diff --git a/packages/netlify-cms-core/src/actions/mediaLibrary.ts b/packages/netlify-cms-core/src/actions/mediaLibrary.ts
index 144068a2..266a324c 100644
--- a/packages/netlify-cms-core/src/actions/mediaLibrary.ts
+++ b/packages/netlify-cms-core/src/actions/mediaLibrary.ts
@@ -413,6 +413,7 @@ function mediaLibraryOpened(payload: {
   forImage?: boolean;
   privateUpload?: boolean;
   value?: string;
+  replaceIndex?: number;
   allowMultiple?: boolean;
   config?: Map<string, unknown>;
   field?: EntryField;
diff --git a/packages/netlify-cms-core/src/reducers/mediaLibrary.ts b/packages/netlify-cms-core/src/reducers/mediaLibrary.ts
index 373f27a2..0a592dab 100644
--- a/packages/netlify-cms-core/src/reducers/mediaLibrary.ts
+++ b/packages/netlify-cms-core/src/reducers/mediaLibrary.ts
@@ -45,6 +45,8 @@ const defaultState: {
   files?: MediaFile[];
   config: Map<string, unknown>;
   field?: EntryField;
+  value?: string | string[];
+  replaceIndex?: number;
 } = {
   isVisible: false,
   showMediaButton: true,
@@ -62,7 +64,8 @@ function mediaLibrary(state = Map(defaultState), action: MediaLibraryAction) {
       });
 
     case MEDIA_LIBRARY_OPEN: {
-      const { controlID, forImage, privateUpload, config, field } = action.payload;
+      const { controlID, forImage, privateUpload, config, field, value, replaceIndex } =
+        action.payload;
       const libConfig = config || Map();
       const privateUploadChanged = state.get('privateUpload') !== privateUpload;
       if (privateUploadChanged) {
@@ -76,6 +79,8 @@ function mediaLibrary(state = Map(defaultState), action: MediaLibraryAction) {
           controlMedia: Map(),
           displayURLs: Map(),
           field,
+          value,
+          replaceIndex,
         });
       }
       return state.withMutations(map => {
@@ -86,6 +91,8 @@ function mediaLibrary(state = Map(defaultState), action: MediaLibraryAction) {
         map.set('privateUpload', privateUpload);
         map.set('config', libConfig);
         map.set('field', field);
+        map.set('value', value);
+        map.set('replaceIndex', replaceIndex);
       });
     }
 
@@ -95,8 +102,25 @@ function mediaLibrary(state = Map(defaultState), action: MediaLibraryAction) {
     case MEDIA_INSERT: {
       const { mediaPath } = action.payload;
       const controlID = state.get('controlID');
+      const value = state.get('value');
+
+      if (!Array.isArray(value)) {
+        return state.withMutations(map => {
+          map.setIn(['controlMedia', controlID], mediaPath);
+        });
+      }
+
+      const replaceIndex = state.get('replaceIndex');
+      const mediaArray = Array.isArray(mediaPath) ? mediaPath : [mediaPath];
+      const valueArray = value as string[];
+      if (typeof replaceIndex == 'number') {
+        valueArray[replaceIndex] = mediaArray[0];
+      } else {
+        valueArray.push(...mediaArray);
+      }
+
       return state.withMutations(map => {
-        map.setIn(['controlMedia', controlID], mediaPath);
+        map.setIn(['controlMedia', controlID], valueArray);
       });
     }
 
diff --git a/packages/netlify-cms-locales/src/en/index.js b/packages/netlify-cms-locales/src/en/index.js
index 555d4f4e..400eaf6b 100644
--- a/packages/netlify-cms-locales/src/en/index.js
+++ b/packages/netlify-cms-locales/src/en/index.js
@@ -169,19 +169,25 @@ const en = {
       },
       image: {
         choose: 'Choose an image',
+        chooseMultiple: 'Choose images',
         chooseUrl: 'Insert from URL',
         replaceUrl: 'Replace with URL',
         promptUrl: 'Enter the URL of the image',
         chooseDifferent: 'Choose different image',
+        addMore: 'Add more images',
         remove: 'Remove image',
+        removeAll: 'Remove all images',
       },
       file: {
         choose: 'Choose a file',
         chooseUrl: 'Insert from URL',
+        chooseMultiple: 'Choose files',
         replaceUrl: 'Replace with URL',
         promptUrl: 'Enter the URL of the file',
         chooseDifferent: 'Choose different file',
+        addMore: 'Add more files',
         remove: 'Remove file',
+        removeAll: 'Remove all files',
       },
       unknownControl: {
         noControl: "No control for widget '%{widget}'.",
diff --git a/packages/netlify-cms-widget-file/src/withFileControl.js b/packages/netlify-cms-widget-file/src/withFileControl.js
index 941b9c59..00932830 100644
--- a/packages/netlify-cms-widget-file/src/withFileControl.js
+++ b/packages/netlify-cms-widget-file/src/withFileControl.js
@@ -7,7 +7,15 @@ import { Map, List } from 'immutable';
 import { once } from 'lodash';
 import uuid from 'uuid/v4';
 import { oneLine } from 'common-tags';
-import { lengths, components, buttons, borders, effects, shadows } from 'netlify-cms-ui-default';
+import {
+  lengths,
+  components,
+  buttons,
+  borders,
+  effects,
+  shadows,
+  IconButton,
+} from 'netlify-cms-ui-default';
 import { basename } from 'netlify-cms-lib-util';
 import { SortableContainer, SortableElement } from 'react-sortable-hoc';
 import { arrayMoveImmutable as arrayMove } from 'array-move';
@@ -28,6 +36,15 @@ const ImageWrapper = styled.div`
   cursor: ${props => (props.sortable ? 'pointer' : 'auto')};
 `;
 
