hasInstallScript": true,
       "license": "GPL-3.0-or-later",
       "dependencies": {
diff --git a/apps/web/package.json b/apps/web/package.json
index 28a451344..7533b7516 100644
--- a/apps/web/package.json
+++ b/apps/web/package.json
@@ -1,7 +1,7 @@
 {
   "name": "@notesnook/web",
   "description": "Your private note taking space",
-  "version": "3.3.5",
+  "version": "3.3.6-beta.0",
   "private": true,
   "main": "./src/app.js",
   "homepage": "https://notesnook.com/",
diff --git a/apps/web/src/common/drop-handler.ts b/apps/web/src/common/drop-handler.ts
index 89048061f..183c8ab0a 100644
--- a/apps/web/src/common/drop-handler.ts
+++ b/apps/web/src/common/drop-handler.ts
@@ -30,13 +30,18 @@ export async function handleDrop(
   item:
     | ItemReference
     | Context
-    | { type: "trash" | "notebooks" | "favorites" | undefined }
+    | { type: "trash" | "notebooks" | "favorites" | "archive" | undefined }
 ) {
   if (!item.type) return;
 
   const noteIds = getDragData(dataTransfer, "note");
   const notebookIds = getDragData(dataTransfer, "notebook");
-  const { setColor, favorite, delete: trashNotes } = useNoteStore.getState();
+  const {
+    setColor,
+    favorite,
+    delete: trashNotes,
+    archive
+  } = useNoteStore.getState();
   switch (item.type) {
     case "notebook":
       if (noteIds.length > 0) {
@@ -83,5 +88,8 @@ export async function handleDrop(
         await useNoteStore.getState().refresh();
       }
       break;
+    case "archive":
+      archive(true, ...noteIds);
+      break;
   }
 }
diff --git a/apps/web/src/components/editor/tiptap.tsx b/apps/web/src/components/editor/tiptap.tsx
index 3463e4526..5e3e2712f 100644
--- a/apps/web/src/components/editor/tiptap.tsx
+++ b/apps/web/src/components/editor/tiptap.tsx
@@ -118,7 +118,7 @@ function countCharacters(text: string) {
 function countParagraphs(fragment: Fragment) {
   let count = 0;
   fragment.nodesBetween(0, fragment.size, (node) => {
-    if (node.type.name === "paragraph") {
+    if (node.type.name === "paragraph" && node.content.size > 0) {
       count++;
     }
     return true;
@@ -737,7 +737,7 @@ function toIEditor(editor: Editor): IEditor {
 function getSelectedParagraphs(editor: Editor, selection: Selection): number {
   let count = 0;
   editor.state.doc.nodesBetween(selection.from, selection.to, (node) => {
-    if (node.type.name === "paragraph") {
+    if (node.type.name === "paragraph" && node.content.size > 0) {
       count++;
     }
     return true;
diff --git a/apps/web/src/components/navigation-menu/index.tsx b/apps/web/src/components/navigation-menu/index.tsx
index 6f8c67637..5a7476e6e 100644
--- a/apps/web/src/components/navigation-menu/index.tsx
+++ b/apps/web/src/components/navigation-menu/index.tsx
@@ -506,6 +506,8 @@ function RouteItem({
               ? "trash"
               : item.path === "/favorites"
               ? "favorites"
+              : item.path == "/archive"
+              ? "archive"
               : undefined
         });
       }}
diff --git a/apps/web/src/dialogs/feature-dialog.tsx b/apps/web/src/dialogs/feature-dialog.tsx
index 41164fd43..67117c72b 100644
--- a/apps/web/src/dialogs/feature-dialog.tsx
+++ b/apps/web/src/dialogs/feature-dialog.tsx
@@ -91,18 +91,7 @@ const features: Record<FeatureKeys, Feature> = {
             )
           }
         ]
-      : [
-          {
-            title: "Notesnook Circle",
-            subtitle:
-              "Notesnook Circle brings together trusted partners who share our commitment to privacy, transparency, and user freedom. As a member you get exclusive discounts and offers from our partners. Check it out in Settings > Notesnook Circle."
-          },
-          {
-            title: "Collapsible headings",
-            subtitle:
-              "You can now collapse and expand headings in your notes. This makes it easier to manage large notes and focus on specific sections."
-          }
-        ],
+      : [],
     cta: {
       title: strings.gotIt(),
       icon: Checkmark,
diff --git a/packages/core/src/api/user-manager.ts b/packages/core/src/api/user-manager.ts
index 8ab3cc5c4..bd6875833 100644
--- a/packages/core/src/api/user-manager.ts
+++ b/packages/core/src/api/user-manager.ts
@@ -666,6 +666,15 @@ class UserManager {
         usesFallback: await this.usesFallbackPWHash(old_password)
       });
 
