diff --git a/common/comment.ts b/common/comment.ts
index 0d0c4daf..a217b292 100644
--- a/common/comment.ts
+++ b/common/comment.ts
@@ -1,3 +1,5 @@
+import type { JSONContent } from '@tiptap/core'
+
 // Currently, comments are created after the bet, not atomically with the bet.
 // They're uniquely identified by the pair contractId/betId.
 export type Comment = {
@@ -9,7 +11,9 @@ export type Comment = {
   replyToCommentId?: string
   userId: string
 
-  text: string
+  /** @deprecated - content now stored as JSON in content*/
+  text?: string
+  content: JSONContent
   createdTime: number
 
   // Denormalized, for rendering comments
diff --git a/web/components/comments-list.tsx b/web/components/comments-list.tsx
index f8e1d7e1..912023ad 100644
--- a/web/components/comments-list.tsx
+++ b/web/components/comments-list.tsx
@@ -10,6 +10,7 @@ import { User } from 'common/user'
 import { Col } from './layout/col'
 import { Linkify } from './linkify'
 import { groupBy } from 'lodash'
+import { Content } from './editor'
 
 export function UserCommentsList(props: {
   user: User
@@ -50,7 +51,8 @@ export function UserCommentsList(props: {
 
 function ProfileComment(props: { comment: Comment; className?: string }) {
   const { comment, className } = props
-  const { text, userUsername, userName, userAvatarUrl, createdTime } = comment
+  const { text, content, userUsername, userName, userAvatarUrl, createdTime } =
+    comment
   // TODO: find and attach relevant bets by comment betId at some point
   return (
     <Row className={className}>
@@ -64,7 +66,7 @@ function ProfileComment(props: { comment: Comment; className?: string }) {
           />{' '}
           <RelativeTimestamp time={createdTime} />
         </p>
-        <Linkify text={text} />
+        <Content content={content || text} />
       </div>
     </Row>
   )
diff --git a/web/components/editor.tsx b/web/components/editor.tsx
index 963cea7e..868c2129 100644
--- a/web/components/editor.tsx
+++ b/web/components/editor.tsx
@@ -41,14 +41,16 @@ export function useTextEditor(props: {
   max?: number
   defaultValue?: Content
   disabled?: boolean
+  simple?: boolean
 }) {
-  const { placeholder, max, defaultValue = '', disabled } = props
+  const { placeholder, max, defaultValue = '', disabled, simple } = props
 
   const users = useUsers()
 
   const editorClass = clsx(
     proseClass,
-    'min-h-[6em] resize-none outline-none border-none pt-3 px-4 focus:ring-0'
+    !simple && 'min-h-[6em]',
+    'resize-none outline-none border-none pt-3 px-4 focus:ring-0'
   )
 
   const editor = useEditor(
@@ -56,7 +58,8 @@ export function useTextEditor(props: {
       editorProps: { attributes: { class: editorClass } },
       extensions: [
         StarterKit.configure({
-          heading: { levels: [1, 2, 3] },
+          heading: simple ? false : { levels: [1, 2, 3] },
+          horizontalRule: simple ? false : {},
         }),
         Placeholder.configure({
           placeholder,
diff --git a/web/components/feed/feed-answer-comment-group.tsx b/web/components/feed/feed-answer-comment-group.tsx
index aabb1081..ee7b1695 100644
--- a/web/components/feed/feed-answer-comment-group.tsx
+++ b/web/components/feed/feed-answer-comment-group.tsx
@@ -72,7 +72,7 @@ export function FeedAnswerCommentGroup(props: {
     (comment?: Comment, answer?: Answer) => {
       setReplyToUsername(comment?.userUsername ?? answer?.username ?? '')
       setShowReply(true)
-      inputRef?.focus()
+      // TODO: focus
     }
   )
 
