diff --git a/frontend/components/DropdownMenu/DropdownMenu.js b/frontend/components/DropdownMenu/DropdownMenu.js
index d97f2dc3..949ca308 100644
--- a/frontend/components/DropdownMenu/DropdownMenu.js
+++ b/frontend/components/DropdownMenu/DropdownMenu.js
@@ -1,5 +1,5 @@
 // @flow
-import React from 'react';
+import React, { Component } from 'react';
 import invariant from 'invariant';
 import { observable } from 'mobx';
 import { observer } from 'mobx-react';
@@ -10,14 +10,14 @@ import { color } from 'styles/constants';
 import { fadeAndScaleIn } from 'styles/animations';
 
 type Props = {
-  label: React.Element<any>,
-  onShow?: () => void,
+  label: React.Element<*>,
+  onOpen?: () => void,
   onClose?: () => void,
-  children?: React.Element<any>,
+  children?: React.Element<*>,
   style?: Object,
 };
 
-@observer class DropdownMenu extends React.Component {
+@observer class DropdownMenu extends Component {
   props: Props;
   actionRef: Object;
   @observable open: boolean = false;
@@ -37,7 +37,7 @@ type Props = {
       this.open = true;
       this.top = targetRect.bottom - bodyRect.top;
       this.right = bodyRect.width - targetRect.left - targetRect.width;
-      if (this.props.onShow) this.props.onShow();
+      if (this.props.onOpen) this.props.onOpen();
     }
   };
 
diff --git a/frontend/components/DropdownMenu/DropdownMenuItem.js b/frontend/components/DropdownMenu/DropdownMenuItem.js
index 3ceb8e10..18d824ce 100644
--- a/frontend/components/DropdownMenu/DropdownMenuItem.js
+++ b/frontend/components/DropdownMenu/DropdownMenuItem.js
@@ -7,7 +7,7 @@ const DropdownMenuItem = ({
   onClick,
   children,
 }: {
-  onClick?: () => void,
+  onClick?: SyntheticEvent => void,
   children?: React.Element<any>,
 }) => {
   return (
@@ -24,11 +24,15 @@ const MenuItem = styled.div`
 
   color: ${color.slateDark};
   display: flex;
-  justify-content: space-between;
+  justify-content: left;
   align-items: center;
   cursor: pointer;
   font-size: 15px;
 
+  svg {
+    margin-right: 8px;
+  }
+
   a {
     text-decoration: none;
     width: 100%;
diff --git a/frontend/components/Editor/Editor.js b/frontend/components/Editor/Editor.js
index 4c41118d..74779c25 100644
--- a/frontend/components/Editor/Editor.js
+++ b/frontend/components/Editor/Editor.js
@@ -8,6 +8,7 @@ import getDataTransferFiles from 'utils/getDataTransferFiles';
 import Flex from 'components/Flex';
 import ClickablePadding from './components/ClickablePadding';
 import Toolbar from './components/Toolbar';
+import BlockInsert from './components/BlockInsert';
 import Placeholder from './components/Placeholder';
 import Markdown from './serializer';
 import createSchema from './schema';
@@ -173,6 +174,8 @@ type KeyData = {
   };
 