+    // retrieve user keys before deriving a new encryption key
+    const oldUserKeys = {
+      attachmentsKey: await this.getAttachmentsKey(),
+      monographPasswordsKey: await this.getMonographPasswordsKey(),
+      inboxKeys: (await this.hasInboxKeys())
+        ? await this.getInboxKeys()
+        : undefined
+    } as const;
+
     await this.db.storage().deriveCryptoKey({
       password: new_password,
       salt
@@ -678,27 +687,33 @@ class UserManager {
     const userEncryptionKey = await this.getEncryptionKey();
     if (userEncryptionKey) {
       const updateUserPayload: Partial<User> = {};
-      const attachmentsKey = await this.getAttachmentsKey();
-      if (attachmentsKey) {
+      if (oldUserKeys.attachmentsKey) {
         user.attachmentsKey = await this.db
           .storage()
-          .encrypt(userEncryptionKey, JSON.stringify(attachmentsKey));
+          .encrypt(
+            userEncryptionKey,
+            JSON.stringify(oldUserKeys.attachmentsKey)
+          );
         updateUserPayload.attachmentsKey = user.attachmentsKey;
       }
-      const monographPasswordsKey = await this.getMonographPasswordsKey();
-      if (monographPasswordsKey) {
+      if (oldUserKeys.monographPasswordsKey) {
         user.monographPasswordsKey = await this.db
           .storage()
-          .encrypt(userEncryptionKey, JSON.stringify(monographPasswordsKey));
+          .encrypt(
+            userEncryptionKey,
+            JSON.stringify(oldUserKeys.monographPasswordsKey)
+          );
         updateUserPayload.monographPasswordsKey = user.monographPasswordsKey;
       }
-      const inboxKeys = await this.getInboxKeys();
-      if (inboxKeys) {
+      if (oldUserKeys.inboxKeys) {
         user.inboxKeys = {
-          public: inboxKeys.publicKey,
+          public: oldUserKeys.inboxKeys.publicKey,
           private: await this.db
             .storage()
-            .encrypt(userEncryptionKey, JSON.stringify(inboxKeys.privateKey))
+            .encrypt(
+              userEncryptionKey,
+              JSON.stringify(oldUserKeys.inboxKeys.privateKey)
+            )
         };
         updateUserPayload.inboxKeys = user.inboxKeys;
       }
diff --git a/packages/editor/src/extensions/heading/__tests__/__snapshots__/heading.test.ts.snap b/packages/editor/src/extensions/heading/__tests__/__snapshots__/heading.test.ts.snap
index 36139c74a..36f948208 100644
--- a/packages/editor/src/extensions/heading/__tests__/__snapshots__/heading.test.ts.snap
+++ b/packages/editor/src/extensions/heading/__tests__/__snapshots__/heading.test.ts.snap
@@ -3,3 +3,13 @@
 exports[`collapse heading > heading collapsed 1`] = `"<h1 data-collapsed="true">Main Heading</h1><p>paragraph.</p><h2>Subheading</h2><p>subheading paragraph</p><h1>Main heading 2</h1><p>paragraph another</p>"`;
 
