diff --git a/x-pack/plugins/canvas/canvas_plugin_src/uis/arguments/image_upload/forms/file.js b/x-pack/plugins/canvas/canvas_plugin_src/uis/arguments/image_upload/forms/file.js
index af8dc1cf37d13b..c51c949568dc2d 100644
--- a/x-pack/plugins/canvas/canvas_plugin_src/uis/arguments/image_upload/forms/file.js
+++ b/x-pack/plugins/canvas/canvas_plugin_src/uis/arguments/image_upload/forms/file.js
@@ -5,11 +5,21 @@
  */
 import React from 'react';
 import PropTypes from 'prop-types';
+import { EuiFilePicker } from '@elastic/eui';
 import { Loading } from '../../../../../public/components/loading/loading';
-import { FileUpload } from '../../../../../public/components/file_upload';
 
-export const FileForm = ({ loading, onUpload }) =>
-  loading ? <Loading animated text="Image uploading" /> : <FileUpload onUpload={onUpload} />;
+export const FileForm = ({ loading, onChange }) =>
+  loading ? (
+    <Loading animated text="Image uploading" />
+  ) : (
+    <EuiFilePicker
+      initialPromptText="Select or drag and drop an image"
+      onChange={onChange}
+      compressed
+      className="canvasImageUpload"
+      accept="image/*"
+    />
+  );
 
 FileForm.propTypes = {
   loading: PropTypes.bool,
diff --git a/x-pack/plugins/canvas/canvas_plugin_src/uis/arguments/image_upload/index.js b/x-pack/plugins/canvas/canvas_plugin_src/uis/arguments/image_upload/index.js
index d40182a1121cd3..e667169b998158 100644
--- a/x-pack/plugins/canvas/canvas_plugin_src/uis/arguments/image_upload/index.js
+++ b/x-pack/plugins/canvas/canvas_plugin_src/uis/arguments/image_upload/index.js
@@ -7,6 +7,7 @@
 import React from 'react';
 import PropTypes from 'prop-types';
 import { EuiSpacer, EuiButtonGroup } from '@elastic/eui';
+import { get } from 'lodash';
 import { AssetPicker } from '../../../../public/components/asset_picker';
 import { elasticOutline } from '../../../lib/elastic_outline';
 import { resolveFromArgs } from '../../../../common/lib/resolve_dataurl';
@@ -14,6 +15,7 @@ import { isValidHttpUrl } from '../../../../common/lib/httpurl';
 import { encode } from '../../../../common/lib/dataurl';
 import { templateFromReactComponent } from '../../../../public/lib/template_from_react_component';
 import './image_upload.scss';
+import { VALID_IMAGE_TYPES } from '../../../../common/lib/constants';
 import { FileForm, LinkForm } from './forms';
 
 class ImageUpload extends React.Component {
@@ -71,17 +73,21 @@ class ImageUpload extends React.Component {
 
   handleUpload = files => {
     const { onAssetAdd } = this.props;
-    const [upload] = files;
-    this.setState({ loading: true }); // start loading indicator
+    const [file] = files;
 
-    encode(upload)
-      .then(dataurl => onAssetAdd('dataurl', dataurl))
-      .then(assetId => {
-        this.updateAST(assetId);
+    const [type, subtype] = get(file, 'type', '').split('/');
+    if (type === 'image' && VALID_IMAGE_TYPES.indexOf(subtype) >= 0) {
+      this.setState({ loading: true }); // start loading indicator
 
-        // this component can go away when onValueChange is called, check for _isMounted
-        this._isMounted && this.setState({ loading: false }); // set loading state back to false
-      });
+      encode(file)
+        .then(dataurl => onAssetAdd('dataurl', dataurl))
+        .then(assetId => {
+          this.updateAST(assetId);
+
+          // this component can go away when onValueChange is called, check for _isMounted
+          this._isMounted && this.setState({ loading: false }); // set loading state back to false
+        });
+    }
   };
 
   changeUrlType = optionId => {
@@ -119,7 +125,7 @@ class ImageUpload extends React.Component {
     );
 