+const SortableImageButtonsWrapper = styled.div`
+  display: flex;
+  justify-content: center;
+  column-gap: 10px;
+  margin-right: 20px;
+  margin-top: -10px;
+  margin-bottom: 10px;
+`;
+
 const StyledImage = styled.img`
   width: 100%;
   height: 100%;
@@ -38,35 +55,55 @@ function Image(props) {
   return <StyledImage role="presentation" {...props} />;
 }
 
-const SortableImage = SortableElement(({ itemValue, getAsset, field }) => {
+function SortableImageButtons({ onRemove, onReplace }) {
   return (
-    <ImageWrapper sortable>
-      <Image src={getAsset(itemValue, field) || ''} />
-    </ImageWrapper>
+    <SortableImageButtonsWrapper>
+      <IconButton size="small" type="media" onClick={onReplace}></IconButton>
+      <IconButton size="small" type="close" onClick={onRemove}></IconButton>
+    </SortableImageButtonsWrapper>
   );
-});
+}
 
-const SortableMultiImageWrapper = SortableContainer(({ items, getAsset, field }) => {
+const SortableImage = SortableElement(({ itemValue, getAsset, field, onRemove, onReplace }) => {
   return (
-    <div
-      css={css`
-        display: flex;
-        flex-wrap: wrap;
-      `}
-    >
-      {items.map((itemValue, index) => (
-        <SortableImage
-          key={`item-${itemValue}`}
-          index={index}
-          itemValue={itemValue}
-          getAsset={getAsset}
-          field={field}
-        />
-      ))}
+    <div>
+      <ImageWrapper sortable>
+        <Image src={getAsset(itemValue, field) || ''} />
+      </ImageWrapper>
+      <SortableImageButtons
+        item={itemValue}
+        onRemove={onRemove}
+        onReplace={onReplace}
+      ></SortableImageButtons>
     </div>
   );
 });
 
+const SortableMultiImageWrapper = SortableContainer(
+  ({ items, getAsset, field, onRemoveOne, onReplaceOne }) => {
+    return (
+      <div
+        css={css`
+          display: flex;
+          flex-wrap: wrap;
+        `}
+      >
+        {items.map((itemValue, index) => (
+          <SortableImage
+            key={`item-${itemValue}`}
+            index={index}
+            itemValue={itemValue}
+            getAsset={getAsset}
+            field={field}
+            onRemove={onRemoveOne(index)}
+            onReplace={onReplaceOne(index)}
+          />
+        ))}
+      </div>
+    );
+  },
+);
+
 const FileLink = styled.a`
   margin-bottom: 20px;
   font-weight: normal;
@@ -102,6 +139,22 @@ function isMultiple(value) {
   return Array.isArray(value) || List.isList(value);
 }
 
+function sizeOfValue(value) {
+  if (Array.isArray(value)) {
+    return value.length;
+  }
+
+  if (List.isList(value)) {
+    return value.size;
+  }
+
+  return value ? 1 : 0;
+}
+
+function valueListToArray(value) {
+  return List.isList(value) ? value.toArray() : value;
+}
+
 const warnDeprecatedOptions = once(field =>
   console.warn(oneLine`
   Netlify CMS config: ${field.get('name')} field: property "options" has been deprecated for the
@@ -178,26 +231,13 @@ export default function withFileControl({ forImage } = {}) {
     handleChange = e => {
       const { field, onOpenMediaLibrary, value } = this.props;
       e.preventDefault();
-      let mediaLibraryFieldOptions;
-
-      /**
-       * `options` hash as a general field property is deprecated, only used
-       * when external media libraries were first introduced. Not to be
-       * confused with `options` for the select widget, which serves a different
-       * purpose.
-       */
-      if (field.hasIn(['options', 'media_library'])) {
-        warnDeprecatedOptions(field);
-        mediaLibraryFieldOptions = field.getIn(['options', 'media_library'], Map());
-      } else {
-        mediaLibraryFieldOptions = field.get('media_library', Map());
-      }
+      const mediaLibraryFieldOptions = this.getMediaLibraryFieldOptions();
 