 exports[`collapse heading > heading uncollapsed 1`] = `"<h1>Main Heading</h1><p>paragraph.</p><h2>Subheading</h2><p>subheading paragraph</p><h1>Main heading 2</h1><p>paragraph another</p>"`;
+
+exports[`replacing collapsed heading with another heading level should not unhide content 1`] = `"<h2 data-collapsed="true">A collapsed heading</h2><p data-hidden="true">Hidden paragraph</p>"`;
+
+exports[`replacing collapsed heading with another node (blockquote) should unhide content 1`] = `"<blockquote><h1 data-collapsed="true">A collpased heading</h1></blockquote><p>Hidden paragraph</p>"`;
+
+exports[`replacing collapsed heading with another node (bulletList) should unhide content 1`] = `"<ul><li><p>A collpased heading</p></li></ul><p>Hidden paragraph</p>"`;
+
+exports[`replacing collapsed heading with another node (codeBlock) should unhide content 1`] = `"<pre><code>A collpased heading</code></pre><p>Hidden paragraph</p>"`;
+
+exports[`replacing collapsed heading with another node (paragraph) should unhide content 1`] = `"<p>A collpased heading</p><p>Hidden paragraph</p>"`;
diff --git a/packages/editor/src/extensions/heading/__tests__/heading.test.ts b/packages/editor/src/extensions/heading/__tests__/heading.test.ts
index 9fda63e91..8f6a8a46d 100644
--- a/packages/editor/src/extensions/heading/__tests__/heading.test.ts
+++ b/packages/editor/src/extensions/heading/__tests__/heading.test.ts
@@ -18,8 +18,9 @@ along with this program.  If not, see <http://www.gnu.org/licenses/>.
 */
 
 import { test, expect } from "vitest";
-import { createEditor } from "../../../../test-utils/index.js";
+import { createEditor, h } from "../../../../test-utils/index.js";
 import { Heading } from "../heading.js";
+import { Editor } from "@tiptap/core";
 
 test("collapse heading", () => {
   const { editor } = createEditor({
@@ -52,3 +53,59 @@ test("collapse heading", () => {
 
   expect(editor.getHTML()).toMatchSnapshot("heading uncollapsed");
 });
+
+test("replacing collapsed heading with another heading level should not unhide content", () => {
+  const el = h("div", [
+    h("h1", ["A collapsed heading"], { "data-collapsed": "true" }),
+    h("p", ["Hidden paragraph"], { "data-hidden": "true" })
+  ]);
+  const { editor } = createEditor({
+    extensions: {
+      heading: Heading.configure({ levels: [1, 2, 3, 4, 5, 6] })
+    },
+    initialContent: el.outerHTML
+  });
+
+  editor.commands.setTextSelection(0);
+  editor.commands.setHeading({ level: 2 });
+
+  expect(editor.getHTML()).toMatchSnapshot();
+});
+
+const nodes: { name: string; setNode: (editor: Editor) => void }[] = [
+  {
+    name: "paragraph",
+    setNode: (editor) => editor.commands.setParagraph()
+  },
+  {
+    name: "codeBlock",
+    setNode: (editor) => editor.commands.setCodeBlock()
+  },
+  {
+    name: "bulletList",
+    setNode: (editor) => editor.commands.toggleList("bulletList", "listItem")
+  },
+  {
+    name: "blockquote",
+    setNode: (editor) => editor.commands.toggleBlockquote()
+  }
+];
+for (const { name, setNode } of nodes) {
+  test(`replacing collapsed heading with another node (${name}) should unhide content`, () => {
+    const el = h("div", [
+      h("h1", ["A collpased heading"], { "data-collapsed": "true" }),
+      h("p", ["Hidden paragraph"], { "data-hidden": "true" })
+    ]);
+    const { editor } = createEditor({
+      extensions: {
+        heading: Heading.configure({ levels: [1, 2, 3, 4, 5, 6] })
+      },
+      initialContent: el.outerHTML
+    });
+
+    editor.commands.setTextSelection(0);
+    setNode(editor);
+
+    expect(editor.getHTML()).toMatchSnapshot();
+  });
+}
diff --git a/packages/editor/src/extensions/heading/heading.ts b/packages/editor/src/extensions/heading/heading.ts
index 465e8d471..45ac83846 100644
--- a/packages/editor/src/extensions/heading/heading.ts
+++ b/packages/editor/src/extensions/heading/heading.ts
@@ -23,10 +23,8 @@ import {
   textblockTypeInputRule
 } from "@tiptap/core";
 import { Heading as TiptapHeading } from "@tiptap/extension-heading";
-import { isClickWithinBounds } from "../../utils/prosemirror.js";
 import { Plugin, PluginKey, Selection, Transaction } from "@tiptap/pm/state";
 import { Node } from "@tiptap/pm/model";
-import { useToolbarStore } from "../../toolbar/stores/toolbar-store.js";
 
