diff --git a/pkg/interface/src/logic/lib/useDrag.ts b/pkg/interface/src/logic/lib/useDrag.ts
index 5b4878fb24..43072deca1 100644
--- a/pkg/interface/src/logic/lib/useDrag.ts
+++ b/pkg/interface/src/logic/lib/useDrag.ts
@@ -1,15 +1,39 @@
 import { useState, useCallback, useMemo, useEffect } from "react";
 
-function validateDragEvent(e: DragEvent): FileList | null {
-  const files = e.dataTransfer?.files;
-  console.log(files);
-  if(!files?.length) {
-    return null;
+function validateDragEvent(e: DragEvent): FileList | File[] | true | null {
+  const files: File[] = [];
+  let valid = false;
+  if (e.dataTransfer?.files) {
+    Array.from(e.dataTransfer.files).forEach(f => files.push(f));
   }
-  return files || null;
+  if (e.dataTransfer?.items) {
+    Array.from(e.dataTransfer.items || [])
+      .filter((i) => i.kind === 'file')
+      .forEach(f => {
+        valid = true; // Valid if file exists, but on DragOver, won't reveal its contents for security
+        const data = f.getAsFile();
+        if (data) {
+          files.push(data);
+        }
+      });
+  }
+  if (files.length) {
+    return [...new Set(files)];
+  }
+  if (navigator.userAgent.includes('Safari')) {
+    if (e.dataTransfer?.effectAllowed === 'all') {
+      valid = true;
+    } else if (e.dataTransfer?.files.length) {
+      return e.dataTransfer.files;
+    }
+  }
+  if (valid) {
+    return true;
+  }
+  return null;
 }
 
-export function useFileDrag(dragged: (f: FileList) => void) {
+export function useFileDrag(dragged: (f: FileList | File[]) => void) {
   const [dragging, setDragging] = useState(false);
 
   const onDragEnter = useCallback(
@@ -25,11 +49,11 @@ export function useFileDrag(dragged: (f: FileList) => void) {
   const onDrop = useCallback(
     (e: DragEvent) => {
       setDragging(false);
-      e.preventDefault();
       const files = validateDragEvent(e);
-      if (!files) {
+      if (!files || files === true) {
         return;
       }
+      e.preventDefault();
       dragged(files);
     },
     [setDragging, dragged]
@@ -37,6 +61,9 @@ export function useFileDrag(dragged: (f: FileList) => void) {
 
   const onDragOver = useCallback(
     (e: DragEvent) => {
+      if (!validateDragEvent(e)) {
+        return;
+      }
       e.preventDefault();
       setDragging(true);
     },
@@ -53,6 +80,18 @@ export function useFileDrag(dragged: (f: FileList) => void) {
     [setDragging]
   );
 
+  useEffect(() => {
+    const mouseleave = (e) => {
+      if (!e.relatedTarget && !e.toElement) {
+        setDragging(false);
+      }
+    };
+    document.body.addEventListener('mouseout', mouseleave);
+    return () => {
+      document.body.removeEventListener('mouseout', mouseleave);
+    }
+  }, [setDragging]);
+
   const bind = {
     onDragLeave,
     onDragOver,
diff --git a/pkg/interface/src/logic/lib/util.ts b/pkg/interface/src/logic/lib/util.ts
index 1ebe6e48ba..dc6cb6338c 100644
--- a/pkg/interface/src/logic/lib/util.ts
+++ b/pkg/interface/src/logic/lib/util.ts
@@ -353,4 +353,4 @@ export function usePreventWindowUnload(shouldPreventDefault: boolean, message =
 
 export function pluralize(text: string, isPlural = false, vowel = false) {
   return isPlural ? `${text}s`: `${vowel ? 'an' : 'a'} ${text}`;
-}
+}
\ No newline at end of file
diff --git a/pkg/interface/src/views/apps/chat/ChatResource.tsx b/pkg/interface/src/views/apps/chat/ChatResource.tsx
index 0d8c905f74..65171325b9 100644
--- a/pkg/interface/src/views/apps/chat/ChatResource.tsx
+++ b/pkg/interface/src/views/apps/chat/ChatResource.tsx
@@ -68,7 +68,7 @@ export function ChatResource(props: ChatResourceProps) {
   const chatInput = useRef<ChatInput>();
 
