diff --git a/app/models/Collection.js b/app/models/Collection.js
index 91881f2e2..625bb87ba 100644
--- a/app/models/Collection.js
+++ b/app/models/Collection.js
@@ -11,7 +11,6 @@ import type { NavigationNode } from 'types';
 
 class Collection extends BaseModel {
   isSaving: boolean = false;
-  hasPendingChanges: boolean = false;
   ui: UiStore;
   data: Object;
 
@@ -109,7 +108,6 @@ class Collection extends BaseModel {
       runInAction('Collection#save', () => {
         invariant(res && res.data, 'Data should be available');
         this.updateData(res.data);
-        this.hasPendingChanges = false;
       });
     } catch (e) {
       this.ui.showToast('Collection failed saving');
diff --git a/app/models/Document.js b/app/models/Document.js
index 883effcf2..d45601ccf 100644
--- a/app/models/Document.js
+++ b/app/models/Document.js
@@ -15,7 +15,6 @@ type SaveOptions = { publish?: boolean, done?: boolean, autosave?: boolean };
 
 class Document extends BaseModel {
   isSaving: boolean = false;
-  hasPendingChanges: boolean = false;
   ui: *;
   store: *;
 
@@ -209,7 +208,6 @@ class Document extends BaseModel {
       runInAction('Document#save', () => {
         invariant(res && res.data, 'Data should be available');
         this.updateData(res.data);
-        this.hasPendingChanges = false;
 
         if (isCreating) {
           this.emit('documents.create', this);
@@ -288,13 +286,12 @@ class Document extends BaseModel {
     a.click();
   };
 
-  updateData(data: Object = {}, dirty: boolean = false) {
+  updateData(data: Object = {}) {
     if (data.text) {
       const { title, emoji } = parseTitle(data.text);
       data.title = title;
       data.emoji = emoji;
     }
-    if (dirty) this.hasPendingChanges = true;
     extendObservable(this, data);
   }
 
diff --git a/app/scenes/Document/Document.js b/app/scenes/Document/Document.js
index 839595122..684f03105 100644
--- a/app/scenes/Document/Document.js
+++ b/app/scenes/Document/Document.js
@@ -36,7 +36,8 @@ import Search from 'scenes/Search';
 import Error404 from 'scenes/Error404';
 import ErrorOffline from 'scenes/ErrorOffline';
 
-const AUTOSAVE_INTERVAL = 3000;
+const AUTOSAVE_DELAY = 3000;
+const IS_DIRTY_DELAY = 500;
 const MARK_AS_VIEWED_AFTER = 3000;
 const DISCARD_CHANGES = `
 You have unsaved changes.
@@ -59,16 +60,16 @@ type Props = {
 
 @observer
 class DocumentScene extends React.Component<Props> {
-  savedTimeout: TimeoutID;
   viewTimeout: TimeoutID;
+  getEditorText: () => string;
 
   @observable editorComponent;
-  @observable editCache: ?string;
   @observable document: ?Document;
   @observable newDocument: ?Document;
   @observable isUploading = false;
   @observable isSaving = false;
   @observable isPublishing = false;
+  @observable isDirty = false;
   @observable notFound = false;
   @observable moveModalOpen: boolean = false;
 
@@ -83,14 +84,13 @@ class DocumentScene extends React.Component<Props> {
       this.props.match.params.documentSlug
     ) {
       this.notFound = false;
+      clearTimeout(this.viewTimeout);
       this.loadDocument(nextProps);
     }
   }
 
   componentWillUnmount() {
-    clearTimeout(this.savedTimeout);
     clearTimeout(this.viewTimeout);
-
     this.props.ui.clearActiveDocument();
   }
 
@@ -116,15 +116,13 @@ class DocumentScene extends React.Component<Props> {
         props.match.params.documentSlug,
         { shareId }
       );
+      this.isDirty = false;
 
       const document = this.document;
 
       if (document) {
         this.props.ui.setActiveDocument(document);
 