 const COLLAPSIBLE_BLOCK_TYPES = [
   "paragraph",
@@ -168,6 +166,14 @@ export const Heading = TiptapHeading.extend({
   addNodeView() {
     return ({ node, getPos, editor, HTMLAttributes }) => {
       const heading = document.createElement(`h${node.attrs.level}`);
+      const contentWrapper = document.createElement("div");
+      const icon = document.createElement("span");
+
+      // providing a minWidth so that empty headings show the blinking cursor
+      contentWrapper.style.minWidth = "1px";
+
+      icon.className = "heading-collapse-icon";
+      icon.contentEditable = "false";
 
       for (const attr in HTMLAttributes) {
         heading.setAttribute(attr, HTMLAttributes[attr]);
@@ -176,50 +182,46 @@ export const Heading = TiptapHeading.extend({
       if (node.attrs.collapsed) heading.dataset.collapsed = "true";
       else delete heading.dataset.collapsed;
 
-      function onClick(e: MouseEvent | TouchEvent) {
-        if (e instanceof MouseEvent && e.button !== 0) return;
-        if (!(e.target instanceof HTMLHeadingElement)) return;
+      function onIconClick(e: MouseEvent | TouchEvent) {
+        e.preventDefault();
+        e.stopPropagation();
+        e.stopImmediatePropagation();
 
         const pos = typeof getPos === "function" ? getPos() : 0;
         if (typeof pos !== "number") return;
 
         const resolvedPos = editor.state.doc.resolve(pos);
-        const calloutAncestor = findParentNodeClosestToPos(
-          resolvedPos,
-          (node) => node.type.name === "callout"
-        );
-        if (calloutAncestor) return;
-
+        const forbiddenParents = ["callout"];
         if (
-          isClickWithinBounds(
-            e,
-            resolvedPos,
-            useToolbarStore.getState().isMobile ? "right" : "left"
+          findParentNodeClosestToPos(resolvedPos, (node) =>
+            forbiddenParents.includes(node.type.name)
           )
         ) {
-          e.preventDefault();
-          e.stopImmediatePropagation();
-
-          editor.commands.command(({ tr }) => {
-            const currentNode = tr.doc.nodeAt(pos);
-            if (currentNode && currentNode.type.name === "heading") {
-              const shouldCollapse = !currentNode.attrs.collapsed;
-              const headingLevel = currentNode.attrs.level;
-
-              tr.setNodeAttribute(pos, "collapsed", shouldCollapse);
-              toggleNodesUnderHeading(tr, pos, headingLevel, shouldCollapse);
-            }
-            return true;
-          });
+          return;
         }
+
+        editor.commands.command(({ tr }) => {
+          const currentNode = tr.doc.nodeAt(pos);
+          if (currentNode && currentNode.type.name === "heading") {
+            const shouldCollapse = !currentNode.attrs.collapsed;
+            const headingLevel = currentNode.attrs.level;
+
+            tr.setNodeAttribute(pos, "collapsed", shouldCollapse);
+            toggleNodesUnderPos(tr, pos, headingLevel, shouldCollapse);
+          }
+          return true;
+        });
       }
 
