diff --git a/src/commands/insertAllFiles.ts b/src/commands/insertAllFiles.ts
new file mode 100644
index 000000000..8035b27bd
--- /dev/null
+++ b/src/commands/insertAllFiles.ts
@@ -0,0 +1,125 @@
+import { ToastType } from "../types";
+
+
+// function findPlaceholderLink(doc, href) {
+//   let result;
+
+//   function findLinks(node, pos = 0) {
+//     // get text nodes
+//     if (node.type.name === "text") {
+//       // get marks for text nodes
+//       node.marks.forEach(mark => {
+//         // any of the marks links?
+//         if (mark.type.name === "link") {
+//           // any of the links to other docs?
+//           if (mark.attrs.href === href) {
+//             result = { node, pos };
+//             if (result) return false;
+//           }
+//         }
+//       });
+//     }
+
+//     if (!node.content.size) {
+//       return;
+//     }
+
+//     node.descendants(findLinks);
+//   }
+
+//   findLinks(doc);
+//   return result;
+// }
+
+const insertAllFiles = function(view, event, pos, files, options) {
+  if (files.length === 0) return;
+
+  const {
+    dictionary,
+    uploadFile,
+    onFileUploadStart,
+    onFileUploadStop,
+    onShowToast,
+  } = options;
+
+  if (!uploadFile) {
+    console.warn("uploadFile callback must be defined to handle file uploads.");
+    return;
+  }
+
+  // okay, we have some dropped files and a handler – lets stop this
+  // event going any further up the stack
+  event.preventDefault();
+
+  // let the user know we're starting to process the files
+  if (onFileUploadStart) onFileUploadStart();
+
+  // we'll use this to track of how many files have succeeded or failed
+  let complete = 0;
+
+  const { state } = view;
+  const { from, to } = state.selection;
+
+  console.log("state.selection: " + state.selection + "," + from + "," + to);
+
+  // the user might have dropped multiple files at once, we need to loop
+    for (const file of files) {
+
+    // Insert a placeholder link
+    var placeholder = `[${file.name} uploading...]`
+    // const phref = `#uploading_${file.name}`;
+    view.dispatch(
+      view.state.tr
+        .insertText(placeholder, from, to-1)
+    );
+    // start uploading the file file to the server. Using "then" syntax
+    // to allow all placeholders to be entered at once with the uploads
+    // happening in the background in parallel.
+    uploadFile(file)
+      .then(src => {
+        const title = file.name;
+        const href = src;
+
+        // const result = findPlaceholderLink(view.state.doc, phref);
+        // console.log("placeholder: " + result + "," + result.pos + "," + result.node.nodeSize);
+        // if (result) {
+          // view.dispatch(
+          //   view.state.tr
+          //     .removeMark(
+          //       result.pos,
+          //       result.pos + result.node.nodeSize,
+          //       state.schema.marks.link
+          //     )
+          // );
+        // }
+
+        view.dispatch(
+          view.state.tr
+            .delete(from, to + placeholder.length)
+            .insertText(title, from, to)
+            .addMark(
+              from,
+              to + title.length,
+              state.schema.marks.link.create({ href })
+            )
+        );
+      })
+      .catch(error => {
+        console.error(error);
+        if (onShowToast) {
+          onShowToast(dictionary.fileUploadError, ToastType.Error);
+        }
+      })
+      // eslint-disable-next-line no-loop-func
+      .finally(() => {
+        complete++;
+        
+        // once everything is done, let the user know
+        if (complete === files.length) {
+          if (onFileUploadStop) onFileUploadStop();
+        }
+      });
+  }
+};
+
+export default insertAllFiles;
diff --git a/src/components/CommandMenu.tsx b/src/components/CommandMenu.tsx
index 9b5227633..9a0f285f8 100644
--- a/src/components/CommandMenu.tsx
+++ b/src/components/CommandMenu.tsx
@@ -10,6 +10,7 @@ import VisuallyHidden from "./VisuallyHidden";
 import getDataTransferFiles from "../lib/getDataTransferFiles";
 import filterExcessSeparators from "../lib/filterExcessSeparators";
 import insertFiles from "../commands/insertFiles";
+import insertAllFiles from "../commands/insertAllFiles";
 import baseDictionary from "../dictionary";
 