   render = () => {
+    const { readOnly, emoji, onSave } = this.props;
+
     return (
       <Flex
         onDrop={this.handleDrop}
@@ -183,24 +186,31 @@ type KeyData = {
         auto
       >
         <MaxWidth column auto>
-          <Header onClick={this.focusAtStart} readOnly={this.props.readOnly} />
-          <Toolbar state={this.state.state} onChange={this.onChange} />
+          <Header onClick={this.focusAtStart} readOnly={readOnly} />
+          {!readOnly &&
+            <Toolbar state={this.state.state} onChange={this.onChange} />}
+          {!readOnly &&
+            <BlockInsert
+              state={this.state.state}
+              onChange={this.onChange}
+              onInsertImage={this.insertImageFile}
+            />}
           <StyledEditor
             innerRef={ref => (this.editor = ref)}
             placeholder="Start with a title…"
             bodyPlaceholder="…the rest is your canvas"
             schema={this.schema}
             plugins={this.plugins}
-            emoji={this.props.emoji}
+            emoji={emoji}
             state={this.state.state}
             onKeyDown={this.onKeyDown}
             onChange={this.onChange}
             onDocumentChange={this.onDocumentChange}
-            onSave={this.props.onSave}
-            readOnly={this.props.readOnly}
+            onSave={onSave}
+            readOnly={readOnly}
           />
           <ClickablePadding
-            onClick={!this.props.readOnly ? this.focusAtEnd : undefined}
+            onClick={!readOnly ? this.focusAtEnd : undefined}
             grow
           />
         </MaxWidth>
diff --git a/frontend/components/Editor/components/BlockInsert.js b/frontend/components/Editor/components/BlockInsert.js
new file mode 100644
index 00000000..fdc7fb60
--- /dev/null
+++ b/frontend/components/Editor/components/BlockInsert.js
@@ -0,0 +1,186 @@
+// @flow
+import React, { Component } from 'react';
+import EditList from '../plugins/EditList';
+import getDataTransferFiles from 'utils/getDataTransferFiles';
+import Portal from 'react-portal';
+import { observable } from 'mobx';
+import { observer } from 'mobx-react';
+import styled from 'styled-components';
+import { color } from 'styles/constants';
+import Icon from 'components/Icon';
+import BlockMenu from 'menus/BlockMenu';
+import type { State } from '../types';
+
+const { transforms } = EditList;
+
+type Props = {
+  state: State,
+  onChange: Function,
+  onInsertImage: File => Promise<*>,
+};
+
+@observer
+export default class BlockInsert extends Component {
+  props: Props;
+  mouseMoveTimeout: number;
+  file: HTMLInputElement;
+
+  @observable active: boolean = false;
+  @observable menuOpen: boolean = false;
+  @observable top: number;
+  @observable left: number;
+  @observable mouseX: number;
+
+  componentDidMount = () => {
+    this.update();
+    window.addEventListener('mousemove', this.handleMouseMove);
+  };
+
+  componentWillUpdate = (nextProps: Props) => {
+    this.update(nextProps);
+  };
+
+  componentWillUnmount = () => {
+    window.removeEventListener('mousemove', this.handleMouseMove);
+  };
+
+  setInactive = () => {
+    if (this.menuOpen) return;
+    this.active = false;
+  };
+
+  handleMouseMove = (ev: SyntheticMouseEvent) => {
+    const windowWidth = window.innerWidth / 3;
+    let active = ev.clientX < windowWidth;
+
+    if (active !== this.active) {
+      this.active = active || this.menuOpen;
+    }
+    if (active) {
+      clearTimeout(this.mouseMoveTimeout);
+      this.mouseMoveTimeout = setTimeout(this.setInactive, 2000);
+    }
+  };
+
+  handleMenuOpen = () => {
+    this.menuOpen = true;
+  };
+
+  handleMenuClose = () => {
+    this.menuOpen = false;
+  };
+
+  update = (props?: Props) => {
+    if (!document.activeElement) return;
