diff --git a/package-lock.json b/package-lock.json
index c21bf873..0cd2583d 100644
--- a/package-lock.json
+++ b/package-lock.json
@@ -19206,9 +19206,9 @@
       }
     },
     "node_modules/vite/node_modules/rollup": {
-      "version": "3.29.4",
-      "resolved": "https://registry.npmjs.org/rollup/-/rollup-3.29.4.tgz",
-      "integrity": "sha512-oWzmBZwvYrU0iJHtDmhsm662rC15FRXmcjCk1xD771dFDx5jJ02ufAQQTn0etB2emNk4J9EZg/yWKpsn9BWGRw==",
+      "version": "3.29.5",
+      "resolved": "https://registry.npmjs.org/rollup/-/rollup-3.29.5.tgz",
+      "integrity": "sha512-GVsDdsbJzzy4S/v3dqWPJ7EfvZJfCHiDqe80IyrF59LYuP+e6U1LJoUqeuqRbwAWoMNoXivMNeNAOf5E22VA1w==",
       "dev": true,
       "bin": {
         "rollup": "dist/bin/rollup"
diff --git a/packages/chat-core/src/index.ts b/packages/chat-core/src/index.ts
index 6cff1555..bac45269 100644
--- a/packages/chat-core/src/index.ts
+++ b/packages/chat-core/src/index.ts
@@ -127,6 +127,10 @@ export interface BotResponseMetadata {
    * Whether the current conversation has been marked as incomprehension.
    */
   incomprehension?: boolean;
+  /**
+   * Upload URL's
+   */
+  uploadUrls: UploadUrl[];
   /**
    * Whether the client should poll for more bot responses.
    */
@@ -176,6 +180,20 @@ export interface BotMessage {
   selectedChoiceId?: string;
 }
 
+/**
+ * The upload destination for handling conversing with files
+ */
+export interface UploadUrl {
+  /**
+   * The URL of the upload
+   */
+  url: string;
+  /**
+   * The ID of the upload
+   */
+  uploadId: string;
+}
+
 /**
  * A choices to show to the user.
  */
@@ -401,6 +419,14 @@ export interface StructuredRequest {
    * The slots to populate
    */
   slots?: SlotsRecordOrArray;
+  /**
+   * Upload ID
+   */
+  uploadId?: string;
+  /**
+   * Upload utterance
+   */
+  utterance?: string;
   /**
    * @hidden
    * This is used internally to indicate that the client is polling the bot for more data.
diff --git a/packages/chat-widget/src/icons.tsx b/packages/chat-widget/src/icons.tsx
index 3c62c79e..d1450c30 100644
--- a/packages/chat-widget/src/icons.tsx
+++ b/packages/chat-widget/src/icons.tsx
@@ -24,14 +24,30 @@ export const ChatIcon = (): ReactNode => (
   </svg>
 );
 
+// eslint-disable-next-line jsdoc/require-returns
+/** @hidden @internal */
+export const CheckIcon = (): ReactNode => (
+  <svg viewBox="0 0 24 24" stroke="none" fill="currentColor">
+    <path d="M2.01 21 23 12 2.01 3 2 10l15 2-15 2z" />
+  </svg>
+);
+
 // eslint-disable-next-line jsdoc/require-returns
 /** @hidden @internal */
 export const SendIcon = (): ReactNode => (
-  <svg viewBox="0 0 360 360" stroke="none" fill="currentColor">
+  <svg viewBox="0 0 24 24" stroke="none" fill="currentColor">
     <path d="M2.01 21 23 12 2.01 3 2 10l15 2-15 2z" />
   </svg>
 );
 
+// eslint-disable-next-line jsdoc/require-returns
+/** @hidden @internal */
+export const AddPhotoIcon = (): ReactNode => (
+  <svg viewBox="0 0 24 24" stroke="none" fill="currentColor">
+    <path d="M19 7v2.99s-1.99.01-2 0V7h-3s.01-1.99 0-2h3V2h2v3h3v2zm-3 4V8h-3V5H5c-1.1 0-2 .9-2 2v12c0 1.1.9 2 2 2h12c1.1 0 2-.9 2-2v-8zM5 19l3-4 2 3 3-4 4 5z" />
+  </svg>
+);
+
 // eslint-disable-next-line jsdoc/require-returns
 /** @hidden @internal */
 export const DownloadIcon = (): ReactNode => (
diff --git a/packages/chat-widget/src/index.tsx b/packages/chat-widget/src/index.tsx
index fcc03eb2..9ada2ee1 100644
--- a/packages/chat-widget/src/index.tsx
+++ b/packages/chat-widget/src/index.tsx
@@ -18,7 +18,9 @@ import { ThemeProvider } from "@emotion/react";
 import { useChat, type ChatHook } from "@nlxai/chat-react";
 import {
   type Response,
+  type BotResponse,
   type ConversationHandler,
+  type UploadUrl,
   getCurrentExpirationTimestamp,
 } from "@nlxai/chat-core";
 import {
@@ -26,9 +28,11 @@ import {
   MinimizeIcon,
   ChatIcon,
   SendIcon,
+  CheckIcon,
+  AddPhotoIcon,
   ErrorOutlineIcon,
 } from "./icons";
-import { last, equals } from "ramda";
+import { last, equals, findLast } from "ramda";
 import * as constants from "./ui/constants";
 import {
   type Props,
@@ -352,6 +356,67 @@ const isInputDisabled = (responses: Response[]): boolean => {
   return new URLSearchParams(payload).get("nlx:input-disabled") === "true";
 };
 
