diff --git a/web/src/app/chat/ChatPage.tsx b/web/src/app/chat/ChatPage.tsx
index 0a4d4ee24..a3239114a 100644
--- a/web/src/app/chat/ChatPage.tsx
+++ b/web/src/app/chat/ChatPage.tsx
@@ -964,6 +964,11 @@ export function ChatPage({
       (message) => message.messageId === messageIdToResend
     );
 
+    updateRegenerationState(
+      regenerationRequest
+        ? { regenerating: true, finalMessageIndex: messageIdToResend || 0 }
+        : null
+    );
     const messageMap = currentMessageMap(completeMessageDetail);
     const messageToResendParent =
       messageToResend?.parentMessageId !== null &&
@@ -991,12 +996,6 @@ export function ChatPage({
 
     setSubmittedMessage(currMessage);
 
-    updateRegenerationState(
-      regenerationRequest
-        ? { regenerating: true, finalMessageIndex: messageIdToResend || 0 }
-        : null
-    );
-
     updateChatState("loading");
 
     const currMessageHistory =
@@ -1811,9 +1810,14 @@ export function ChatPage({
                                 ? messageMap.get(message.parentMessageId)
                                 : null;
                               if (
-                                currentSessionRegenerationState?.regenerating &&
-                                message.messageId >
-                                  currentSessionRegenerationState?.finalMessageIndex!
+                                (currentSessionRegenerationState?.regenerating &&
+                                  message.messageId >
+                                    currentSessionRegenerationState?.finalMessageIndex!) ||
+                                (currentSessionChatState == "loading" &&
+                                  ((i >= messageHistory.length - 2 &&
+                                    message.type == "user") ||
+                                    (i >= messageHistory.length - 1 &&
+                                      !currentSessionRegenerationState?.regenerating)))
                               ) {
                                 return <></>;
                               }
@@ -1890,7 +1894,8 @@ export function ChatPage({
                                 if (
                                   currentSessionRegenerationState?.regenerating &&
                                   currentSessionChatState == "loading" &&
-                                  message.messageId == messageHistory.length - 1
+                                  (i == messageHistory.length - 1 ||
+                                    currentSessionRegenerationState?.regenerating)
                                 ) {
                                   return <></>;
                                 }
@@ -2093,17 +2098,17 @@ export function ChatPage({
                               }
                             })}
 
-                            {currentSessionChatState == "loading" ||
+                            {(currentSessionChatState == "loading" ||
                               (loadingError &&
                                 !currentSessionRegenerationState?.regenerating &&
                                 messageHistory[messageHistory.length - 1]
-                                  ?.type != "user" && (
-                                  <HumanMessage
-                                    key={-2}
-                                    messageId={-1}
-                                    content={submittedMessage}
-                                  />
-                                ))}
+                                  ?.type != "user")) && (
+                              <HumanMessage
+                                key={-2}
+                                messageId={-1}
+                                content={submittedMessage}
+                              />
+                            )}
 
                             {currentSessionChatState == "loading" && (
                               <div
diff --git a/web/src/app/chat/input/ChatInputBar.tsx b/web/src/app/chat/input/ChatInputBar.tsx
index 1a5ecb046..6ea2ce868 100644
--- a/web/src/app/chat/input/ChatInputBar.tsx
+++ b/web/src/app/chat/input/ChatInputBar.tsx
@@ -34,7 +34,6 @@ import { Hoverable } from "@/components/Hoverable";
 import { SettingsContext } from "@/components/settings/SettingsProvider";
 import { ChatState } from "../types";
 import UnconfiguredProviderText from "@/components/chat_search/UnconfiguredProviderText";
-import { useSearchContext } from "@/components/context/SearchContext";
 
 const MAX_INPUT_HEIGHT = 200;
 
diff --git a/web/src/app/chat/message/Messages.tsx b/web/src/app/chat/message/Messages.tsx
index 8cb51fee1..bbc4ae426 100644
--- a/web/src/app/chat/message/Messages.tsx
+++ b/web/src/app/chat/message/Messages.tsx
@@ -715,6 +715,7 @@ export const HumanMessage = ({
       // Move the cursor to the end of the text
       textareaRef.current.selectionStart = textareaRef.current.value.length;
       textareaRef.current.selectionEnd = textareaRef.current.value.length;
+      textareaRef.current.style.height = `${textareaRef.current.scrollHeight}px`;
     }
   }, [isEditing]);
 
@@ -787,6 +788,7 @@ export const HumanMessage = ({
                         style={{ scrollbarWidth: "thin" }}
                         onChange={(e) => {
                           setEditedContent(e.target.value);
+                          textareaRef.current!.style.height = "auto";
                           e.target.style.height = `${e.target.scrollHeight}px`;
                         }}
                         onKeyDown={(e) => {