     const forms = {
-      file: <FileForm loading={loading} onUpload={this.handleUpload} />,
+      file: <FileForm loading={loading} onChange={this.handleUpload} />,
       link: (
         <LinkForm
           url={url}
diff --git a/x-pack/plugins/canvas/common/lib/constants.js b/x-pack/plugins/canvas/common/lib/constants.js
index 89eb54ee8ef6e6..774f50e636e6c4 100644
--- a/x-pack/plugins/canvas/common/lib/constants.js
+++ b/x-pack/plugins/canvas/common/lib/constants.js
@@ -18,3 +18,4 @@ export const FETCH_TIMEOUT = 30000; // 30 seconds
 export const CANVAS_USAGE_TYPE = 'canvas';
 export const SECURITY_AUTH_MESSAGE = 'Authentication failed';
 export const DEFAULT_WORKPAD_CSS = '.canvasPage {\n\n}';
+export const VALID_IMAGE_TYPES = ['gif', 'jpeg', 'png', 'svg+xml'];
diff --git a/x-pack/plugins/canvas/public/components/asset_manager/asset_manager.js b/x-pack/plugins/canvas/public/components/asset_manager/asset_manager.js
index 685eee91e282a3..f10691b0ca021b 100644
--- a/x-pack/plugins/canvas/public/components/asset_manager/asset_manager.js
+++ b/x-pack/plugins/canvas/public/components/asset_manager/asset_manager.js
@@ -26,24 +26,31 @@ import {
   EuiSpacer,
   EuiTextColor,
   EuiToolTip,
+  EuiFilePicker,
+  EuiEmptyPrompt,
 } from '@elastic/eui';
 import { ConfirmModal } from '../confirm_modal';
 import { Clipboard } from '../clipboard';
 import { Download } from '../download';
+import { Loading } from '../loading';
 
 export class AssetManager extends React.PureComponent {
   static propTypes = {
     assets: PropTypes.array,
     addImageElement: PropTypes.func,
-    removeAsset: PropTypes.func,
-    copyAsset: PropTypes.func,
+    removeAsset: PropTypes.func.isRequired,
+    copyAsset: PropTypes.func.isRequired,
+    onAssetAdd: PropTypes.func.isRequired,
   };
 
   state = {
     deleteId: null,
     isModalVisible: false,
+    loading: false,
   };
 
+  _isMounted = true;
+
   showModal = () => this.setState({ isModalVisible: true });
   closeModal = () => this.setState({ isModalVisible: false });
 
@@ -52,6 +59,13 @@ export class AssetManager extends React.PureComponent {
     this.props.removeAsset(this.state.deleteId);
   };
 
+  handleFileUpload = files => {
+    this.setState({ loading: true });
+    Promise.all(Array.from(files).map(file => this.props.onAssetAdd(file))).finally(() => {
+      this._isMounted && this.setState({ loading: false });
+    });
+  };
+
   addElement = assetId => {
     this.props.addImageElement(assetId);
   };
@@ -132,16 +146,32 @@ export class AssetManager extends React.PureComponent {
   );
 
   render() {
-    const { isModalVisible } = this.state;
+    const { isModalVisible, loading } = this.state;
+    const { assets } = this.props;
 
     const assetMaxLimit = 25000;
 
     const assetsTotal = Math.round(
-      this.props.assets.reduce((total, asset) => total + asset.value.length, 0) / 1024
+      assets.reduce((total, asset) => total + asset.value.length, 0) / 1024
     );
 
     const percentageUsed = Math.round((assetsTotal / assetMaxLimit) * 100);
 
