diff --git a/packages/ui-core/src/components/FileDrop/README.md b/packages/ui-core/src/components/FileDrop/README.md
index 9f9b94cdd4..b658e8be19 100644
--- a/packages/ui-core/src/components/FileDrop/README.md
+++ b/packages/ui-core/src/components/FileDrop/README.md
@@ -29,13 +29,17 @@ example: true
 ### Accept
 
 The `accept` prop dictates what type of files are allowed. It can be an array or comma-separated string of
-[MIME type formats](https://en.wikipedia.org/wiki/Media_type#Common_examples) and/or file extensions
+[MIME type formats](https://en.wikipedia.org/wiki/Media_type#Common_examples) and/or file extensions.
+
+FileDrop accepts the same `messages` prop as the other Instructure UI input components for providing
+form validation feedback. If there are `error` messages in the `messages` array, FileDrop's border
+will turn the theme's `rejectedColor`.
 
 ```js
 ---
 example: true
 ---
-<Grid startAt="medium" vAlign="middle">
+<Grid startAt="medium">
   <GridRow>
     <GridCol>
 
@@ -43,6 +47,7 @@ example: true
         accept=".jpg"
         onDropAccepted={([file]) => { console.log(`File accepted ${file.name}`) }}
         onDropRejected={([file]) => { console.log(`File rejected ${file.name}`) }}
+        messages={[{ text: 'Invalid file type', type: 'error' }]}
         label={
           <Billboard
             size="small"
diff --git a/packages/ui-core/src/components/FileDrop/index.js b/packages/ui-core/src/components/FileDrop/index.js
index 447daa3f01..08fe9ef180 100644
--- a/packages/ui-core/src/components/FileDrop/index.js
+++ b/packages/ui-core/src/components/FileDrop/index.js
@@ -3,9 +3,13 @@ import PropTypes from 'prop-types'
 import classnames from 'classnames'
 
 import themeable from '@instructure/ui-themeable'
+import CustomPropTypes from '@instructure/ui-utils/lib/react/CustomPropTypes'
 import { omitProps } from '@instructure/ui-utils/lib/react/passthroughProps'
 import uid from '@instructure/ui-utils/lib/uid'
 
+import Container from '../Container'
+import FormFieldMessages from '../FormField/FormFieldMessages'
+
 import styles from './styles.css'
 import theme from './theme'
 
@@ -92,6 +96,13 @@ export default class FileDrop extends Component {
       PropTypes.arrayOf(PropTypes.string)
     ]),
     /**
+    * object with shape: `{
+    * text: PropTypes.string,
+    * type: PropTypes.oneOf(['error', 'hint', 'success', 'screenreader-only'])
+    *   }`
+    */
+    messages: PropTypes.arrayOf(CustomPropTypes.message),
+    /**
     * callback called when dropping files or when the file dialog window exits successfully
     */
     onDrop: PropTypes.func,
@@ -146,13 +157,15 @@ export default class FileDrop extends Component {
     enablePreview: false,
     allowMultiple: false,
     maxSize: Infinity,
-    minSize: 0
+    minSize: 0,
+    messages: []
   }
 
   constructor (props) {
     super(props)
 
     this.defaultId = `FileDrop__${uid()}`
+    this.messagesId = `FileDrop__messages-${uid()}`
   }
 
   state = {
@@ -165,6 +178,16 @@ export default class FileDrop extends Component {
   fileInputEl = null
   defaultId = null
 
+  get hasMessages () {
+    return this.props.messages && (this.props.messages.length > 0)
+  }
+
+  get invalid () {
+    return this.hasMessages && this.props.messages.findIndex((message) => {
+      return message.type === 'error'
+    }) >= 0
+  }
+
   getDataTransferItems (event, enablePreview) {
     let list = Array.prototype.slice.call(getEventFiles(event, this.fileInputEl))
     this.fileInputEl.value = null
@@ -325,7 +348,7 @@ export default class FileDrop extends Component {
     const id = this.props.id || this.defaultId
     const classes = {
       [styles.root]: true,
-      [styles.dragRejected]: this.state.isDragRejected,
+      [styles.dragRejected]: this.state.isDragRejected || this.invalid,
       [styles.dragAccepted]: this.state.isDragAccepted,
       [styles.focused]: this.state.focused
     }
@@ -342,7 +365,9 @@ export default class FileDrop extends Component {
           onDrop={this.handleDrop}
         >
           <span className={styles.label}>
-            {this.renderLabel()}
+            <span className={styles.layout}>
+              {this.renderLabel()}
+            </span>
           </span>
         </label>
         <input
@@ -357,7 +382,13 @@ export default class FileDrop extends Component {
           multiple={allowMultiple}
           accept={this.acceptStr()}
           onChange={this.handleDrop}
+          aria-describedby={this.hasMessages ? this.messagesId : null}
         />
+        {(this.hasMessages) ?
