diff --git a/app/assets/javascripts/pretty-text/addon/engines/discourse-markdown-it.js b/app/assets/javascripts/pretty-text/addon/engines/discourse-markdown-it.js
index c806dc0ffde..84f8ce8c37a 100644
--- a/app/assets/javascripts/pretty-text/addon/engines/discourse-markdown-it.js
+++ b/app/assets/javascripts/pretty-text/addon/engines/discourse-markdown-it.js
@@ -423,6 +423,7 @@ function unhoistForCooked(hoisted, cooked) {
         found = true;
         return hoisted[key];
       });
+      delete hoisted[key];
     };
 
     while (found) {
@@ -578,14 +579,16 @@ export function setup(opts, siteSettings, state) {
 
 export function cook(raw, opts) {
   // we still have to hoist html_raw nodes so they bypass the allowlister
-  // this is the case for oneboxes
-  let hoisted = {};
-  opts.discourse.hoisted = hoisted;
+  // this is the case for oneboxes and also certain plugins that require
+  // raw HTML rendering within markdown bbcode rules
+  opts.discourse.hoisted ??= {};
 
   const rendered = opts.engine.render(raw);
   let cooked = opts.discourse.sanitizer(rendered).trim();
-  cooked = unhoistForCooked(hoisted, cooked);
-  delete opts.discourse.hoisted;
+
+  // opts.discourse.hoisted guid keys will be deleted within here to
+  // keep the object empty
+  cooked = unhoistForCooked(opts.discourse.hoisted, cooked);
 
   return cooked;
 }
diff --git a/plugins/chat/spec/integration/post_chat_quote_spec.rb b/plugins/chat/spec/integration/post_chat_quote_spec.rb
index 1c1e0430bd5..51d5c327cfe 100644
--- a/plugins/chat/spec/integration/post_chat_quote_spec.rb
+++ b/plugins/chat/spec/integration/post_chat_quote_spec.rb
@@ -211,4 +211,52 @@ martin</div>
   ensure
     InlineOneboxer.invalidate("https://en.wikipedia.org/wiki/Hyperlink")
   end
+
+  it "handles nested chat transcripts in posts" do
+    SiteSetting.external_system_avatars_enabled = false
+    freeze_time
+
+    channel = Fabricate(:chat_channel)
+    message1 = Fabricate(:chat_message, chat_channel: channel, user: post.user)
+    message2 = Fabricate(:chat_message, chat_channel: channel, user: post.user)
+    md = ChatTranscriptService.new(channel, message2.user, messages_or_ids: [message2.id]).generate_markdown
+    message1.update!(message: md)
+    md_for_post = ChatTranscriptService.new(channel, message1.user, messages_or_ids: [message1.id]).generate_markdown
+    post.update!(raw: md_for_post)
+    expect(post.cooked.chomp).to eq(<<~COOKED.chomp)
+<div class="chat-transcript" data-message-id="#{message1.id}" data-username="#{message1.user.username}" data-datetime="#{message1.created_at.iso8601}" data-channel-name="#{channel.name}" data-channel-id="#{channel.id}">
+<div class="chat-transcript-user">
+<div class="chat-transcript-user-avatar">
+<img loading="lazy" alt="" width="20" height="20" src="//test.localhost#{post.user.avatar_template.gsub("{size}", "40")}" class="avatar">
+</div>
+<div class="chat-transcript-username">
+#{message1.user.username}</div>
+<div class="chat-transcript-datetime">
+<a href="/chat/channel/#{channel.id}/-?messageId=#{message1.id}" title="#{message1.created_at.iso8601}"></a>
+</div>
+<a class="chat-transcript-channel" href="/chat/channel/#{channel.id}/-">
+##{channel.name}</a>
+</div>
+<div class="chat-transcript-messages">
+<div class="chat-transcript" data-message-id="#{message2.id}" data-username="#{message2.user.username}" data-datetime="#{message2.created_at.iso8601}" data-channel-name="#{channel.name}" data-channel-id="#{channel.id}">
+<div class="chat-transcript-user">
+<div class="chat-transcript-user-avatar">
+<img loading="lazy" alt="" width="20" height="20" src="//test.localhost#{post.user.avatar_template.gsub("{size}", "40")}" class="avatar">
+</div>
+<div class="chat-transcript-username">
+#{message2.user.username}</div>
+<div class="chat-transcript-datetime">
+<a href="/chat/channel/#{channel.id}/-?messageId=#{message2.id}" title="#{message1.created_at.iso8601}"></a>
+</div>
+<a class="chat-transcript-channel" href="/chat/channel/#{channel.id}/-">
+##{channel.name}</a>
+</div>
+<div class="chat-transcript-messages">
+<p>#{message2.message}</p>
+</div>
+</div>
+</div>
+</div>
+    COOKED
+  end
 end