+    const emptyAssets = (
+      <EuiPanel className="canvasAssetManager__emptyPanel">
+        <EuiEmptyPrompt
+          iconType="importAction"
+          title={<h2>No available assets</h2>}
+          titleSize="s"
+          body={
+            <Fragment>
+              <p>Upload your assets above to get started</p>
+            </Fragment>
+          }
+        />
+      </EuiPanel>
+    );
+
     const assetModal = isModalVisible ? (
       <EuiOverlayMask>
         <EuiModal
@@ -153,6 +183,40 @@ export class AssetManager extends React.PureComponent {
             <EuiModalHeaderTitle className="canvasAssetManager__modalHeaderTitle">
               Manage workpad assets
             </EuiModalHeaderTitle>
+            <EuiFlexGroup className="canvasAssetManager__fileUploadWrapper">
+              <EuiFlexItem grow={false}>
+                {loading ? (
+                  <Loading animated text="Uploading images" />
+                ) : (
+                  <EuiFilePicker
+                    initialPromptText="Select or drag and drop images"
+                    compressed
+                    multiple
+                    onChange={this.handleFileUpload}
+                    accept="image/*"
+                  />
+                )}
+              </EuiFlexItem>
+            </EuiFlexGroup>
+          </EuiModalHeader>
+          <EuiModalBody>
+            <EuiText size="s" color="subdued">
+              <p>
+                Below are the image assets that you added to this workpad. To reclaim space, delete
+                assets that you no longer need. Unfortunately, any assets that are actually in use
+                cannot be determined at this time.
+              </p>
+            </EuiText>
+            <EuiSpacer />
+            {assets.length ? (
+              <EuiFlexGrid responsive={false} columns={4}>
+                {assets.map(this.renderAsset)}
+              </EuiFlexGrid>
+            ) : (
+              emptyAssets
+            )}
+          </EuiModalBody>
+          <EuiModalFooter className="canvasAssetManager__modalFooter">
             <EuiFlexGroup className="canvasAssetManager__meterWrapper" responsive={false}>
               <EuiFlexItem>
                 <EuiProgress
@@ -167,20 +231,6 @@ export class AssetManager extends React.PureComponent {
                 <EuiText id="CanvasAssetManagerLabel">{percentageUsed}% space used</EuiText>
               </EuiFlexItem>
             </EuiFlexGroup>
-          </EuiModalHeader>
-          <EuiModalBody>
-            <EuiText size="s" color="subdued">
-              <p>
-                Below are the image assets that you added to this workpad. To reclaim space, delete
-                assets that you no longer need. Unfortunately, any assets that are actually in use
-                cannot be determined at this time.
-              </p>
-            </EuiText>
-            <EuiFlexGrid responsive={false} columns={4}>
-              {this.props.assets.map(this.renderAsset)}
-            </EuiFlexGrid>
-          </EuiModalBody>
-          <EuiModalFooter>
             <EuiButton size="s" onClick={this.closeModal}>
               Close
             </EuiButton>
diff --git a/x-pack/plugins/canvas/public/components/asset_manager/asset_manager.scss b/x-pack/plugins/canvas/public/components/asset_manager/asset_manager.scss
index 80ab585c963c23..84534971d0ec57 100644
--- a/x-pack/plugins/canvas/public/components/asset_manager/asset_manager.scss
+++ b/x-pack/plugins/canvas/public/components/asset_manager/asset_manager.scss
@@ -1,5 +1,4 @@
 .canvasAssetManager {
-
   .canvasAssetManager__modalHeader {
     flex-wrap: wrap;
   }
@@ -15,8 +14,6 @@
     flex-grow: 0;
     min-width: 40%;
     align-items: center;
-    justify-content: flex-end;
-    padding-right: $euiSize;
 
     @include euiBreakpoint('xs', 's') {
       flex-grow: 1;
@@ -27,6 +24,11 @@
     margin: 0;
   }
 
+  .canvasAssetManager__fileUploadWrapper {
+    justify-content: flex-end;
+    padding-right: $euiSize;
+  }
+
   // ASSETS LIST
 
   .canvasAssetManager__asset {
@@ -34,6 +36,11 @@
     overflow: hidden; // hides image from outer panel boundaries
   }
 