@@ -80,7 +80,7 @@ export function FeedAnswerCommentGroup(props: {
     // Only show one comment input for a bet at a time
     if (
       betsByCurrentUser.length > 1 &&
-      inputRef?.textContent?.length === 0 &&
+      // inputRef?.textContent?.length === 0 && //TODO: editor.isEmpty
       betsByCurrentUser.sort((a, b) => b.createdTime - a.createdTime)[0]
         ?.outcome !== answer.number.toString()
     )
@@ -173,7 +173,6 @@ export function FeedAnswerCommentGroup(props: {
             commentsByCurrentUser={commentsByCurrentUser}
             parentAnswerOutcome={answer.number.toString()}
             replyToUsername={replyToUsername}
-            setRef={setInputRef}
             onSubmitComment={() => {
               setShowReply(false)
               setReplyToUsername('')
diff --git a/web/components/feed/feed-comments.tsx b/web/components/feed/feed-comments.tsx
index f4c6eb74..cb6cc798 100644
--- a/web/components/feed/feed-comments.tsx
+++ b/web/components/feed/feed-comments.tsx
@@ -19,8 +19,6 @@ import {
   createCommentOnContract,
   MAX_COMMENT_LENGTH,
 } from 'web/lib/firebase/comments'
-import Textarea from 'react-expanding-textarea'
-import { Linkify } from 'web/components/linkify'
 import { SiteLink } from 'web/components/site-link'
 import { BetStatusText } from 'web/components/feed/feed-bets'
 import { Col } from 'web/components/layout/col'
@@ -28,10 +26,11 @@ import { getProbability } from 'common/calculate'
 import { LoadingIndicator } from 'web/components/loading-indicator'
 import { PaperAirplaneIcon } from '@heroicons/react/outline'
 import { track } from 'web/lib/service/analytics'
-import { useEvent } from 'web/hooks/use-event'
 import { Tipper } from '../tipper'
 import { CommentTipMap, CommentTips } from 'web/hooks/use-tip-txns'
 import { useWindowSize } from 'web/hooks/use-window-size'
+import { Content, TextEditor, useTextEditor } from '../editor'
+import { Editor, JSONContent } from '@tiptap/react'
 
 export function FeedCommentThread(props: {
   contract: Contract
@@ -60,15 +59,13 @@ export function FeedCommentThread(props: {
       parentComment.id && comment.replyToCommentId === parentComment.id
   )
   commentsList.unshift(parentComment)
-  const [inputRef, setInputRef] = useState<HTMLTextAreaElement | null>(null)
+
   function scrollAndOpenReplyInput(comment: Comment) {
     setReplyToUsername(comment.userUsername)
     setShowReply(true)
-    inputRef?.focus()
+    //TODO focus
   }
-  useEffect(() => {
-    if (showReply && inputRef) inputRef.focus()
-  }, [inputRef, showReply])
+
   return (
     <Col className={'w-full gap-3 pr-1'}>
       <span
@@ -100,7 +97,6 @@ export function FeedCommentThread(props: {
             parentCommentId={parentComment.id}
             replyToUsername={replyToUsername}
             parentAnswerOutcome={comments[0].answerOutcome}
-            setRef={setInputRef}
             onSubmitComment={() => {
               setShowReply(false)
               setReplyToUsername('')
@@ -195,7 +191,8 @@ export function FeedComment(props: {
     truncate,
     onReplyClick,
   } = props
-  const { text, userUsername, userName, userAvatarUrl, createdTime } = comment
+  const { text, content, userUsername, userName, userAvatarUrl, createdTime } =
+    comment
   let betOutcome: string | undefined,
     bought: string | undefined,
     money: string | undefined
@@ -277,7 +274,7 @@ export function FeedComment(props: {
           />
         </div>
         <TruncatedComment
-          comment={text}
+          comment={content || text}
           moreHref={contractPath(contract)}
           shouldTruncate={truncate}
         />
@@ -346,7 +343,6 @@ export function CommentInput(props: {
   betsByCurrentUser: Bet[]
   commentsByCurrentUser: Comment[]
   replyToUsername?: string
-  setRef?: (ref: HTMLTextAreaElement) => void
   // Reply to a free response answer
   parentAnswerOutcome?: string
   // Reply to another comment
@@ -361,10 +357,16 @@ export function CommentInput(props: {
     parentCommentId,
     replyToUsername,
     onSubmitComment,
-    setRef,
   } = props
   const user = useUser()
-  const [comment, setComment] = useState('')
+  const { editor, upload } = useTextEditor({
+    simple: true,
+    max: MAX_COMMENT_LENGTH,
+    placeholder:
+      !!parentCommentId || !!parentAnswerOutcome
+        ? 'Write a reply...'
+        : 'Write a comment...',
+  })
   const [isSubmitting, setIsSubmitting] = useState(false)
 
   const mostRecentCommentableBet = getMostRecentCommentableBet(
@@ -380,18 +382,17 @@ export function CommentInput(props: {
       track('sign in to comment')
       return await firebaseLogin()
     }
-    if (!comment || isSubmitting) return
+    if (!editor || editor.isEmpty || isSubmitting) return
     setIsSubmitting(true)
     await createCommentOnContract(
       contract.id,
-      comment,
+      editor.getJSON(),
       user,
       betId,
       parentAnswerOutcome,
       parentCommentId
     )
     onSubmitComment?.()
-    setComment('')
     setIsSubmitting(false)
   }
 
