diff --git a/frontend/src/api/threads.ts b/frontend/src/api/threads.ts
index 4e4e29c3..ffa1b879 100644
--- a/frontend/src/api/threads.ts
+++ b/frontend/src/api/threads.ts
@@ -1,4 +1,4 @@
-import { Chat } from "../hooks/useChatList.ts";
+import { Chat } from "../types";
 
 export async function getThread(threadId: string): Promise<Chat | null> {
   try {
diff --git a/frontend/src/components/Chat.tsx b/frontend/src/components/Chat.tsx
index b5a29ebf..796d99ed 100644
--- a/frontend/src/components/Chat.tsx
+++ b/frontend/src/components/Chat.tsx
@@ -2,7 +2,7 @@ import { useEffect, useRef } from "react";
 import { StreamStateProps } from "../hooks/useStreamState";
 import { useChatMessages } from "../hooks/useChatMessages";
 import TypingBox from "./TypingBox";
-import { Message } from "./Message";
+import { MessageViewer } from "./Message";
 import { ArrowDownCircleIcon } from "@heroicons/react/24/outline";
 import { MessageWithFiles } from "../utils/formTypes.ts";
 import { useParams } from "react-router-dom";
@@ -51,7 +51,7 @@ export function Chat(props: ChatProps) {
   return (
     <div className="flex-1 flex flex-col items-stretch pb-[76px] pt-2">
       {messages?.map((msg, i) => (
-        <Message
+        <MessageViewer
           {...msg}
           key={msg.id}
           runId={
diff --git a/frontend/src/components/Document.tsx b/frontend/src/components/Document.tsx
index 4960102b..c2b194c3 100644
--- a/frontend/src/components/Document.tsx
+++ b/frontend/src/components/Document.tsx
@@ -1,13 +1,25 @@
 import { useMemo, useState } from "react";
-import { cn } from "../utils/cn";
 import { ChevronDownIcon, ChevronRightIcon } from "@heroicons/react/24/outline";
+import { cn } from "../utils/cn";
+import { MessageDocument } from "../types";
+import { StringViewer } from "./String";
+
+function isValidHttpUrl(str: string) {
+  let url;
+
+  try {
+    url = new URL(str);
+  } catch (_) {
+    return false;
+  }
 
-export interface PageDocument {
-  page_content: string;
-  metadata: Record<string, unknown>;
+  return url.protocol === "http:" || url.protocol === "https:";
 }
 
-function PageDocument(props: { document: PageDocument; className?: string }) {
+function DocumentViewer(props: {
+  document: MessageDocument;
+  className?: string;
+}) {
   const [open, setOpen] = useState(false);
 
   const metadata = useMemo(() => {
@@ -46,28 +58,28 @@ function PageDocument(props: { document: PageDocument; className?: string }) {
         )}
         onClick={() => setOpen(true)}
       >
-        <ChevronRightIcon className="mt-1 h-4 w-4 text-gray-500" />
-        <span className="min-w-0 flex-grow basis-0 overflow-hidden text-ellipsis whitespace-nowrap text-left">
-          {props.document.page_content.trim().replace(/\n/g, " ")}
-        </span>
+        <ChevronRightIcon className="mt-[6px] h-4 w-4 text-gray-500" />
+        <StringViewer
+          className="min-w-0 flex-grow basis-0 overflow-hidden text-ellipsis whitespace-nowrap text-left max-w-none"
+          value={props.document.page_content.trim().replace(/\n/g, " ")}
+        />
       </button>
     );
   }
 
   return (
-    <button
+    <div
       className={cn(
         "flex items-start gap-4 px-4 text-left transition-colors hover:bg-gray-50/50 active:bg-gray-50",
         props.className,
       )}
-      onClick={() => setOpen(false)}
     >
-      <ChevronDownIcon className="mt-1 h-4 w-4 text-gray-500" />
+      <button onClick={() => setOpen(false)}>
+        <ChevronDownIcon className="mt-[6px] h-4 w-4 text-gray-500" />
+      </button>
 
       <span className="flex flex-grow basis-0 flex-col gap-4">
-        <span className="whitespace-pre-line">
-          {props.document.page_content}
-        </span>
+        <StringViewer value={props.document.page_content} />
 