+  .canvasAssetManager__emptyPanel {
+    max-width: 400px;
+    margin: 0 auto;
+  }
+
   .canvasAssetManager__thumb {
     margin: -$euiSizeS;
     margin-bottom: 0;
@@ -52,4 +59,8 @@
       opacity: 0; // only show the background image (which will properly keep proportions)
     }
   }
+
+  .canvasAssetManager__modalFooter {
+    justify-content: space-between;
+  }
 }
diff --git a/x-pack/plugins/canvas/public/components/asset_manager/index.js b/x-pack/plugins/canvas/public/components/asset_manager/index.js
index 2417e572e1a02b..878928a452c56a 100644
--- a/x-pack/plugins/canvas/public/components/asset_manager/index.js
+++ b/x-pack/plugins/canvas/public/components/asset_manager/index.js
@@ -6,14 +6,18 @@
 
 import { connect } from 'react-redux';
 import { compose, withProps } from 'recompose';
-import { set } from 'lodash';
+import { set, get } from 'lodash';
 import { fromExpression, toExpression } from '@kbn/interpreter/common';
 import { notify } from '../../lib/notify';
 import { getAssets } from '../../state/selectors/assets';
-import { removeAsset } from '../../state/actions/assets';
+import { removeAsset, createAsset } from '../../state/actions/assets';
 import { elementsRegistry } from '../../lib/elements_registry';
 import { addElement } from '../../state/actions/elements';
 import { getSelectedPage } from '../../state/selectors/workpad';
+import { encode } from '../../../common/lib/dataurl';
+import { getId } from '../../lib/get_id';
+import { findExistingAsset } from '../../lib/find_existing_asset';
+import { VALID_IMAGE_TYPES } from '../../../common/lib/constants';
 import { AssetManager as Component } from './asset_manager';
 
 const mapStateToProps = state => ({
@@ -44,15 +48,40 @@ const mapDispatchToProps = dispatch => ({
     imageElement.expression = toExpression(newAST);
     dispatch(addElement(pageId, imageElement));
   },
+  onAssetAdd: (type, content) => {
+    // make the ID here and pass it into the action
+    const assetId = getId('asset');
+    dispatch(createAsset(type, content, assetId));
+
+    // then return the id, so the caller knows the id that will be created
+    return assetId;
+  },
   removeAsset: assetId => dispatch(removeAsset(assetId)),
 });
 
 const mergeProps = (stateProps, dispatchProps, ownProps) => {
+  const { assets } = stateProps;
+  const { onAssetAdd } = dispatchProps;
   return {
     ...ownProps,
     ...stateProps,
     ...dispatchProps,
     addImageElement: dispatchProps.addImageElement(stateProps.selectedPage),
+    onAssetAdd: file => {
+      const [type, subtype] = get(file, 'type', '').split('/');
+      if (type === 'image' && VALID_IMAGE_TYPES.indexOf(subtype) >= 0) {
+        return encode(file).then(dataurl => {
+          const type = 'dataurl';
+          const existingId = findExistingAsset(type, dataurl, assets);
+          if (existingId) {
+            return existingId;
+          }
+          return onAssetAdd(type, dataurl);
+        });
+      }
+
+      return false;
+    },
   };
 };
 
diff --git a/x-pack/plugins/canvas/public/components/file_upload/file_upload.js b/x-pack/plugins/canvas/public/components/file_upload/file_upload.js
deleted file mode 100644
index 9640ab01bd158f..00000000000000
--- a/x-pack/plugins/canvas/public/components/file_upload/file_upload.js
+++ /dev/null
@@ -1,19 +0,0 @@
-/*
- * Copyright Elasticsearch B.V. and/or licensed to Elasticsearch B.V. under one
- * or more contributor license agreements. Licensed under the Elastic License;
- * you may not use this file except in compliance with the Elastic License.
- */
-
-import React from 'react';
-import PropTypes from 'prop-types';
-import { EuiFilePicker } from '@elastic/eui';
-
-export const FileUpload = ({ id = '', className = 'canvasFileUpload', onUpload }) => (
-  <EuiFilePicker compressed id={id} className={className} onChange={onUpload} />
-);
-
-FileUpload.propTypes = {
-  id: PropTypes.string,
-  className: PropTypes.string,
-  onUpload: PropTypes.func.isRequired,
-};
diff --git a/x-pack/plugins/canvas/public/components/function_form/index.js b/x-pack/plugins/canvas/public/components/function_form/index.js
index fbde896361cb63..5ca12b26e48c7e 100644
--- a/x-pack/plugins/canvas/public/components/function_form/index.js
+++ b/x-pack/plugins/canvas/public/components/function_form/index.js
@@ -21,6 +21,7 @@ import {
   getContextForIndex,
 } from '../../state/selectors/workpad';
 import { getAssets } from '../../state/selectors/assets';
+import { findExistingAsset } from '../../lib/find_existing_asset';
 import { FunctionForm as Component } from './function_form';
 