-      heading.onmousedown = onClick;
-      heading.ontouchstart = onClick;
+      icon.onmousedown = onIconClick;
+      icon.ontouchend = onIconClick;
+
+      heading.appendChild(contentWrapper);
+      heading.appendChild(icon);
 
       return {
         dom: heading,
-        contentDOM: heading,
+        contentDOM: contentWrapper,
         update: (updatedNode) => {
           if (updatedNode.type !== this.type) {
             return false;
@@ -253,17 +255,17 @@ export const Heading = TiptapHeading.extend({
   }
 });
 
-function toggleNodesUnderHeading(
+function toggleNodesUnderPos(
   tr: Transaction,
-  headingPos: number,
+  pos: number,
   headingLevel: number,
   isCollapsing: boolean
 ) {
   const { doc } = tr;
-  const headingNode = doc.nodeAt(headingPos);
-  if (!headingNode || headingNode.type.name !== "heading") return;
+  const node = doc.nodeAt(pos);
+  if (!node) return;
 
-  let nextPos = headingPos + headingNode.nodeSize;
+  let nextPos = pos + node.nodeSize;
   const cursorPos = tr.selection.from;
   let shouldMoveCursor = false;
   let insideCollapsedHeading = false;
@@ -318,8 +320,8 @@ function toggleNodesUnderHeading(
   }
 
   if (shouldMoveCursor) {
-    const headingEndPos = headingPos + headingNode.nodeSize - 1;
-    tr.setSelection(Selection.near(tr.doc.resolve(headingEndPos)));
+    const endPos = pos + node.nodeSize - 1;
+    tr.setSelection(Selection.near(tr.doc.resolve(endPos)));
   }
 }
 
@@ -364,26 +366,27 @@ const headingUpdatePlugin = new Plugin({
     let modified = false;
 
     newDoc.descendants((newNode, pos) => {
-      if (newNode.type.name === "heading") {
-        if (pos >= oldDoc.content.size) return;
+      if (pos >= oldDoc.content.size) return;
 
-        const oldNode = oldDoc.nodeAt(pos);
-        if (
-          oldNode &&
-          oldNode.type.name === "heading" &&
-          oldNode.attrs.level !== newNode.attrs.level
-        ) {
-          /**
-           * if the level of a collapsed heading is changed,
-           * we need to reset visibility of all the nodes under it as there
-           * might be a heading of same or higher level previously
-           * hidden under this heading
-           */
-          if (newNode.attrs.collapsed) {
-            toggleNodesUnderHeading(tr, pos, oldNode.attrs.level, false);
-            toggleNodesUnderHeading(tr, pos, newNode.attrs.level, true);
-            modified = true;
-          }
+      const oldNode = oldDoc.nodeAt(pos);
+      if (
+        oldNode &&
+        oldNode.type.name === "heading" &&
+        oldNode.attrs.level !== newNode.attrs.level
+      ) {
+        /**
+         * if the level of a collapsed heading is changed,
+         * we need to reset visibility of all the nodes under it as there
+         * might be a heading of same or higher level previously
+         * hidden under this heading
+         */
+        if (newNode.type.name === "heading" && newNode.attrs.collapsed) {
+          toggleNodesUnderPos(tr, pos, oldNode.attrs.level, false);
+          toggleNodesUnderPos(tr, pos, newNode.attrs.level, true);
+          modified = true;
+        } else if (newNode.type.name !== "heading" && oldNode.attrs.collapsed) {
+          toggleNodesUnderPos(tr, pos, oldNode.attrs.level, false);
+          modified = true;
         }
       }
     });
diff --git a/packages/editor/styles/styles.css b/packages/editor/styles/styles.css
index 214ce04da..85e398942 100644
--- a/packages/editor/styles/styles.css
+++ b/packages/editor/styles/styles.css
@@ -316,6 +316,31 @@ img.ProseMirror-separator {
 .ProseMirror table p {
   margin: 0;
 }
+
+.ProseMirror td > h1:first-child,
+.ProseMirror td > h2:first-child,
+.ProseMirror td > h3:first-child,
+.ProseMirror td > h4:first-child,
+.ProseMirror td > h5:first-child,
+.ProseMirror td > h6:first-child {
+  margin-top: 0;
+}
+
+.ProseMirror td > ol,
+.ProseMirror td > ul {
+  padding-left: 20px;
+  margin-top: 0;
+}
+
+.ProseMirror td > blockquote {
+  margin-left: 0;
+  margin-top: 0;
+}
+
+.ProseMirror td > blockquote > :first-child  {
+  margin-top: 0;
+}
+
 /* 
 .resize-cursor {
 