+          <Container display="block" margin="small 0 0">
+            <FormFieldMessages id={this.messagesId} messages={this.props.messages} />
+          </Container>
+        : null}
       </div>
     )
   }
diff --git a/packages/ui-core/src/components/FileDrop/styles.css b/packages/ui-core/src/components/FileDrop/styles.css
index b0de3af134..57275b9972 100644
--- a/packages/ui-core/src/components/FileDrop/styles.css
+++ b/packages/ui-core/src/components/FileDrop/styles.css
@@ -20,36 +20,63 @@
   box-sizing: border-box;
   position: relative;
   z-index: 1;
-  overflow: hidden;
   text-align: center;
   border-radius: var(--borderRadius);
-  border: var(--borderWidth) solid transparent;
+  border: var(--borderWidth) var(--borderStyle) transparent;
   cursor: pointer;
 
   &:hover {
     border-color: var(--hoverBorderColor);
-    border-style: var(--hoverBorderStyle);
+  }
+
+  &::before {
+    content: "";
+    position: absolute;
+    top: -0.25rem;
+    left: -0.25rem;
+    right: -0.25rem;
+    bottom: -0.25rem;
+    border: var(--focusBorderWidth) var(--focusBorderStyle) var(--focusBorderColor);
+    border-radius: var(--borderRadius);
+    opacity: 0;
+    transform: scale(0.01);
+    transition: all 0.2s;
   }
 }
 
+.layout {
+  display: block;
+  overflow: hidden;
+  border-radius: var(--borderRadius);
+}
+
 .focused {
-  .label {
-    border-color: var(--hoverBorderColor);
-    border-style: solid;
+  .label::before {
+    opacity: 1;
+    transform: scale(1);
   }
 }
 
-.dragAccepted,
-.dragRejected {
+.dragAccepted {
   .label {
-    border-style: var(--focusBorderStyle);
+    border-color: var(--acceptedColor);
   }
-}
 
-.dragAccepted .label {
-  border-color: var(--acceptedColor);
+  &.focused {
+    .label::before {
+      border-color: var(--acceptedColor);
+    }
+  }
 }
 
-.dragRejected .label {
-  border-color: var(--rejectedColor);
+.dragRejected {
+  .label {
+    border-color: var(--rejectedColor);
+  }
+
+  &.focused {
+    .label::before {
+      border-color: var(--rejectedColor);
+    }
+  }
 }
diff --git a/packages/ui-core/src/components/FileDrop/theme.js b/packages/ui-core/src/components/FileDrop/theme.js
index f24c5235a4..5909950446 100644
--- a/packages/ui-core/src/components/FileDrop/theme.js
+++ b/packages/ui-core/src/components/FileDrop/theme.js
@@ -3,9 +3,11 @@ export default function generator ({ borders, colors }) {
     backgroundColor: colors.white,
     borderRadius: borders.radiusLarge,
     borderWidth: borders.widthMedium,
+    borderStyle: 'dashed',
     hoverBorderColor: colors.brand,
-    hoverBorderStyle: 'dashed',
+    focusBorderWidth: borders.widthSmall,
     focusBorderStyle: 'solid',
+    focusBorderColor: colors.brand,
     acceptedColor: colors.brand,
     rejectedColor: colors.crimson
   }