   const onFileDrag = useCallback(
-    (files: FileList) => {
+    (files: FileList | File[]) => {
       if (!chatInput.current) {
         return;
       }
diff --git a/pkg/interface/src/views/apps/chat/components/ChatInput.tsx b/pkg/interface/src/views/apps/chat/components/ChatInput.tsx
index 09ff23904d..fd6773a173 100644
--- a/pkg/interface/src/views/apps/chat/components/ChatInput.tsx
+++ b/pkg/interface/src/views/apps/chat/components/ChatInput.tsx
@@ -1,7 +1,7 @@
 import React, { Component } from 'react';
 import ChatEditor from './chat-editor';
 import { S3Upload } from '~/views/components/s3-upload' ;
-import { uxToHex } from '~/logic/lib/util';
+import { fileListFromFileArray, uxToHex } from '~/logic/lib/util';
 import { Sigil } from '~/logic/lib/sigil';
 import tokenizeMessage, { isUrl } from '~/logic/lib/tokenizeMessage';
 import GlobalApi from '~/logic/api/global';
@@ -150,16 +150,14 @@ export default class ChatInput extends Component<ChatInputProps, ChatInputState>
     this.uploadFiles(event.clipboardData.files);
   }
 
-  uploadFiles(files: FileList) {
+  uploadFiles(files: FileList | File[]) {
     if (!this.readyToUpload()) {
       return;
     }
-    if (!this.s3Uploader.current || !this.s3Uploader.current.inputRef.current)
-return;
-    this.s3Uploader.current.inputRef.current.files = files;
-    const fire = document.createEvent('HTMLEvents');
-    fire.initEvent('change', true, true);
-    this.s3Uploader.current?.inputRef.current?.dispatchEvent(fire);
+    if (!this.s3Uploader.current) {
+      return;
+    }
+    this.s3Uploader.current.uploadFiles(files);
   }
 
   render() {
diff --git a/pkg/interface/src/views/components/s3-upload.tsx b/pkg/interface/src/views/components/s3-upload.tsx
index d89ef154a9..89b7c06277 100644
--- a/pkg/interface/src/views/components/s3-upload.tsx
+++ b/pkg/interface/src/views/components/s3-upload.tsx
@@ -51,6 +51,7 @@ export class S3Upload extends Component<S3UploadProps, S3UploadState> {
     this.s3 = new S3Client();
     this.setCredentials(props.credentials, props.configuration);
     this.inputRef = React.createRef();
+    this.uploadFiles = this.uploadFiles.bind(this);
   }
 
   isReady(creds, config): boolean {
@@ -84,13 +85,9 @@ export class S3Upload extends Component<S3UploadProps, S3UploadState> {
     );
   }
 
-  onChange(): void {
+  uploadFiles(files: FileList | File[]) {
     const { props } = this;
-    if (!this.inputRef.current) { return; }
-    let files = this.inputRef.current.files;
-    if (!files || files.length <= 0) { return; }
-
-    let file = files.item(0);
+    let file = ('item' in files) ? files.item(0) : files[0];
     if (!file) { return; }
     const fileParts = file.name.split('.');
     const fileName = fileParts.slice(0, -1);
@@ -118,6 +115,13 @@ export class S3Upload extends Component<S3UploadProps, S3UploadState> {
     }, 200);
   }
 
+  onChange(): void {
+    if (!this.inputRef.current) { return; }
+    let files = this.inputRef.current.files;
+    if (!files || files.length <= 0) { return; }
+    this.uploadFiles(files);
+  }
+
   onClick() {
     if (!this.inputRef.current) { return; }
     this.inputRef.current.click();