         <span className="flex flex-col flex-wrap items-start gap-2">
           {metadata.map(({ key, value }, idx) => {
@@ -77,22 +89,28 @@ function PageDocument(props: { document: PageDocument; className?: string }) {
                 key={idx}
               >
                 <span className="mr-1.5 font-mono font-bold">{key}</span>
-                <span className="whitespace-pre-wrap">{value}</span>
+                {isValidHttpUrl(value) ? (
+                  <a href={value} target="_blank" rel="noreferrer">
+                    {value}
+                  </a>
+                ) : (
+                  <span className="whitespace-pre-wrap">{value}</span>
+                )}
               </span>
             );
           })}
         </span>
       </span>
-    </button>
+    </div>
   );
 }
 
-export function DocumentList(props: { documents: PageDocument[] }) {
+export function DocumentList(props: { documents: MessageDocument[] }) {
   return (
     <div className="flex flex-col items-stretch gap-4 rounded-lg ring-1 ring-gray-300 overflow-hidden my-2">
       <div className="grid divide-y empty:hidden">
         {props.documents.map((document, idx) => (
-          <PageDocument document={document} key={idx} className="py-3" />
+          <DocumentViewer document={document} key={idx} className="py-3" />
         ))}
       </div>
     </div>
diff --git a/frontend/src/components/Message.tsx b/frontend/src/components/Message.tsx
index d691b449..2f1d1785 100644
--- a/frontend/src/components/Message.tsx
+++ b/frontend/src/components/Message.tsx
@@ -1,12 +1,12 @@
 import { memo, useState } from "react";
-import { Message as MessageType } from "../hooks/useChatList";
+import { MessageDocument, Message as MessageType } from "../types";
 import { str } from "../utils/str";
 import { cn } from "../utils/cn";
-import { marked } from "marked";
-import DOMPurify from "dompurify";
 import { ChevronDownIcon } from "@heroicons/react/24/outline";
 import { LangSmithActions } from "./LangSmithActions";
 import { DocumentList } from "./Document";
+import { omit } from "lodash";
+import { StringViewer } from "./String";
 
 function tryJsonParse(value: string) {
   try {
@@ -88,14 +88,50 @@ function Function(props: {
   );
 }
 
-export const Message = memo(function Message(
+function isDocumentContent(
+  content: MessageType["content"],
+): content is MessageDocument[] {
+  return (
+    Array.isArray(content) &&
+    content.every((d) => typeof d === "object" && !!d && !!d.page_content)
+  );
+}
+
+export function MessageContent(props: { content: MessageType["content"] }) {
+  if (typeof props.content === "string") {
+    return <StringViewer value={props.content} />;
+  } else if (isDocumentContent(props.content)) {
+    return <DocumentList documents={props.content} />;
+  } else if (
+    Array.isArray(props.content) &&
+    props.content.every(
+      (it) => typeof it === "object" && !!it && typeof it.content === "string",
+    )
+  ) {
+    return (
+      <DocumentList
+        documents={props.content.map((it) => ({
+          page_content: it.content,
+          metadata: omit(it, "content"),
+        }))}
+      />
+    );
+  } else {
+    return <div className="text-gray-900 prose">{str(props.content)}</div>;
+  }
+}
+
+export const MessageViewer = memo(function (
   props: MessageType & { runId?: string },
 ) {
   const [open, setOpen] = useState(false);
   const contentIsDocuments =
     ["function", "tool"].includes(props.type) &&
-    Array.isArray(props.content) &&
-    props.content.every((d) => !!d.page_content);
+    isDocumentContent(props.content);
+  const showContent =
+    ["function", "tool"].includes(props.type) && !contentIsDocuments
+      ? open
+      : true;
   return (
     <div className="flex flex-col mb-8">
       <div className="leading-6 flex flex-row">
@@ -133,27 +169,7 @@ export const Message = memo(function Message(
                 args={call.function?.arguments}
               />
             ))}
-          {(
-            ["function", "tool"].includes(props.type) && !contentIsDocuments
-              ? open
-              : true
-          ) ? (
-            typeof props.content === "string" ? (
-              <div
-                className="text-gray-900 prose"
-                dangerouslySetInnerHTML={{
-                  __html: DOMPurify.sanitize(marked(props.content)).trim(),
-                }}
-              />
-            ) : contentIsDocuments ? (
-              // eslint-disable-next-line @typescript-eslint/no-explicit-any
-              <DocumentList documents={props.content as any} />
-            ) : (
-              <div className="text-gray-900 prose">{str(props.content)}</div>
-            )
-          ) : (
-            false
-          )}
+          {showContent && <MessageContent content={props.content} />}
         </div>
       </div>
       {props.runId && (
diff --git a/frontend/src/components/String.tsx b/frontend/src/components/String.tsx
new file mode 100644
index 00000000..b547e834
--- /dev/null
+++ b/frontend/src/components/String.tsx
@@ -0,0 +1,19 @@
+import { MarkedOptions, marked } from "marked";
+import DOMPurify from "dompurify";
+import { cn } from "../utils/cn";
+
+const OPTIONS: MarkedOptions = {
+  gfm: true,
+  breaks: true,
+};
+
+export function StringViewer(props: { value: string; className?: string }) {
+  return (
+    <div
+      className={cn("text-gray-900 prose", props.className)}
+      dangerouslySetInnerHTML={{
+        __html: DOMPurify.sanitize(marked(props.value, OPTIONS)).trim(),
+      }}
+    />
+  );
+}
diff --git a/frontend/src/components/TypingBox.tsx b/frontend/src/components/TypingBox.tsx
index c369c9d6..df463e05 100644
--- a/frontend/src/components/TypingBox.tsx
+++ b/frontend/src/components/TypingBox.tsx
@@ -12,7 +12,7 @@ import { useDropzone } from "react-dropzone";
 import { MessageWithFiles } from "../utils/formTypes.ts";
 import { DROPZONE_CONFIG, TYPE_NAME } from "../constants.ts";
 import { Config } from "../hooks/useConfigList.ts";
-import { Chat } from "../hooks/useChatList.ts";
+import { Chat } from "../types";
 