 const mapStateToProps = (state, { expressionIndex }) => ({
@@ -93,9 +94,7 @@ const mergeProps = (stateProps, dispatchProps, ownProps) => {
     onValueAdd: addArgument(element, pageId),
     onValueRemove: deleteArgument(element, pageId),
     onAssetAdd: (type, content) => {
-      const existingId = Object.keys(assets).find(
-        assetId => assets[assetId].type === type && assets[assetId].value === content
-      );
+      const existingId = findExistingAsset(type, content, assets);
       if (existingId) {
         return existingId;
       }
diff --git a/x-pack/plugins/canvas/public/components/workpad_header/index.js b/x-pack/plugins/canvas/public/components/workpad_header/index.js
index fec9c874744f33..e724b97b0bb4f5 100644
--- a/x-pack/plugins/canvas/public/components/workpad_header/index.js
+++ b/x-pack/plugins/canvas/public/components/workpad_header/index.js
@@ -9,7 +9,6 @@ import { connect } from 'react-redux';
 import { canUserWrite } from '../../state/selectors/app';
 import { getWorkpadName, getSelectedPage, isWriteable } from '../../state/selectors/workpad';
 import { setWriteable } from '../../state/actions/workpad';
-import { getAssets } from '../../state/selectors/assets';
 import { addElement } from '../../state/actions/elements';
 import { WorkpadHeader as Component } from './workpad_header';
 
@@ -18,7 +17,6 @@ const mapStateToProps = state => ({
   canUserWrite: canUserWrite(state),
   workpadName: getWorkpadName(state),
   selectedPage: getSelectedPage(state),
-  hasAssets: Object.keys(getAssets(state)).length ? true : false,
 });
 
 const mapDispatchToProps = dispatch => ({
diff --git a/x-pack/plugins/canvas/public/components/workpad_header/workpad_header.js b/x-pack/plugins/canvas/public/components/workpad_header/workpad_header.js
index c4fa1ce7062291..88f92f7eb69e6d 100644
--- a/x-pack/plugins/canvas/public/components/workpad_header/workpad_header.js
+++ b/x-pack/plugins/canvas/public/components/workpad_header/workpad_header.js
@@ -27,7 +27,6 @@ export const WorkpadHeader = ({
   isWriteable,
   canUserWrite,
   toggleWriteable,
-  hasAssets,
   addElement,
   setShowElementModal,
   showElementModal,
@@ -115,11 +114,9 @@ export const WorkpadHeader = ({
         {isWriteable ? (
           <EuiFlexItem grow={false}>
             <EuiFlexGroup alignItems="center" gutterSize="s">
-              {hasAssets && (
-                <EuiFlexItem grow={false}>
-                  <AssetManager />
-                </EuiFlexItem>
-              )}
+              <EuiFlexItem grow={false}>
+                <AssetManager />
+              </EuiFlexItem>
               <EuiFlexItem grow={false}>
                 <EuiButton
                   fill
@@ -141,7 +138,6 @@ export const WorkpadHeader = ({
 WorkpadHeader.propTypes = {
   isWriteable: PropTypes.bool,
   toggleWriteable: PropTypes.func,
-  hasAssets: PropTypes.bool,
   addElement: PropTypes.func.isRequired,
   showElementModal: PropTypes.bool,
   setShowElementModal: PropTypes.func,
diff --git a/x-pack/plugins/canvas/public/components/workpad_loader/workpad_loader.js b/x-pack/plugins/canvas/public/components/workpad_loader/workpad_loader.js
index 9008ae94a23249..bd01ec43228ce2 100644
--- a/x-pack/plugins/canvas/public/components/workpad_loader/workpad_loader.js
+++ b/x-pack/plugins/canvas/public/components/workpad_loader/workpad_loader.js
@@ -16,6 +16,7 @@ import {
   EuiButton,
   EuiToolTip,
   EuiEmptyPrompt,
+  EuiFilePicker,
 } from '@elastic/eui';
 import { sortByOrder } from 'lodash';
 import moment from 'moment';
@@ -25,7 +26,7 @@ import { Paginate } from '../paginate';
 import { WorkpadDropzone } from './workpad_dropzone';
 import { WorkpadCreate } from './workpad_create';
 import { WorkpadSearch } from './workpad_search';
-import { WorkpadUpload } from './workpad_upload';
+import { uploadWorkpad } from './upload_workpad';
 
 const formatDate = date => date && moment(date).format('MMM D, YYYY @ h:mma');
 
