diff --git a/internal/webserver/handler_messages.go b/internal/webserver/handler_messages.go
index 1ae85f5..4211b76 100644
--- a/internal/webserver/handler_messages.go
+++ b/internal/webserver/handler_messages.go
@@ -57,10 +57,18 @@ func (app *Application) message_detail(w http.ResponseWriter, r *http.Request) {
 	if r.URL.Query().Get("scroll_bottom") != "0" {
 		chat_view_data.ScrollBottom = true
 	}
-	chat_contents := app.Profile.GetChatRoomContents(room_id, chat_view_data.LatestPollingTimestamp)
-	chat_view_data.MergeWith(chat_contents.DMTrove)
+
+	c := persistence.NewConversationCursor(room_id)
+	c.SinceTimestamp = scraper.TimestampFromUnixMilli(int64(chat_view_data.LatestPollingTimestamp))
+	if cursor_value := r.URL.Query().Get("cursor"); cursor_value != "" {
+		until_time, err := strconv.Atoi(cursor_value)
+		panic_if(err) // TODO: 400 not 500
+		c.UntilTimestamp = scraper.TimestampFromUnixMilli(int64(until_time))
+	}
+	chat_contents := app.Profile.GetChatRoomMessagesByCursor(c)
 	chat_view_data.DMChatView.MergeWith(chat_contents.DMTrove)
 	chat_view_data.MessageIDs = chat_contents.MessageIDs
+	chat_view_data.Cursor = chat_contents.Cursor
 	if len(chat_view_data.MessageIDs) > 0 {
 		last_message_id := chat_view_data.MessageIDs[len(chat_view_data.MessageIDs)-1]
 		chat_view_data.LatestPollingTimestamp = int(chat_view_data.Messages[last_message_id].SentAt.UnixMilli())
@@ -72,6 +80,12 @@ func (app *Application) message_detail(w http.ResponseWriter, r *http.Request) {
 			app.buffered_render_htmx(w, "messages-with-poller", global_data, chat_view_data)
 			return
 		}
+
+		// Scrolling-back should add new messages to the top of the page
+		if r.URL.Query().Has("cursor") {
+			app.buffered_render_htmx(w, "messages-top", global_data, chat_view_data)
+			return
+		}
 	}
 
 	app.buffered_render_page(w, "tpl/messages.tpl", global_data, chat_view_data)
diff --git a/internal/webserver/server_test.go b/internal/webserver/server_test.go
index ec573b3..674425d 100644
--- a/internal/webserver/server_test.go
+++ b/internal/webserver/server_test.go
@@ -821,3 +821,24 @@ func TestMessagesRoomPollForUpdatesEmptyResult(t *testing.T) {
 		Val: "/messages/1488963321701171204-1178839081222115328?poll&latest_timestamp=1686025129144&scroll_bottom=1",
 	})
 }
+
+// Scroll back in the messages
+func TestMessagesPaginate(t *testing.T) {
+	assert := assert.New(t)
+	require := require.New(t)
+
+	// Boilerplate for setting an active user
+	app := webserver.NewApp(profile)
+	app.IsScrapingDisabled = true
+	app.ActiveUser = scraper.User{ID: 1488963321701171204, Handle: "Offline_Twatter"} // Simulate a login
+
+	// Chat detail
+	recorder := httptest.NewRecorder()
+	req := httptest.NewRequest("GET", "/messages/1488963321701171204-1178839081222115328?cursor=1686025129142", nil)
+	req.Header.Set("HX-Request", "true")
+	app.ServeHTTP(recorder, req)
+	resp := recorder.Result()
+	root, err := html.Parse(resp.Body)
+	require.NoError(err)
+	assert.Len(cascadia.QueryAll(root, selector(".dm-message")), 2)
+}
diff --git a/internal/webserver/tpl/tweet_page_includes/chat_view.tpl b/internal/webserver/tpl/tweet_page_includes/chat_view.tpl
index 04041c1..939a22c 100644
--- a/internal/webserver/tpl/tweet_page_includes/chat_view.tpl
+++ b/internal/webserver/tpl/tweet_page_includes/chat_view.tpl
@@ -106,6 +106,7 @@
     {{end}}
     <div class="chat-messages">
       {{if .ActiveRoomID}}
+        {{template "conversation-top" .}}
         {{template "messages-with-poller" .}}
       {{end}}
     </div>
@@ -190,3 +191,24 @@
     {{end}}
   ></span>
 {{end}}
+
+{{define "conversation-top"}}
+  <div class="conversation-top">
+    {{if .Cursor.CursorPosition.IsEnd}}
+      <!-- TODO: make a reusable eof-indicator -->
+      <div class="eof-indicator">Beginning of conversation</div>
+    {{else}}
+      <a class="show-more-button button"
+        hx-get="?cursor={{.Cursor.CursorValue}}" {{/* TODO: this might require a `cursor_to_query_params` if the same view is used for searching */}}
+        hx-target=".conversation-top"
+        hx-swap="outerHTML"
+      >Show more</a>
+    {{end}}
+  </div>
+{{end}}
+
+{{/* convenience template for htmx requests */}}
+{{define "messages-top"}}
+  {{template "conversation-top" .}}
+  {{template "messages" .}}
+{{end}}
diff --git a/pkg/persistence/dm_queries.go b/pkg/persistence/dm_queries.go
index 45a8073..bc2094e 100644
--- a/pkg/persistence/dm_queries.go
+++ b/pkg/persistence/dm_queries.go
@@ -264,9 +264,14 @@ func (p Profile) GetChatRoomsPreview(id UserID) DMChatView {
 }
 
 // Get chat room detail, including participants and messages
+// TODO: get rid of this function (behavior has been moved to GetChatRoomMessagesByCursor)
 func (p Profile) GetChatRoomContents(id DMChatRoomID, latest_timestamp int) DMChatView {
 	c := NewConversationCursor(id)
 	c.SinceTimestamp = TimestampFromUnixMilli(int64(latest_timestamp))
+	return p.GetChatRoomMessagesByCursor(c)
+}
+
+func (p Profile) GetChatRoomMessagesByCursor(c DMCursor) DMChatView {
 	ret := p.NextDMPage(c)
 
 	var room DMChatRoom
@@ -274,7 +279,7 @@ func (p Profile) GetChatRoomContents(id DMChatRoomID, latest_timestamp int) DMCh
 		select `+CHAT_ROOMS_ALL_SQL_FIELDS+`
 		  from chat_rooms
 		 where id = ?
-	`, id)
+	`, c.ConversationId)
 	if err != nil {
 		panic(err)
 	}