 function getFileTypeIcon(fileType: string) {
   switch (fileType) {
diff --git a/frontend/src/hooks/useChatList.ts b/frontend/src/hooks/useChatList.ts
index 2e3d4123..b5a51bb6 100644
--- a/frontend/src/hooks/useChatList.ts
+++ b/frontend/src/hooks/useChatList.ts
@@ -1,37 +1,6 @@
 import { useCallback, useEffect, useReducer } from "react";
 import orderBy from "lodash/orderBy";
-
-export interface Message {
-  id: string;
-  type: string;
-  content:
-    | string
-    | { page_content: string; metadata: Record<string, object> }[]
-    | object;
-  name?: string;
-  additional_kwargs?: {
-    name?: string;
-    function_call?: {
-      name?: string;
-      arguments?: string;
-    };
-    tool_calls?: {
-      id: string;
-      function?: {
-        name?: string;
-        arguments?: string;
-      };
-    }[];
-  };
-  example: boolean;
-}
-
-export interface Chat {
-  assistant_id: string;
-  thread_id: string;
-  name: string;
-  updated_at: string;
-}
+import { Chat } from "../types";
 
 export interface ChatListProps {
   chats: Chat[] | null;
diff --git a/frontend/src/hooks/useChatMessages.ts b/frontend/src/hooks/useChatMessages.ts
index 28830af3..40db07ed 100644
--- a/frontend/src/hooks/useChatMessages.ts
+++ b/frontend/src/hooks/useChatMessages.ts
@@ -1,5 +1,5 @@
 import { useEffect, useMemo, useRef, useState } from "react";
-import { Message } from "./useChatList";
+import { Message } from "../types";
 import { StreamState, mergeMessagesById } from "./useStreamState";
 
 async function getState(threadId: string) {
diff --git a/frontend/src/hooks/useStreamState.tsx b/frontend/src/hooks/useStreamState.tsx
index 960f2c26..f0a4baee 100644
--- a/frontend/src/hooks/useStreamState.tsx
+++ b/frontend/src/hooks/useStreamState.tsx
@@ -1,6 +1,6 @@
 import { useCallback, useState } from "react";
 import { fetchEventSource } from "@microsoft/fetch-event-source";
-import { Message } from "./useChatList";
+import { Message } from "../types";
 
 export interface StreamState {
   status: "inflight" | "error" | "done";
diff --git a/frontend/src/types.ts b/frontend/src/types.ts
new file mode 100644
index 00000000..f28259f5
--- /dev/null
+++ b/frontend/src/types.ts
@@ -0,0 +1,32 @@
+export interface FunctionDefinition {
+  name?: string;
+  arguments?: string;
+}
+
+export interface MessageDocument {
+  page_content: string;
+  metadata: Record<string, unknown>;
+}
+
+export interface Message {
+  id: string;
+  type: string;
+  content: string | MessageDocument[] | object;
+  name?: string;
+  additional_kwargs?: {
+    name?: string;
+    function_call?: FunctionDefinition;
+    tool_calls?: {
+      id: string;
+      function?: FunctionDefinition;
+    }[];
+  };
+  example: boolean;
+}
+
+export interface Chat {
+  assistant_id: string;
+  thread_id: string;
+  name: string;
+  updated_at: string;
+}