       return onOpenMediaLibrary({
         controlID: this.controlID,
         forImage,
         privateUpload: field.get('private'),
-        value,
+        value: valueListToArray(value),
         allowMultiple: !!mediaLibraryFieldOptions.get('allow_multiple', true),
         config: mediaLibraryFieldOptions.get('config'),
         field,
@@ -218,6 +258,47 @@ export default function withFileControl({ forImage } = {}) {
       return this.props.onChange('');
     };
 
+    onRemoveOne = index => () => {
+      const { value } = this.props;
+      value.splice(index, 1);
+      return this.props.onChange(sizeOfValue(value) > 0 ? [...value] : null);
+    };
+
+    onReplaceOne = index => () => {
+      const { field, onOpenMediaLibrary, value } = this.props;
+      const mediaLibraryFieldOptions = this.getMediaLibraryFieldOptions();
+
+      return onOpenMediaLibrary({
+        controlID: this.controlID,
+        forImage,
+        privateUpload: field.get('private'),
+        value: valueListToArray(value),
+        replaceIndex: index,
+        allowMultiple: false,
+        config: mediaLibraryFieldOptions.get('config'),
+        field,
+      });
+    };
+
+    getMediaLibraryFieldOptions = () => {
+      const { field } = this.props;
+
+      if (field.hasIn(['options', 'media_library'])) {
+        warnDeprecatedOptions(field);
+        return field.getIn(['options', 'media_library'], Map());
+      }
+
+      return field.get('media_library', Map());
+    };
+
+    allowsMultiple = () => {
+      const mediaLibraryFieldOptions = this.getMediaLibraryFieldOptions();
+      return (
+        mediaLibraryFieldOptions.get('config', false) &&
+        mediaLibraryFieldOptions.get('config').get('multiple', false)
+      );
+    };
+
     onSortEnd = ({ oldIndex, newIndex }) => {
       const { value } = this.props;
       const newValue = arrayMove(value, oldIndex, newIndex);
@@ -274,6 +355,9 @@ export default function withFileControl({ forImage } = {}) {
           <SortableMultiImageWrapper
             items={value}
             onSortEnd={this.onSortEnd}
+            onRemoveOne={this.onRemoveOne}
+            onReplaceOne={this.onReplaceOne}
+            distance={4}
             getAsset={getAsset}
             field={field}
             axis="xy"
@@ -292,21 +376,26 @@ export default function withFileControl({ forImage } = {}) {
 
     renderSelection = subject => {
       const { t, field } = this.props;
+      const allowsMultiple = this.allowsMultiple();
       return (
         <div>
           {forImage ? this.renderImages() : null}
           <div>
             {forImage ? null : this.renderFileLinks()}
             <FileWidgetButton onClick={this.handleChange}>
-              {t(`editor.editorWidgets.${subject}.chooseDifferent`)}
+              {t(
+                `editor.editorWidgets.${subject}.${
+                  this.allowsMultiple() ? 'addMore' : 'chooseDifferent'
+                }`,
+              )}
             </FileWidgetButton>
-            {field.get('choose_url', true) ? (
+            {field.get('choose_url', true) && !this.allowsMultiple() ? (
               <FileWidgetButton onClick={this.handleUrl(subject)}>
                 {t(`editor.editorWidgets.${subject}.replaceUrl`)}
               </FileWidgetButton>
             ) : null}
             <FileWidgetButtonRemove onClick={this.handleRemove}>
-              {t(`editor.editorWidgets.${subject}.remove`)}
+              {t(`editor.editorWidgets.${subject}.remove${allowsMultiple ? 'All' : ''}`)}
             </FileWidgetButtonRemove>
           </div>
         </div>
@@ -318,7 +407,7 @@ export default function withFileControl({ forImage } = {}) {
       return (
         <>
           <FileWidgetButton onClick={this.handleChange}>
-            {t(`editor.editorWidgets.${subject}.choose`)}
+            {t(`editor.editorWidgets.${subject}.choose${this.allowsMultiple() ? 'Multiple' : ''}`)}
           </FileWidgetButton>
           {field.get('choose_url', true) ? (
             <FileWidgetButton onClick={this.handleUrl(subject)}>