+const findActiveUpload = (responses: Response[]): UploadUrl | null => {
+  const lastBotResponse = findLast(
+    (response): response is BotResponse => response.type === "bot",
+    responses,
+  );
+  if (lastBotResponse == null) {
+    return null;
+  }
+  return lastBotResponse.payload.metadata?.uploadUrls?.[0] ?? null;
+};
+
+interface ImageUploadProps {
+  upload: UploadUrl;
+}
+
+type UploadStatus = "empty" | "uploading" | "uploaded";
+
+const ImageUpload: FC<ImageUploadProps> = (props) => {
+  const [status, setStatus] = useState<UploadStatus>("empty");
+
+  if (status === "uploading") {
+    return <C.PendingMessageDots />;
+  }
+
+  if (status === "uploaded") {
+    <C.UploadSuccess>
+      <CheckIcon />
+    </C.UploadSuccess>;
+  }
+
+  return (
+    <C.UploadIconLabel>
+      <input
+        type="file"
+        onChange={async (ev) => {
+          const file = ev.target.files?.[0];
+          if (file == null) {
+            return;
+          }
+          setStatus("uploading");
+          const formData = new FormData();
+          formData.append("file", file);
+          try {
+            await fetch(props.upload.url, {
+              method: "PUT",
+              headers: {
+                "Content-Type": "image/jpeg",
+              },
+              body: formData,
+            });
+            setStatus("uploaded");
+          } catch (err) {
+            console.error(err);
+          }
+        }}
+      />
+      <AddPhotoIcon />
+    </C.UploadIconLabel>
+  );
+};
+
 /**
  * Hook to get the ConversationHandler for the widget.
  * This may be called before the Widget has been created.
@@ -546,9 +611,17 @@ export const Widget = forwardRef<WidgetRef, Props>(function Widget(props, ref) {
     scrollToBottom();
   }, [chat.responses]);
 
+  const activeUpload = findActiveUpload(chat.responses);
+
   const submit =
     chat.inputValue.replace(/ /gi, "") !== "" &&
     (() => {
+      if (activeUpload !== null) {
+        chat.conversationHandler.sendStructured({
+          uploadId: activeUpload.uploadId,
+          utterance: chat.inputValue,
+        });
+      }
       chat.conversationHandler.sendText(chat.inputValue);
       chat.setInputValue("");
     });
@@ -652,6 +725,9 @@ export const Widget = forwardRef<WidgetRef, Props>(function Widget(props, ref) {
                       }}
                     />
                     <C.BottomButtonsContainer>
+                      {activeUpload == null ? null : (
+                        <ImageUpload upload={activeUpload} />
+                      )}
                       <C.IconButton
                         disabled={Boolean(submit === false)}
                         onClick={() => {
diff --git a/packages/chat-widget/src/ui/components.tsx b/packages/chat-widget/src/ui/components.tsx
index 3fdc9aa4..47e9784c 100644
--- a/packages/chat-widget/src/ui/components.tsx
+++ b/packages/chat-widget/src/ui/components.tsx
@@ -358,6 +358,68 @@ export const IconButton = styled.button<{
   ${hoverBg}
 `;
 
+export const UploadIconLabel = styled.label<{
+  /** @hidden @internal */
+  disabled?: boolean;
+}>`
+  height: 35px;
+  width: 35px;
+  border-radius: 18px;
+  flex: none;
+  padding: 8px;
+  font-size: ${constants.fontSize}px;
+  ${(props) =>
+    props.disabled === true
+      ? `
+  opacity: 0.6;
+  `
+      : `
+  `}
+  border: 0;
+  box-shadow: none;
+  color: ${(props) => props.theme.primaryColor};
+  background: none;
+  position: relative;
+  cursor: pointer;
+
+  :focus {
+    outline: none;
+    ${(props) => focusShadow(props.theme)}
+  }
+
+  :disabled {
+    cursor: auto;
+  }
+
+  svg {
+    fill: ${(props) => props.theme.primaryColor};
+  }
+
+  input {
+    /** Screen-reader-only implementation */
+    position: absolute;
+    width: 1px;
+    height: 1px;
+    padding: 0;
+    margin: -1px;
+    overflow: hidden;
+    clip: rect(0, 0, 0, 0);
+    white-space: nowrap;
+    border-width: 0;
+  }
+
+  ${hoverBg}
+`;
+
+export const UploadSuccess = styled.div<{}>`
+  height: 35px;
+  width: 35px;
+  flex: none;
+  padding: 8px;
+  font-size: ${constants.fontSize}px;
+  color: green;
+`;
+
 export const BottomButtonsContainer = styled.div<{
   /**
    *
@@ -368,6 +430,8 @@ export const BottomButtonsContainer = styled.div<{
   top: 50%;
   right: ${(props) => `${props.theme.spacing}px`};
   transform: translate3d(0, -50%, 0);
+  display: flex;
+  align-items: center;
 `;
 
 export const Input = styled.input<{
@@ -463,6 +527,7 @@ interface PinBubbleProps {
    */
   onClick: () => void;
 }
+
 // eslint-disable-next-line jsdoc/require-returns, jsdoc/require-param
 /** @hidden @internal */
 export const PinBubble: React.FunctionComponent<PinBubbleProps> = (