 const SSR = typeof window === "undefined";
@@ -29,8 +30,11 @@ export type Props<T extends MenuItem = MenuItem> = {
   view: EditorView;
   search: string;
   uploadImage?: (file: File) => Promise<string>;
+  uploadFile?: (file: File) => Promise<string>;
   onImageUploadStart?: () => void;
   onImageUploadStop?: () => void;
+  onFileUploadStart?: () => void;
+  onFileUploadStop?: () => void;
   onShowToast?: (message: string, id: string) => void;
   onLinkToolbarOpen?: () => void;
   onClose: () => void;
@@ -61,6 +65,7 @@ type State = {
 class CommandMenu<T = MenuItem> extends React.Component<Props<T>, State> {
   menuRef = React.createRef<HTMLDivElement>();
   inputRef = React.createRef<HTMLInputElement>();
+  fileInputRef = React.createRef<HTMLInputElement>();
 
   state: State = {
     left: -1000,
@@ -177,6 +182,8 @@ class CommandMenu<T = MenuItem> extends React.Component<Props<T>, State> {
     switch (item.name) {
       case "image":
         return this.triggerImagePick();
+      case "file":
+        return this.triggerFilePick();
       case "embed":
         return this.triggerLinkInput(item);
       case "link": {
@@ -254,6 +261,12 @@ class CommandMenu<T = MenuItem> extends React.Component<Props<T>, State> {
     }
   };
 
+  triggerFilePick = () => {
+    if (this.fileInputRef.current) {
+      this.fileInputRef.current.click();
+    }
+  };
+
   triggerLinkInput = item => {
     this.setState({ insertItem: item });
   };
@@ -294,6 +307,38 @@ class CommandMenu<T = MenuItem> extends React.Component<Props<T>, State> {
     this.props.onClose();
   };
 
+  handleFilePicked = event => {
+    const files = getDataTransferFiles(event);
+
+    const {
+      view,
+      uploadFile,
+      onFileUploadStart,
+      onFileUploadStop,
+      onShowToast,
+    } = this.props;
+    const { state } = view;
+    const parent = findParentNode(node => !!node)(state.selection);
+
+    this.clearSearch();
+
+    if (parent) {
+      insertAllFiles(view, event, parent.pos, files, {
+        uploadFile,
+        onFileUploadStart,
+        onFileUploadStop,
+        onShowToast,
+        dictionary: this.props.dictionary,
+      });
+    }
+
+    if (this.inputRef.current) {
+      this.inputRef.current.value = "";
+    }
+
+    this.props.onClose();
+  };
+
   clearSearch = () => {
     this.props.onClearSearch();
   };
@@ -400,6 +445,7 @@ class CommandMenu<T = MenuItem> extends React.Component<Props<T>, State> {
       embeds = [],
       search = "",
       uploadImage,
+      uploadFile,
       commands,
       filterable = true,
     } = this.props;
@@ -425,6 +471,9 @@ class CommandMenu<T = MenuItem> extends React.Component<Props<T>, State> {
     const filtered = items.filter(item => {
       if (item.name === "separator") return true;
 
+      // If file upload callback has been passed, filter the file block in
+      if (uploadFile && item.name === "file") return true;
+
       // Some extensions may be disabled, remove corresponding menu items
       if (
         item.name &&
@@ -454,7 +503,7 @@ class CommandMenu<T = MenuItem> extends React.Component<Props<T>, State> {
   }
 
   render() {
-    const { dictionary, isActive, uploadImage } = this.props;
+    const { dictionary, isActive, uploadImage, uploadFile } = this.props;
     const items = this.filtered;
     const { insertItem, ...positioning } = this.state;
 