+    const { state } = props || this.props;
+    const boxRect = document.activeElement.getBoundingClientRect();
+    const selection = window.getSelection();
+    if (!selection.focusNode) return;
+
+    const range = selection.getRangeAt(0);
+    const rect = range.getBoundingClientRect();
+
+    if (rect.top <= 0 || boxRect.left <= 0) return;
+
+    if (state.startBlock.type === 'heading1') {
+      this.active = false;
+    }
+
+    this.top = Math.round(rect.top + window.scrollY);
+    this.left = Math.round(boxRect.left + window.scrollX - 20);
+  };
+
+  onClickBlock = (
+    ev: SyntheticEvent,
+    type: string | Object,
+    wrapBlock?: string
+  ) => {
+    ev.preventDefault();
+    let { state } = this.props;
+    let transform = state.transform();
+    const { document } = state;
+    const parent = document.getParent(state.startBlock.key);
+
+    // lists get some special treatment
+    if (parent && parent.type === 'list-item') {
+      transform = transforms.unwrapList(
+        transforms
+          .splitListItem(transform.collapseToStart())
+          .collapseToEndOfPreviousBlock()
+      );
+    }
+
+    transform = transform.insertBlock(type);
+
+    if (wrapBlock) transform = transform.wrapBlock(wrapBlock);
+
+    state = transform.focus().apply();
+    this.props.onChange(state);
+    this.active = false;
+  };
+
+  onPickImage = (ev: SyntheticEvent) => {
+    // simulate a click on the file upload input element
+    this.file.click();
+  };
+
+  onChooseImage = async (ev: SyntheticEvent) => {
+    const files = getDataTransferFiles(ev);
+    for (const file of files) {
+      await this.props.onInsertImage(file);
+    }
+  };
+
+  render() {
+    const style = { top: `${this.top}px`, left: `${this.left}px` };
+    const todo = { type: 'list-item', data: { checked: false } };
+
+    return (
+      <Portal isOpened>
+        <Trigger active={this.active} style={style}>
+          <HiddenInput
+            type="file"
+            innerRef={ref => (this.file = ref)}
+            onChange={this.onChooseImage}
+            accept="image/*"
+          />
+          <BlockMenu
+            label={<Icon type="PlusCircle" />}
+            onPickImage={this.onPickImage}
+            onInsertList={ev =>
+              this.onClickBlock(ev, 'list-item', 'bulleted-list')}
+            onInsertTodoList={ev => this.onClickBlock(ev, todo, 'todo-list')}
+            onInsertBreak={ev => this.onClickBlock(ev, 'horizontal-rule')}
+            onOpen={this.handleMenuOpen}
+            onClose={this.handleMenuClose}
+          />
+        </Trigger>
+      </Portal>
+    );
+  }
+}
+
+const HiddenInput = styled.input`
+  position: absolute;
+  top: -100px;
+  left: -100px;
+  visibility: hidden;
+`;
+
+const Trigger = styled.div`
+  position: absolute;
+  z-index: 1;
+  opacity: 0;
+  background-color: ${color.white};
+  border-radius: 4px;
+  transition: opacity 250ms ease-in-out, transform 250ms ease-in-out;
+  line-height: 0;
+  height: 16px;
+  width: 16px;
+  transform: scale(.9);
+
+  ${({ active }) => active && `
+    transform: scale(1);
+    opacity: .9;
+  `}
+`;
diff --git a/frontend/components/Editor/components/Toolbar/components/FormattingToolbar.js b/frontend/components/Editor/components/Toolbar/components/FormattingToolbar.js
index 2b1938bf..c56ef925 100644
--- a/frontend/components/Editor/components/Toolbar/components/FormattingToolbar.js
+++ b/frontend/components/Editor/components/Toolbar/components/FormattingToolbar.js
@@ -9,7 +9,6 @@ import Heading2Icon from 'components/Icon/Heading2Icon';
 import ItalicIcon from 'components/Icon/ItalicIcon';
 import LinkIcon from 'components/Icon/LinkIcon';
 import StrikethroughIcon from 'components/Icon/StrikethroughIcon';
-import BulletedListIcon from 'components/Icon/BulletedListIcon';
 