@@ -739,6 +764,10 @@ p > *::selection {
   mask-size: cover;
 }
 
+.simple-checklist > li.checked p {
+  opacity: 0.8;
+}
+
 /* Callout */
 .ProseMirror div.callout {
   padding: 15px;
@@ -866,150 +895,133 @@ del.diffdel {
   text-decoration: none;
 }
 
-.ProseMirror h1,
-.ProseMirror h2,
-.ProseMirror h3,
-.ProseMirror h4,
-.ProseMirror h5,
+.ProseMirror h1 ,
+.ProseMirror h2 ,
+.ProseMirror h3 ,
+.ProseMirror h4 ,
+.ProseMirror h5 ,
 .ProseMirror h6 {
-  position: relative;
+  display: flex;
+  align-items: center;
 }
 
-.ProseMirror h1::before,
-.ProseMirror h2::before,
-.ProseMirror h3::before,
-.ProseMirror h4::before,
-.ProseMirror h5::before,
-.ProseMirror h6::before {
-  position: absolute;
+.ProseMirror h1 .heading-collapse-icon,
+.ProseMirror h2 .heading-collapse-icon,
+.ProseMirror h3 .heading-collapse-icon,
+.ProseMirror h4 .heading-collapse-icon,
+.ProseMirror h5 .heading-collapse-icon,
+.ProseMirror h6 .heading-collapse-icon {
   cursor: pointer;
-  content: "";
   background-size: 18px;
-  width: 18px;
-  height: 18px;
+  margin-inline-start: 8px;
 
   background-color: var(--icon);
   mask: url(data:image/svg+xml;base64,PHN2ZyB4bWxucz0iaHR0cDovL3d3dy53My5vcmcvMjAwMC9zdmciIHdpZHRoPSIxZW0iIGhlaWdodD0iMWVtIiB2aWV3Qm94PSIwIDAgMjQgMjQiPjxwYXRoIGZpbGw9IiM4ODg4ODgiIGQ9Ik03LjQxIDguNThMMTIgMTMuMTdsNC41OS00LjU5TDE4IDEwbC02IDZsLTYtNmwxLjQxLTEuNDJaIi8+PC9zdmc+)
     no-repeat 50% 50%;
   mask-size: cover;
-  border: 1px solid var(--background);
 
   transform: rotate(0);
   transition: transform 250ms ease, opacity 200ms ease;
-  left: -22px;
   opacity: 0;
+  user-select: none;
 }
 
