diff --git a/ts/packages/shell/src/renderer/src/chatInput.ts b/ts/packages/shell/src/renderer/src/chatInput.ts
index 98b5266b..bbaed815 100644
--- a/ts/packages/shell/src/renderer/src/chatInput.ts
+++ b/ts/packages/shell/src/renderer/src/chatInput.ts
@@ -1,6 +1,7 @@
 // Copyright (c) Microsoft Corporation.
 // Licensed under the MIT License.
 
+import DOMPurify from "dompurify";
 import { _arrayBufferToBase64 } from "./chatView";
 import {
     iconMicrophone,
@@ -57,11 +58,12 @@ export class ExpandableTextarea {
             if (this.entryHandlers.onChange !== undefined) {
                 this.entryHandlers.onChange(this);
             }
-
+        });
+        this.textEntry.onchange = () => {
             if (sendButton !== undefined) {
                 sendButton.disabled = this.textEntry.innerHTML.length == 0;
             }
-        });
+        };
         this.textEntry.onwheel = (event) => {
             if (this.entryHandlers.onMouseWheel !== undefined) {
                 this.entryHandlers.onMouseWheel(this, event);
@@ -80,12 +82,14 @@ export class ExpandableTextarea {
 
         // Set the cursor to the end of the text
         const r = document.createRange();
-        r.setEnd(this.textEntry.childNodes[0], content?.length ?? 0);
-        r.collapse(false);
-        const s = document.getSelection();
-        if (s) {
-            s.removeAllRanges();
-            s.addRange(r);
+        if (this.textEntry.childNodes.length > 0) {
+            r.setEnd(this.textEntry.childNodes[0], content?.length ?? 0);
+            r.collapse(false);
+            const s = document.getSelection();
+            if (s) {
+                s.removeAllRanges();
+                s.addRange(r);
+            }
         }
     }
 
@@ -187,6 +191,12 @@ export class ChatInput {
             this.sendButton,
         );
 
+        this.textarea.getTextEntry().onpaste = (e: ClipboardEvent) => {
+            if (e.clipboardData !== null) {
+                this.getTextFromDataTransfer(e.clipboardData);
+            }
+        };
+
         this.textarea.getTextEntry().ondragenter = (e: DragEvent) => {
             if (!this.dragEnabled) {
                 return;
@@ -201,7 +211,8 @@ export class ChatInput {
 
             console.log("enter " + this.dragTemp);
 
-            this.textarea.getTextEntry().innerText = "Drop image files here...";
+            this.textarea.getTextEntry().innerText =
+                "Drop image files or text here...";
             this.textarea.getTextEntry().classList.add("chat-input-drag");
         };
 
@@ -237,8 +248,8 @@ export class ChatInput {
 
             this.dragTemp = undefined;
 
-            if (e.dataTransfer != null && e.dataTransfer.files.length > 0) {
-                this.loadImageFile(e.dataTransfer.files[0]);
+            if (e.dataTransfer != null) {
+                this.getTextFromDataTransfer(e.dataTransfer);
             }
 
             e.preventDefault();
@@ -378,4 +389,37 @@ export class ChatInput {
     public focus() {
         this.textarea.focus();
     }
+
+    /**
+     * Takes dataTransfer and gets a plain text representation from the data there
+     * and loads it into the input box
+     *
+     * @param dataTransfer The dataTransfer object from drag/drop/paste events
+     */
+    public getTextFromDataTransfer(dataTransfer: DataTransfer) {
+        if (dataTransfer.files.length > 0) {
+            this.loadImageFile(dataTransfer.files[0]);
+        } else if (dataTransfer.items.length > 0) {
+            let index: number = dataTransfer.types.indexOf("text/plain");
+            let plainText: boolean = true;
+            if (index === -1) {
+                index = dataTransfer.types.indexOf("text/html");
+                plainText = false;
+            }
+
+            if (index === -1) {
+                this.textarea.getTextEntry().innerText = `Unsupported drag/drop data type '${dataTransfer.types.join(", ")}'`;
+            } else {
+                dataTransfer.items[index].getAsString((s) => {
+                    if (plainText) {
+                        this.textarea.getTextEntry().innerText = s;
+                    } else {
+                        // strip out all HTML from supplied input
+                        this.textarea.getTextEntry().innerText +=
+                            DOMPurify.sanitize(s, { ALLOWED_TAGS: [] });
+                    }
+                });
+            }
+        }
+    }
 }
diff --git a/ts/packages/shell/src/renderer/src/chatView.ts b/ts/packages/shell/src/renderer/src/chatView.ts
index 1f6f3771..304638d8 100644
--- a/ts/packages/shell/src/renderer/src/chatView.ts
+++ b/ts/packages/shell/src/renderer/src/chatView.ts
@@ -71,7 +71,7 @@ export class ChatView {
     chatInput: ChatInput;
     private partialCompletion: PartialCompletion | undefined;
 
-    private commandBackStack: (string | null)[] = [];
+    private commandBackStack: string[] = [];
     private commandBackStackIndex = 0;
 
     private hideMetrics = true;
@@ -109,8 +109,9 @@ export class ChatView {
                 // history
                 if (!ev.altKey && !ev.ctrlKey) {
                     if (ev.key == "ArrowUp" || ev.key == "ArrowDown") {
-                        const currentContent =
-                            this.chatInput.textarea.getTextEntry().textContent;
+                        const currentContent: string =
+                            this.chatInput.textarea.getTextEntry().innerHTML ??
+                            "";
 
                         if (
                             this.commandBackStack.length === 0 ||
@@ -118,16 +119,22 @@ export class ChatView {
                                 this.commandBackStackIndex
                             ] !== currentContent
                         ) {
-                            const messages = this.messageDiv.querySelectorAll(
-                                ".chat-message-user:not(.chat-message-hidden) .chat-message-content",
-                            );
+                            const messages: NodeListOf<Element> =
+                                this.messageDiv.querySelectorAll(
+                                    ".chat-message-container-user:not(.chat-message-hidden) .chat-message-content",
+                                );
                             this.commandBackStack = Array.from(messages).map(
-                                (m) => m.textContent,
+                                (m: Element) =>
+                                    m.firstElementChild?.innerHTML.replace(
+                                        'class="chat-input-image"',
+                                        'class="chat-input-dropImage"',
+                                    ) ?? "",
                             );
 
                             this.commandBackStack.unshift(currentContent);
                             this.commandBackStackIndex = 0;
                         }
+
                         if (
                             ev.key == "ArrowUp" &&
                             this.commandBackStackIndex <
@@ -143,7 +150,8 @@ export class ChatView {
 
                         const content =
                             this.commandBackStack[this.commandBackStackIndex];
-                        this.chatInput.textarea.setContent(content);
+                        this.chatInput.textarea.getTextEntry().innerHTML =
+                            content;
 
                         return false;
                     }