@@ -446,14 +447,12 @@ export function CommentInput(props: {
                 )}
             </div>
             <CommentInputTextArea
-              commentText={comment}
-              setComment={setComment}
-              isReply={!!parentCommentId || !!parentAnswerOutcome}
+              editor={editor}
+              upload={upload}
               replyToUsername={replyToUsername ?? ''}
               user={user}
               submitComment={submitComment}
               isSubmitting={isSubmitting}
-              setRef={setRef}
               presetId={id}
             />
           </div>
@@ -465,81 +464,43 @@ export function CommentInput(props: {
 
 export function CommentInputTextArea(props: {
   user: User | undefined | null
-  isReply: boolean
   replyToUsername: string
-  commentText: string
-  setComment: (text: string) => void
+  editor: Editor | null
+  upload: any
   submitComment: (id?: string) => void
   isSubmitting: boolean
-  setRef?: (ref: HTMLTextAreaElement) => void
   presetId?: string
-  enterToSubmitOnDesktop?: boolean
 }) {
   const {
-    isReply,
-    setRef,
     user,
-    commentText,
-    setComment,
+    editor,
+    upload,
     submitComment,
     presetId,
     isSubmitting,
     replyToUsername,
-    enterToSubmitOnDesktop,
   } = props
   const { width } = useWindowSize()
-  const memoizedSetComment = useEvent(setComment)
   useEffect(() => {
-    if (!replyToUsername || !user || replyToUsername === user.username) return
-    const replacement = `@${replyToUsername} `
-    memoizedSetComment(replacement + commentText.replace(replacement, ''))
-    // eslint-disable-next-line react-hooks/exhaustive-deps
-  }, [user, replyToUsername, memoizedSetComment])
+    editor?.setEditable(!isSubmitting)
+  }, [isSubmitting, editor])
+
+  // TODO: make at mention show up at beginning
   return (
     <>
       <Row className="gap-1.5 text-gray-700">
-        <Textarea
-          ref={setRef}
-          value={commentText}
-          onChange={(e) => setComment(e.target.value)}
-          className={clsx('textarea textarea-bordered w-full resize-none')}
-          // Make room for floating submit button.
-          style={{ paddingRight: 48 }}
-          placeholder={
-            isReply
-              ? 'Write a reply... '
-              : enterToSubmitOnDesktop
-              ? 'Send a message'
-              : 'Write a comment...'
-          }
-          autoFocus={false}
-          maxLength={MAX_COMMENT_LENGTH}
-          disabled={isSubmitting}
-          onKeyDown={(e) => {
-            if (
-              (enterToSubmitOnDesktop &&
-                e.key === 'Enter' &&
-                !e.shiftKey &&
-                width &&
-                width > 768) ||
-              (e.key === 'Enter' && (e.ctrlKey || e.metaKey))
-            ) {
-              e.preventDefault()
-              submitComment(presetId)
-              e.currentTarget.blur()
-            }
-          }}
-        />
-
+        <TextEditor editor={editor} upload={upload} />
         <Col className={clsx('relative justify-end')}>
           {user && !isSubmitting && (
             <button
               className={clsx(
                 'btn btn-ghost btn-sm absolute right-2 bottom-2 flex-row pl-2 capitalize',
-                !commentText && 'pointer-events-none text-gray-500'
+                (!editor || editor.isEmpty) &&
+                  'pointer-events-none text-gray-500'
               )}
               onClick={() => {
                 submitComment(presetId)
+                editor?.commands.clearContent()
               }}
             >
               <PaperAirplaneIcon
@@ -568,28 +529,22 @@ export function CommentInputTextArea(props: {
 }
 
 export function TruncatedComment(props: {
-  comment: string
+  comment: JSONContent
   moreHref: string
   shouldTruncate?: boolean
 }) {
   const { comment, moreHref, shouldTruncate } = props
   let truncated = comment
 