@@ -79,7 +80,7 @@ export class WorkpadLoader extends React.PureComponent {
   };
 
   // create new workpad from uploaded JSON
-  uploadWorkpad = async workpad => {
+  onUpload = async workpad => {
     this.setState({ createPending: true });
     await this.props.createWorkpad(workpad);
     this._isMounted && this.setState({ createPending: false });
@@ -232,7 +233,7 @@ export class WorkpadLoader extends React.PureComponent {
 
     return (
       <Fragment>
-        <WorkpadDropzone onUpload={this.uploadWorkpad} disabled={createPending || !canUserWrite}>
+        <WorkpadDropzone onUpload={this.onUpload} disabled={createPending || !canUserWrite}>
           <EuiBasicTable
             compressed
             items={rows}
@@ -294,7 +295,14 @@ export class WorkpadLoader extends React.PureComponent {
     );
 
     let uploadButton = (
-      <WorkpadUpload onUpload={this.uploadWorkpad} disabled={createPending || !canUserWrite} />
+      <EuiFilePicker
+        compressed
+        className="canvasWorkpad__upload--compressed"
+        initialPromptText="Import workpad JSON file"
+        onChange={([file]) => uploadWorkpad(file, this.onUpload)}
+        accept="application/json"
+        disabled={createPending || !canUserWrite}
+      />
     );
 
     if (!canUserWrite) {
diff --git a/x-pack/plugins/canvas/public/components/workpad_loader/workpad_upload.js b/x-pack/plugins/canvas/public/components/workpad_loader/workpad_upload.js
deleted file mode 100644
index 9c4372175b89ff..00000000000000
--- a/x-pack/plugins/canvas/public/components/workpad_loader/workpad_upload.js
+++ /dev/null
@@ -1,24 +0,0 @@
-/*
- * Copyright Elasticsearch B.V. and/or licensed to Elasticsearch B.V. under one
- * or more contributor license agreements. Licensed under the Elastic License;
- * you may not use this file except in compliance with the Elastic License.
- */
-
-import React from 'react';
-import PropTypes from 'prop-types';
-import { EuiFilePicker } from '@elastic/eui';
-import { uploadWorkpad } from './upload_workpad';
-
-export const WorkpadUpload = ({ onUpload, ...rest }) => (
-  <EuiFilePicker
-    {...rest}
-    compressed
-    className="canvasWorkpad__upload--compressed"
-    initialPromptText="Import workpad JSON file"
-    onChange={([file]) => uploadWorkpad(file, onUpload)}
-  />
-);
-
-WorkpadUpload.propTypes = {
-  onUpload: PropTypes.func.isRequired,
-};
diff --git a/x-pack/plugins/canvas/public/components/file_upload/index.js b/x-pack/plugins/canvas/public/lib/find_existing_asset.js
similarity index 52%
rename from x-pack/plugins/canvas/public/components/file_upload/index.js
rename to x-pack/plugins/canvas/public/lib/find_existing_asset.js
index 68c0f6150521b0..470d7797e6febd 100644
--- a/x-pack/plugins/canvas/public/components/file_upload/index.js
+++ b/x-pack/plugins/canvas/public/lib/find_existing_asset.js
@@ -4,4 +4,9 @@
  * you may not use this file except in compliance with the Elastic License.
  */
 
-export { FileUpload } from './file_upload';
+export const findExistingAsset = (type, content, assets) => {
+  const existingId = Object.keys(assets).find(
+    assetId => assets[assetId].type === type && assets[assetId].value === content
+  );
+  return existingId;
+};