 export default class FormattingToolbar extends Component {
   props: {
@@ -95,7 +94,6 @@ export default class FormattingToolbar extends Component {
         {this.renderMarkButton('deleted', StrikethroughIcon)}
         {this.renderBlockButton('heading1', Heading1Icon)}
         {this.renderBlockButton('heading2', Heading2Icon)}
-        {this.renderBlockButton('bulleted-list', BulletedListIcon)}
         {this.renderMarkButton('code', CodeIcon)}
         <ToolbarButton onMouseDown={this.onCreateLink}>
           <LinkIcon light />
diff --git a/frontend/components/Editor/plugins.js b/frontend/components/Editor/plugins.js
index c487df2a..30688ea1 100644
--- a/frontend/components/Editor/plugins.js
+++ b/frontend/components/Editor/plugins.js
@@ -1,11 +1,11 @@
 // @flow
 import DropOrPasteImages from '@tommoor/slate-drop-or-paste-images';
 import PasteLinkify from 'slate-paste-linkify';
-import EditList from 'slate-edit-list';
 import CollapseOnEscape from 'slate-collapse-on-escape';
 import TrailingBlock from 'slate-trailing-block';
 import EditCode from 'slate-edit-code';
 import Prism from 'slate-prism';
+import EditList from './plugins/EditList';
 import KeyboardShortcuts from './plugins/KeyboardShortcuts';
 import MarkdownShortcuts from './plugins/MarkdownShortcuts';
 import insertImage from './insertImage';
@@ -35,10 +35,7 @@ const createPlugins = ({ onImageUploadStart, onImageUploadStop }: Options) => {
         );
       },
     }),
-    EditList({
-      types: ['ordered-list', 'bulleted-list', 'todo-list'],
-      typeItem: 'list-item',
-    }),
+    EditList,
     EditCode({
       onlyIn: onlyInCode,
       containerType: 'code',
diff --git a/frontend/components/Editor/plugins/EditList.js b/frontend/components/Editor/plugins/EditList.js
new file mode 100644
index 00000000..7bef46f4
--- /dev/null
+++ b/frontend/components/Editor/plugins/EditList.js
@@ -0,0 +1,7 @@
+// @flow
+import EditList from 'slate-edit-list';
+
+export default EditList({
+  types: ['ordered-list', 'bulleted-list', 'todo-list'],
+  typeItem: 'list-item',
+});
diff --git a/frontend/components/Layout/components/SidebarCollections.js b/frontend/components/Layout/components/SidebarCollections.js
index 8bd83eb5..a1cf5aa2 100644
--- a/frontend/components/Layout/components/SidebarCollections.js
+++ b/frontend/components/Layout/components/SidebarCollections.js
@@ -95,7 +95,7 @@ type Props = {
               <CollectionMenu
                 history={history}
                 collection={collection}
-                onShow={() => (this.menuOpen = true)}
+                onOpen={() => (this.menuOpen = true)}
                 onClose={() => (this.menuOpen = false)}
                 onImport={this.handleImport}
                 open={this.menuOpen}
diff --git a/frontend/menus/BlockMenu.js b/frontend/menus/BlockMenu.js
new file mode 100644
index 00000000..5cd3e611
--- /dev/null
+++ b/frontend/menus/BlockMenu.js
@@ -0,0 +1,49 @@
+// @flow
+import React, { Component } from 'react';
+import Icon from 'components/Icon';
+import { observer } from 'mobx-react';
+import { DropdownMenu, DropdownMenuItem } from 'components/DropdownMenu';
+
+@observer class BlockMenu extends Component {
+  props: {
+    label?: React$Element<*>,
+    onPickImage: SyntheticEvent => void,
+    onInsertList: SyntheticEvent => void,
+    onInsertTodoList: SyntheticEvent => void,
+    onInsertBreak: SyntheticEvent => void,
+  };
+
+  render() {
+    const {
+      label,
+      onPickImage,
+      onInsertList,
+      onInsertTodoList,
+      onInsertBreak,
+      ...rest
+    } = this.props;
+
+    return (
+      <DropdownMenu
+        style={{ marginRight: -70, marginTop: 5 }}
+        label={label}
+        {...rest}
+      >
+        <DropdownMenuItem onClick={onPickImage}>
+          <Icon type="Image" /> Add images
+        </DropdownMenuItem>
+        <DropdownMenuItem onClick={onInsertList}>
+          <Icon type="List" /> Start list
+        </DropdownMenuItem>
+        <DropdownMenuItem onClick={onInsertTodoList}>
+          <Icon type="CheckSquare" /> Start checklist
+        </DropdownMenuItem>
+        <DropdownMenuItem onClick={onInsertBreak}>
+          <Icon type="Minus" /> Add break
+        </DropdownMenuItem>
+      </DropdownMenu>
+    );
+  }
+}
+
+export default BlockMenu;
diff --git a/frontend/menus/CollectionMenu.js b/frontend/menus/CollectionMenu.js
index 6b57bf09..fc29530b 100644
--- a/frontend/menus/CollectionMenu.js
+++ b/frontend/menus/CollectionMenu.js
@@ -12,7 +12,7 @@ import { DropdownMenu, DropdownMenuItem } from 'components/DropdownMenu';
 @observer class CollectionMenu extends Component {
   props: {
     label?: React$Element<any>,
-    onShow?: () => void,
+    onOpen?: () => void,
     onClose?: () => void,
     onImport?: () => void,
     history: Object,
@@ -36,13 +36,13 @@ import { DropdownMenu, DropdownMenuItem } from 'components/DropdownMenu';
   };
 
   render() {
-    const { collection, label, onShow, onClose, onImport } = this.props;
+    const { collection, label, onOpen, onClose, onImport } = this.props;
     const { allowDelete } = collection;
 
     return (
       <DropdownMenu
         label={label || <MoreIcon type="MoreHorizontal" />}
-        onShow={onShow}
+        onOpen={onOpen}
         onClose={onClose}
       >
         {collection &&