-.ProseMirror h1[dir="rtl"]::before,
-.ProseMirror h2[dir="rtl"]::before,
-.ProseMirror h3[dir="rtl"]::before,
-.ProseMirror h4[dir="rtl"]::before,
-.ProseMirror h5[dir="rtl"]::before,
-.ProseMirror h6[dir="rtl"]::before {
-  display: none;
-}
-
-.ProseMirror h1[dir="rtl"]::after,
-.ProseMirror h2[dir="rtl"]::after,
-.ProseMirror h3[dir="rtl"]::after,
-.ProseMirror h4[dir="rtl"]::after,
-.ProseMirror h5[dir="rtl"]::after,
-.ProseMirror h6[dir="rtl"]::after {
-  position: absolute;
-  cursor: pointer;
-  content: "";
-  background-size: 18px;
+.ProseMirror h1 .heading-collapse-icon {
+  margin-top: 3.5px;
   width: 18px;
   height: 18px;
-
-  background-color: var(--icon);
-  mask: url(data:image/svg+xml;base64,PHN2ZyB4bWxucz0iaHR0cDovL3d3dy53My5vcmcvMjAwMC9zdmciIHdpZHRoPSIxZW0iIGhlaWdodD0iMWVtIiB2aWV3Qm94PSIwIDAgMjQgMjQiPjxwYXRoIGZpbGw9IiM4ODg4ODgiIGQ9Ik03LjQxIDguNThMMTIgMTMuMTdsNC41OS00LjU5TDE4IDEwbC02IDZsLTYtNmwxLjQxLTEuNDJaIi8+PC9zdmc+)
-    no-repeat 50% 50%;
-  mask-size: cover;
-  border: 1px solid var(--background);
-
-  transform: rotate(0deg);
-  transition: transform 250ms ease, opacity 200ms ease;
-  right: -22px;
-  opacity: 0;
 }
 
-.ProseMirror h1::before,
-.ProseMirror h1::after {
-  top: 8px;
+.ProseMirror h2 .heading-collapse-icon {
+  margin-top: 3px;
+  width: 16px;
+  height: 16px;
 }
 
-.ProseMirror h2::before,
-.ProseMirror h2::after
- {
-  top: 3px;
+.ProseMirror h3 .heading-collapse-icon {
+  margin-top: 2.3px;
+  width: 15px;
+  height: 15px;
 }
 
-.ProseMirror h3::before,
-.ProseMirror h3::after {
-  top: 0px;
+.ProseMirror h4 .heading-collapse-icon {
+  margin-top: 1.8px;
+  width: 14px;
+  height: 14px;
 }
 
-.ProseMirror h4::before,
-.ProseMirror h4::after {
-  top: -1px; 
+.ProseMirror h5 .heading-collapse-icon {
+  margin-top: 1.3px;
+  width: 13px;
+  height: 13px;
 }
 
-.ProseMirror h5::before,
-.ProseMirror h5::after {
-  top: -2px; 
+.ProseMirror h6 .heading-collapse-icon {
+  margin-top: 0.3px;
+  width: 12px;
+  height: 12px;
 }
 
-.ProseMirror h6::before,
-.ProseMirror h6::after {
-  top: -4px; 
-}
 
-.ProseMirror h1[data-collapsed="true"]::before,
-.ProseMirror h2[data-collapsed="true"]::before,
-.ProseMirror h3[data-collapsed="true"]::before,
-.ProseMirror h4[data-collapsed="true"]::before,
-.ProseMirror h5[data-collapsed="true"]::before,
-.ProseMirror h6[data-collapsed="true"]::before {
+.ProseMirror h1[data-collapsed="true"] .heading-collapse-icon,
+.ProseMirror h2[data-collapsed="true"] .heading-collapse-icon,
+.ProseMirror h3[data-collapsed="true"] .heading-collapse-icon,
+.ProseMirror h4[data-collapsed="true"] .heading-collapse-icon,
+.ProseMirror h5[data-collapsed="true"] .heading-collapse-icon,
+.ProseMirror h6[data-collapsed="true"] .heading-collapse-icon {
   transform: rotate(-90deg);
   opacity: 1;
 }
 