-  // Keep descriptions to at most 400 characters
+  // TODO: Keep descriptions to at most 80 words (~400 characters)
   const MAX_CHARS = 400
-  if (shouldTruncate && truncated.length > MAX_CHARS) {
-    truncated = truncated.slice(0, MAX_CHARS)
-    // Make sure to end on a space
-    const i = truncated.lastIndexOf(' ')
-    truncated = truncated.slice(0, i)
-  }
 
   return (
     <div
       className="mt-2 whitespace-pre-line break-words text-gray-700"
       style={{ fontSize: 15 }}
     >
-      <Linkify text={truncated} />
+      <Content content={comment} />
       {truncated != comment && (
         <SiteLink href={moreHref} className="text-indigo-700">
           ... (show more)
diff --git a/web/components/groups/group-chat.tsx b/web/components/groups/group-chat.tsx
index 2cf2d73d..1a8d1175 100644
--- a/web/components/groups/group-chat.tsx
+++ b/web/components/groups/group-chat.tsx
@@ -23,6 +23,7 @@ import { Tipper } from 'web/components/tipper'
 import { sum } from 'lodash'
 import { formatMoney } from 'common/util/format'
 import { useWindowSize } from 'web/hooks/use-window-size'
+import { useTextEditor } from '../editor'
 
 export function GroupChat(props: {
   messages: Comment[]
@@ -31,7 +32,10 @@ export function GroupChat(props: {
   tips: CommentTipMap
 }) {
   const { messages, user, group, tips } = props
-  const [messageText, setMessageText] = useState('')
+  const { editor, upload } = useTextEditor({
+    simple: true,
+    placeholder: 'Send a message',
+  })
   const [isSubmitting, setIsSubmitting] = useState(false)
   const [scrollToBottomRef, setScrollToBottomRef] =
     useState<HTMLDivElement | null>(null)
@@ -39,30 +43,30 @@ export function GroupChat(props: {
   const [scrollToMessageRef, setScrollToMessageRef] =
     useState<HTMLDivElement | null>(null)
   const [replyToUsername, setReplyToUsername] = useState('')
-  const [inputRef, setInputRef] = useState<HTMLTextAreaElement | null>(null)
-  const [groupedMessages, setGroupedMessages] = useState<Comment[]>([])
+
   const router = useRouter()
   const isMember = user && group.memberIds.includes(user?.id)
 
-  useMemo(() => {
+  // array of groups, where each group is an array of messages that are displayed as one
+  const groupedMessages = useMemo(() => {
     // Group messages with createdTime within 2 minutes of each other.
-    const tempMessages = []
+    const tempGrouped: Comment[][] = []
     for (let i = 0; i < messages.length; i++) {
       const message = messages[i]
-      if (i === 0) tempMessages.push({ ...message })
+      if (i === 0) tempGrouped.push([message])
       else {
         const prevMessage = messages[i - 1]
         const diff = message.createdTime - prevMessage.createdTime
         const creatorsMatch = message.userId === prevMessage.userId
         if (diff < 2 * 60 * 1000 && creatorsMatch) {
-          tempMessages[tempMessages.length - 1].text += `\n${message.text}`
+          tempGrouped.at(-1)?.push(message)
         } else {
-          tempMessages.push({ ...message })
+          tempGrouped.push([message])
         }
       }
     }
 
-    setGroupedMessages(tempMessages)
+    return tempGrouped
   }, [messages])
 
   useEffect(() => {
@@ -90,16 +94,16 @@ export function GroupChat(props: {
       track('sign in to comment')
       return await firebaseLogin()
     }
-    if (!messageText || isSubmitting) return
+    if (!editor || editor.isEmpty || isSubmitting) return
     setIsSubmitting(true)
-    await createCommentOnGroup(group.id, messageText, user)
-    setMessageText('')
+    await createCommentOnGroup(group.id, editor.getJSON(), user)
+    editor.commands.clearContent()
     setIsSubmitting(false)
     setReplyToUsername('')
-    inputRef?.focus()
+    focusInput()
   }
   function focusInput() {
-    inputRef?.focus()
+    editor?.commands.focus()
   }
 
   const { width, height } = useWindowSize()
@@ -119,20 +123,20 @@ export function GroupChat(props: {
         }
         ref={setScrollToBottomRef}
       >
-        {groupedMessages.map((message) => (
+        {groupedMessages.map((messages) => (
           <GroupMessage
             user={user}
-            key={message.id}
-            comment={message}
+            key={`group ${messages[0].id}`}
+            comments={messages}
             group={group}
             onReplyClick={onReplyClick}
-            highlight={message.id === scrollToMessageId}
+            highlight={messages[0].id === scrollToMessageId}
             setRef={
-              scrollToMessageId === message.id
+              scrollToMessageId === messages[0].id
                 ? setScrollToMessageRef
                 : undefined
             }
-            tips={tips[message.id] ?? {}}
+            tips={tips[messages[0].id] ?? {}}
           />
         ))}
         {messages.length === 0 && (
@@ -140,7 +144,7 @@ export function GroupChat(props: {
             No messages yet. Why not{isMember ? ` ` : ' join and '}
             <button
               className={'cursor-pointer font-bold text-gray-700'}
-              onClick={() => focusInput()}
+              onClick={focusInput}
             >
               add one?
             </button>
@@ -158,15 +162,12 @@ export function GroupChat(props: {
           </div>
           <div className={'flex-1'}>
             <CommentInputTextArea
-              commentText={messageText}
-              setComment={setMessageText}
-              isReply={false}
+              editor={editor}
+              upload={upload}
               user={user}
               replyToUsername={replyToUsername}
               submitComment={submitMessage}
               isSubmitting={isSubmitting}
-              enterToSubmitOnDesktop={true}
-              setRef={setInputRef}
             />
           </div>
         </div>
@@ -177,16 +178,18 @@ export function GroupChat(props: {
 