-        // Cache data if user enters edit mode and cancels
-        this.editCache = document.text;
-
         if (this.props.auth.user && !shareId) {
           if (!this.isEditing && document.publishedAt) {
             this.viewTimeout = setTimeout(document.view, MARK_AS_VIEWED_AFTER);
@@ -163,13 +161,25 @@ class DocumentScene extends React.Component<Props> {
     options: { done?: boolean, publish?: boolean, autosave?: boolean } = {}
   ) => {
     let document = this.document;
-    if (!document || !document.allowSave) return;
+    if (!document) return;
+
+    // get the latest version of the editor text value
+    const text = this.getEditorText ? this.getEditorText() : document.text;
+
+    // prevent autosave if nothing has changed
+    if (options.autosave && document.text.trim() === text.trim()) return;
+
+    document.updateData({ text }, true);
+    if (!document.allowSave) return;
+
+    // prevent autosave before anything has been written
+    if (options.autosave && !document.title && !document.id) return;
 
     let isNew = !document.id;
-    this.editCache = null;
     this.isSaving = true;
     this.isPublishing = !!options.publish;
     document = await document.save(options);
+    this.isDirty = false;
     this.isSaving = false;
     this.isPublishing = false;
 
@@ -182,9 +192,13 @@ class DocumentScene extends React.Component<Props> {
     }
   };
 
-  autosave = debounce(async () => {
+  autosave = debounce(() => {
     this.onSave({ done: false, autosave: true });
-  }, AUTOSAVE_INTERVAL);
+  }, AUTOSAVE_DELAY);
+
+  updateIsDirty = debounce(() => {
+    this.isDirty = this.getEditorText().trim() !== this.document.text.trim();
+  }, IS_DIRTY_DELAY);
 
   onImageUploadStart = () => {
     this.isUploading = true;
@@ -194,14 +208,9 @@ class DocumentScene extends React.Component<Props> {
     this.isUploading = false;
   };
 
-  onChange = text => {
-    let document = this.document;
-    if (!document) return;
-    if (document.text.trim() === text.trim()) return;
-    document.updateData({ text }, true);
-
-    // prevent autosave before anything has been written
-    if (!document.title && !document.id) return;
+  onChange = getEditorText => {
+    this.getEditorText = getEditorText;
+    this.updateIsDirty();
     this.autosave();
   };
 
@@ -209,7 +218,6 @@ class DocumentScene extends React.Component<Props> {
     let url;
     if (this.document && this.document.url) {
       url = this.document.url;
-      if (this.editCache) this.document.updateData({ text: this.editCache });
     } else {
       url = collectionUrl(this.props.match.params.id);
     }
@@ -304,10 +312,7 @@ class DocumentScene extends React.Component<Props> {
           <Container justify="center" column auto>
             {this.isEditing && (
               <React.Fragment>
-                <Prompt
-                  when={document.hasPendingChanges}
-                  message={DISCARD_CHANGES}
-                />
+                <Prompt when={this.isDirty} message={DISCARD_CHANGES} />
                 <Prompt when={this.isUploading} message={UPLOADING_WARNING} />
               </React.Fragment>
             )}
diff --git a/app/scenes/Document/components/Editor.js b/app/scenes/Document/components/Editor.js
index c45fc6040..cb11a2218 100644
--- a/app/scenes/Document/components/Editor.js
+++ b/app/scenes/Document/components/Editor.js
@@ -41,10 +41,20 @@ schema.document.normalize = (
 class Editor extends React.Component<Props> {
   editor: *;
 
+  componentDidMount() {
+    if (!this.props.defaultValue) {
+      this.focusAtStart();
+    }
+  }
+
   setEditorRef = (ref: RichMarkdownEditor) => {
     this.editor = ref;
   };
 