@@ -522,6 +571,16 @@ class CommandMenu<T = MenuItem> extends React.Component<Props<T>, State> {
               />
             </VisuallyHidden>
           )}
+          {uploadFile && (
+            <VisuallyHidden>
+              <input
+                type="file"
+                ref={this.fileInputRef}
+                onChange={this.handleFilePicked}
+                accept="*"
+              />
+            </VisuallyHidden>
+          )}
         </Wrapper>
       </Portal>
     );
diff --git a/src/dictionary.ts b/src/dictionary.ts
index 809729805..9e0ebb726 100644
--- a/src/dictionary.ts
+++ b/src/dictionary.ts
@@ -25,6 +25,7 @@ export const base = {
   alignImageDefault: "Center large",
   em: "Italic",
   embedInvalidLink: "Sorry, that link won’t work for this embed type",
+  file: "File",
   findOrCreateDoc: "Find or create a doc…",
   h1: "Big heading",
   h2: "Medium heading",
diff --git a/src/index.tsx b/src/index.tsx
index 29eed9fba..e678f7789 100644
--- a/src/index.tsx
+++ b/src/index.tsx
@@ -110,6 +110,7 @@ export type Props = {
     | "heading"
     | "hr"
     | "image"
+    | "file"
     | "list_item"
     | "container_notice"
     | "ordered_list"
@@ -135,6 +136,7 @@ export type Props = {
     [name: string]: (view: EditorView, event: Event) => boolean;
   };
   uploadImage?: (file: File) => Promise<string>;
+  uploadFile?: (file: File) => Promise<string>;
   onBlur?: () => void;
   onFocus?: () => void;
   onSave?: ({ done: boolean }) => void;
@@ -142,6 +144,8 @@ export type Props = {
   onChange?: (value: () => string) => void;
   onImageUploadStart?: () => void;
   onImageUploadStop?: () => void;
+  onFileUploadStart?: () => void;
+  onFileUploadStop?: () => void;
   onCreateLink?: (title: string) => Promise<string>;
   onSearchLink?: (term: string) => Promise<SearchResult[]>;
   onClickLink: (href: string, event: MouseEvent) => void;
@@ -180,6 +184,12 @@ class RichMarkdownEditor extends React.PureComponent<Props, State> {
     onImageUploadStop: () => {
       // no default behavior
     },
+    onFileUploadStart: () => {
+      // no default behavior
+    },
+    onFileUploadStop: () => {
+      // no default behavior
+    },
     onClickLink: href => {
       window.open(href, "_blank");
     },
@@ -805,9 +815,12 @@ class RichMarkdownEditor extends React.PureComponent<Props, State> {
                   search={this.state.blockMenuSearch}
                   onClose={this.handleCloseBlockMenu}
                   uploadImage={this.props.uploadImage}
+                  uploadFile={this.props.uploadFile}
                   onLinkToolbarOpen={this.handleOpenLinkMenu}
                   onImageUploadStart={this.props.onImageUploadStart}
                   onImageUploadStop={this.props.onImageUploadStop}
+                  onFileUploadStart={this.props.onFileUploadStart}
+                  onFileUploadStop={this.props.onFileUploadStop}
                   onShowToast={this.props.onShowToast}
                   embeds={this.props.embeds}
                 />
diff --git a/src/menus/block.ts b/src/menus/block.ts
index 59d355c96..0d4c5821a 100644
--- a/src/menus/block.ts
+++ b/src/menus/block.ts
@@ -11,6 +11,7 @@ import {
   TableIcon,
   TodoListIcon,
   ImageIcon,
+  NotepadIcon,
   StarredIcon,
   WarningIcon,
   InfoIcon,
@@ -115,6 +116,12 @@ export default function blockMenuItems(
       icon: ImageIcon,
       keywords: "picture photo",
     },
+    {
+      name: "file",
+      title: dictionary.file,
+      icon: NotepadIcon,
+      keywords: "doc pdf",
+    },
     {
       name: "link",
       title: dictionary.link,
diff --git a/tsconfig.json b/tsconfig.json
index 950397d17..3a4f70612 100644
--- a/tsconfig.json
+++ b/tsconfig.json
@@ -29,4 +29,4 @@
     "dist",
     "node_modules"
   ]
-}
\ No newline at end of file
+}