 const GroupMessage = memo(function GroupMessage_(props: {
   user: User | null | undefined
-  comment: Comment
+  comments: Comment[]
   group: Group
   onReplyClick?: (comment: Comment) => void
   setRef?: (ref: HTMLDivElement) => void
   highlight?: boolean
   tips: CommentTips
 }) {
-  const { comment, onReplyClick, group, setRef, highlight, user, tips } = props
-  const { text, userUsername, userName, userAvatarUrl, createdTime } = comment
-  const isCreatorsComment = user && comment.userId === user.id
+  const { comments, onReplyClick, group, setRef, highlight, user, tips } = props
+  const first = comments[0]
+  const { id, userUsername, userName, userAvatarUrl, createdTime } = first
+
+  const isCreatorsComment = user && comments[0].userId === user.id
   return (
     <Col
       ref={setRef}
@@ -216,15 +219,17 @@ const GroupMessage = memo(function GroupMessage_(props: {
           prefix={'group'}
           slug={group.slug}
           createdTime={createdTime}
-          elementId={comment.id}
+          elementId={id}
         />
       </Row>
       <Row className={'text-black'}>
-        <TruncatedComment
-          comment={text}
-          moreHref={groupPath(group.slug)}
-          shouldTruncate={false}
-        />
+        {comments.map((comment) => (
+          <TruncatedComment
+            comment={comment.content} // TODO: || comment.text
+            moreHref={groupPath(group.slug)}
+            shouldTruncate={false}
+          />
+        ))}
       </Row>
       <Row>
         {!isCreatorsComment && onReplyClick && (
@@ -232,7 +237,7 @@ const GroupMessage = memo(function GroupMessage_(props: {
             className={
               'self-start py-1 text-xs font-bold text-gray-500 hover:underline'
             }
-            onClick={() => onReplyClick(comment)}
+            onClick={() => onReplyClick(first)}
           >
             Reply
           </button>
@@ -242,7 +247,7 @@ const GroupMessage = memo(function GroupMessage_(props: {
             {formatMoney(sum(Object.values(tips)))}
           </span>
         )}
-        {!isCreatorsComment && <Tipper comment={comment} tips={tips} />}
+        {!isCreatorsComment && <Tipper comment={first} tips={tips} />}
       </Row>
     </Col>
   )
diff --git a/web/lib/firebase/comments.ts b/web/lib/firebase/comments.ts
index 3093f764..e0c7743b 100644
--- a/web/lib/firebase/comments.ts
+++ b/web/lib/firebase/comments.ts
@@ -14,6 +14,7 @@ import { User } from 'common/user'
 import { Comment } from 'common/comment'
 import { removeUndefinedProps } from 'common/util/object'
 import { track } from '@amplitude/analytics-browser'
+import { JSONContent } from '@tiptap/react'
 
 export type { Comment }
 
@@ -21,7 +22,7 @@ export const MAX_COMMENT_LENGTH = 10000
 
 export async function createCommentOnContract(
   contractId: string,
-  text: string,
+  content: JSONContent,
   commenter: User,
   betId?: string,
   answerOutcome?: string,
@@ -34,7 +35,7 @@ export async function createCommentOnContract(
     id: ref.id,
     contractId,
     userId: commenter.id,
-    text: text.slice(0, MAX_COMMENT_LENGTH),
+    content: content,
     createdTime: Date.now(),
     userName: commenter.name,
     userUsername: commenter.username,
@@ -53,7 +54,7 @@ export async function createCommentOnContract(
 }
 export async function createCommentOnGroup(
   groupId: string,
-  text: string,
+  content: JSONContent,
   user: User,
   replyToCommentId?: string
 ) {
@@ -62,7 +63,7 @@ export async function createCommentOnGroup(
     id: ref.id,
     groupId,
     userId: user.id,
-    text: text.slice(0, MAX_COMMENT_LENGTH),
+    content: content,
     createdTime: Date.now(),
     userName: user.name,
     userUsername: user.username,