+  focusAtStart = () => {
+    if (this.editor) this.editor.focusAtStart();
+  };
+
   focusAtEnd = () => {
     if (this.editor) this.editor.focusAtEnd();
   };
diff --git a/app/scenes/Document/components/Header.js b/app/scenes/Document/components/Header.js
index 9ac29d043..4ae8202de 100644
--- a/app/scenes/Document/components/Header.js
+++ b/app/scenes/Document/components/Header.js
@@ -161,13 +161,6 @@ class Header extends React.Component<Props> {
               <Link onClick={this.handleEdit}>Edit</Link>
             </Action>
           )}
-          {isEditing &&
-            !isSaving &&
-            document.hasPendingChanges && (
-              <Action>
-                <Link onClick={this.props.onDiscard}>Discard</Link>
-              </Action>
-            )}
           {!isEditing && (
             <Action>
               <DocumentMenu document={document} showPrint />
diff --git a/package.json b/package.json
index 3edd22a41..3d47ccc10 100644
--- a/package.json
+++ b/package.json
@@ -91,7 +91,7 @@
     "copy-to-clipboard": "^3.0.6",
     "css-loader": "^0.28.7",
     "date-fns": "1.29.0",
-    "debug": "2.2.0",
+    "debug": "2.6.9",
     "dotenv": "^4.0.0",
     "emoji-regex": "^6.5.1",
     "exports-loader": "^0.6.4",
@@ -158,7 +158,7 @@
     "react-waypoint": "^7.3.1",
     "redis": "^2.6.2",
     "redis-lock": "^0.1.0",
-    "rich-markdown-editor": "3.1.4",
+    "rich-markdown-editor": "5.0.0",
     "safestart": "1.1.0",
     "sequelize": "4.28.6",
     "sequelize-cli": "^2.7.0",
diff --git a/yarn.lock b/yarn.lock
index c50d32058..580eee2ad 100644
--- a/yarn.lock
+++ b/yarn.lock
@@ -2526,19 +2526,13 @@ debug@*, debug@2.6.8, debug@^2.2.0, debug@^2.3.2, debug@^2.6.1, debug@^2.6.3, de
   dependencies:
     ms "2.0.0"
 
-debug@2.2.0, debug@~2.2.0:
-  version "2.2.0"
-  resolved "https://registry.yarnpkg.com/debug/-/debug-2.2.0.tgz#f87057e995b1a1f6ae6a4960664137bc56f039da"
-  dependencies:
-    ms "0.7.1"
-
 debug@2.6.7:
   version "2.6.7"
   resolved "https://registry.yarnpkg.com/debug/-/debug-2.6.7.tgz#92bad1f6d05bbb6bba22cca88bcd0ec894c2861e"
   dependencies:
     ms "2.0.0"
 
-debug@^2.6.9:
+debug@2.6.9, debug@^2.6.9:
   version "2.6.9"
   resolved "https://registry.yarnpkg.com/debug/-/debug-2.6.9.tgz#5d128515df134ff327e90a4c93f4e077a536341f"
   dependencies:
@@ -2556,6 +2550,12 @@ debug@^3.0.1, debug@^3.1.0:
   dependencies:
     ms "2.0.0"
 
+debug@~2.2.0:
+  version "2.2.0"
+  resolved "https://registry.yarnpkg.com/debug/-/debug-2.2.0.tgz#f87057e995b1a1f6ae6a4960664137bc56f039da"
+  dependencies:
+    ms "0.7.1"
+
 debuglog@^1.0.0:
   version "1.0.1"
   resolved "https://registry.yarnpkg.com/debuglog/-/debuglog-1.0.1.tgz#aa24ffb9ac3df9a2351837cfb2d279360cd78492"
@@ -8858,9 +8858,9 @@ retry-axios@0.3.2, retry-axios@^0.3.2:
   version "0.3.2"
   resolved "https://registry.yarnpkg.com/retry-axios/-/retry-axios-0.3.2.tgz#5757c80f585b4cc4c4986aa2ffd47a60c6d35e13"
 
-rich-markdown-editor@3.1.4:
-  version "3.1.4"
-  resolved "https://registry.yarnpkg.com/rich-markdown-editor/-/rich-markdown-editor-3.1.4.tgz#90e60f599e0ad57b52d893880c89d7ebdfdd97cd"
+rich-markdown-editor@5.0.0:
+  version "5.0.0"
+  resolved "https://registry.yarnpkg.com/rich-markdown-editor/-/rich-markdown-editor-5.0.0.tgz#7c581f5ec3a52f749bc7633ea46b9f3d5b113935"
   dependencies:
     "@tommoor/slate-drop-or-paste-images" "^0.8.1"
     babel-plugin-transform-async-to-generator "^6.24.1"