-.ProseMirror h1[data-collapsed="true"]::after,
-.ProseMirror h2[data-collapsed="true"]::after,
-.ProseMirror h3[data-collapsed="true"]::after,
-.ProseMirror h4[data-collapsed="true"]::after,
-.ProseMirror h5[data-collapsed="true"]::after,
-.ProseMirror h6[data-collapsed="true"]::after {
+.ProseMirror h1[data-collapsed="true"][dir="rtl"] .heading-collapse-icon,
+.ProseMirror h2[data-collapsed="true"][dir="rtl"] .heading-collapse-icon,
+.ProseMirror h3[data-collapsed="true"][dir="rtl"] .heading-collapse-icon,
+.ProseMirror h4[data-collapsed="true"][dir="rtl"] .heading-collapse-icon,
+.ProseMirror h5[data-collapsed="true"][dir="rtl"] .heading-collapse-icon,
+.ProseMirror h6[data-collapsed="true"][dir="rtl"] .heading-collapse-icon {
   transform: rotate(90deg);
   opacity: 1;
 }
 
-
-.ProseMirror h1:hover::before,
-.ProseMirror h2:hover::before,
-.ProseMirror h3:hover::before,
-.ProseMirror h4:hover::before,
-.ProseMirror h5:hover::before,
-.ProseMirror h6:hover::before,
-.ProseMirror h1:hover::after,
-.ProseMirror h2:hover::after,
-.ProseMirror h3:hover::after,
-.ProseMirror h4:hover::after,
-.ProseMirror h5:hover::after,
-.ProseMirror h6:hover::after {
+.ProseMirror h1:hover .heading-collapse-icon,
+.ProseMirror h2:hover .heading-collapse-icon,
+.ProseMirror h3:hover .heading-collapse-icon,
+.ProseMirror h4:hover .heading-collapse-icon,
+.ProseMirror h5:hover .heading-collapse-icon,
+.ProseMirror h6:hover .heading-collapse-icon {
   opacity: 1;
 }
 
-.ProseMirror div.callout h1::before,
-.ProseMirror div.callout h2::before,
-.ProseMirror div.callout h3::before,
-.ProseMirror div.callout h4::before,
-.ProseMirror div.callout h5::before,
-.ProseMirror div.callout h6::before {
+.ProseMirror div.callout h1 .heading-collapse-icon,
+.ProseMirror div.callout h2 .heading-collapse-icon,
+.ProseMirror div.callout h3 .heading-collapse-icon,
+.ProseMirror div.callout h4 .heading-collapse-icon,
+.ProseMirror div.callout h5 .heading-collapse-icon,
+.ProseMirror div.callout h6 .heading-collapse-icon {
   display: none;
 }
 
+/* hide collapse icon when heading is empty (only contains trailing break) */
+.ProseMirror h1:has(> div > br.ProseMirror-trailingBreak:only-child) .heading-collapse-icon,
+.ProseMirror h2:has(> div > br.ProseMirror-trailingBreak:only-child) .heading-collapse-icon,
+.ProseMirror h3:has(> div  > br.ProseMirror-trailingBreak:only-child) .heading-collapse-icon,
+.ProseMirror h4:has(> div > br.ProseMirror-trailingBreak:only-child) .heading-collapse-icon,
+.ProseMirror h5:has(> div > br.ProseMirror-trailingBreak:only-child) .heading-collapse-icon,
+.ProseMirror h6:has(> div > br.ProseMirror-trailingBreak:only-child) .heading-collapse-icon {
+  display: none !important;
+}
+
+@media screen and (max-width: 768px) {
+  .ProseMirror h1 .heading-collapse-icon,
+  .ProseMirror h2 .heading-collapse-icon,
+  .ProseMirror h3 .heading-collapse-icon,
+  .ProseMirror h4 .heading-collapse-icon,
+  .ProseMirror h5 .heading-collapse-icon,
+  .ProseMirror h6 .heading-collapse-icon {
+    opacity: 1 !important;
+  }
+}
+
 [data-hidden="true"] {
   display: none !important;
 }
@@ -1028,3 +1040,4 @@ del.diffdel {
 pre[class*="language-"] {
   overflow: initial !important;
 }
+