diff --git a/lib/completions/prompt_messages_builder.rb b/lib/completions/prompt_messages_builder.rb
index 840fecf1..aa753c7c 100644
--- a/lib/completions/prompt_messages_builder.rb
+++ b/lib/completions/prompt_messages_builder.rb
@@ -6,7 +6,6 @@ module DiscourseAi
       MAX_CHAT_UPLOADS = 5
       MAX_TOPIC_UPLOADS = 5
       attr_reader :chat_context_posts
-      attr_reader :chat_context_post_upload_ids
       attr_accessor :topic
 
       def self.messages_from_chat(
@@ -113,12 +112,13 @@ module DiscourseAi
                   FROM upload_references ref
                   WHERE ref.target_type = 'Post' AND ref.target_id = posts.id
                ) as upload_ids",
+              "posts.created_at",
             )
 
         builder = new
         builder.topic = post.topic
 
-        context.reverse_each do |raw, username, custom_prompt, upload_ids|
+        context.reverse_each do |raw, username, custom_prompt, upload_ids, created_at|
           custom_prompt_translation =
             Proc.new do |message|
               # We can't keep backwards-compatibility for stored functions.
@@ -134,6 +134,7 @@ module DiscourseAi
 
                 thinking = message[4]
                 custom_context[:thinking] = thinking if thinking
+                custom_context[:created_at] = created_at
 
                 builder.push(**custom_context)
               end
@@ -149,6 +150,7 @@ module DiscourseAi
             if upload_ids.present? && context[:type] == :user && include_uploads
               context[:upload_ids] = upload_ids.compact
             end
+            context[:created_at] = created_at
 
             builder.push(**context)
           end
@@ -159,6 +161,7 @@ module DiscourseAi
 
       def initialize
         @raw_messages = []
+        @timestamps = {}
       end
 
       def set_chat_context_posts(post_ids, guardian, include_uploads:)
@@ -171,27 +174,66 @@ module DiscourseAi
             posts << post
           end
         if posts.present?
-          posts_context =
-            +"\nThis chat is in the context of the Discourse topic '#{posts[0].topic.title}':\n\n"
-          posts_context = +"{{{\n"
+          posts_context = []
+          posts_context << "\nThis chat is in the context of the Discourse topic '#{posts[0].topic.title}':\n\n"
+          posts_context << "{{{\n"
           posts.each do |post|
             posts_context << "url: #{post.url}\n"
             posts_context << "#{post.username}: #{post.raw}\n\n"
+            if include_uploads
+              post.uploads.each { |upload| posts_context << { upload_id: upload.id } }
+            end
           end
           posts_context << "}}}"
           @chat_context_posts = posts_context
-          if include_uploads
-            uploads = []
-            posts.each { |post| uploads.concat(post.uploads.pluck(:id)) }
-            uploads.uniq!
-            @chat_context_post_upload_ids = uploads.take(MAX_CHAT_UPLOADS)
-          end
         end
       end
 
       def to_a(limit: nil, style: nil)
+        # topic and chat array are special, they are single messages that contain all history
         return chat_array(limit: limit) if style == :chat
         return topic_array if style == :topic
+
+        # the rest of the styles can include multiple messages
+        result = valid_messages_array(@raw_messages)
+        prepend_chat_post_context(result) if style == :chat_with_context
+
+        if limit
+          result[0..limit]
+        else
+          result
+        end
+      end
+
+      def push(type:, content:, name: nil, upload_ids: nil, id: nil, thinking: nil, created_at: nil)
+        if !%i[user model tool tool_call system].include?(type)
+          raise ArgumentError, "type must be either :user, :model, :tool, :tool_call or :system"
+        end
+        raise ArgumentError, "upload_ids must be an array" if upload_ids && !upload_ids.is_a?(Array)
+
+        content = [content, *upload_ids.map { |upload_id| { upload_id: upload_id } }] if upload_ids
+        message = { type: type, content: content }
+        message[:name] = name.to_s if name
+        message[:id] = id.to_s if id
+        if thinking
+          message[:thinking] = thinking["thinking"] if thinking["thinking"]
+          message[:thinking_signature] = thinking["thinking_signature"] if thinking[
+            "thinking_signature"
+          ]
+          message[:redacted_thinking_signature] = thinking[
+            "redacted_thinking_signature"
+          ] if thinking["redacted_thinking_signature"]
+        end
+
+        @raw_messages << message
+        @timestamps[message] = created_at if created_at
+
+        message
+      end
+
+      private
+
+      def valid_messages_array(messages)
         result = []
 
         # this will create a "valid" messages array
@@ -199,7 +241,7 @@ module DiscourseAi
         # 2. ensures we always end with a user message
         # 3. ensures we always interleave user and model messages
         last_type = nil
-        @raw_messages.each do |message|
+        messages.each do |message|
           next if !last_type && message[:type] != :user
 
           if last_type == :tool_call && message[:type] != :tool
@@ -239,52 +281,27 @@ module DiscourseAi
           last_type = message[:type]
         end
 
-        if style == :chat_with_context && @chat_context_posts
-          buffer = +"You are replying inside a Discourse chat."
-          buffer << "\n"
-          buffer << @chat_context_posts
-          buffer << "\n"
-          buffer << "Your instructions are:\n"
-          result[0][:content] = "#{buffer}#{result[0][:content]}"
-          if @chat_context_post_upload_ids.present?
-            result[0][:upload_ids] = (result[0][:upload_ids] || []).concat(
-              @chat_context_post_upload_ids,
-            )
-          end
-        end
-
-        if limit
-          result[0..limit]
-        else
-          result
-        end
+        result
       end
 
-      def push(type:, content:, name: nil, upload_ids: nil, id: nil, thinking: nil)
-        if !%i[user model tool tool_call system].include?(type)
-          raise ArgumentError, "type must be either :user, :model, :tool, :tool_call or :system"
-        end
-        raise ArgumentError, "upload_ids must be an array" if upload_ids && !upload_ids.is_a?(Array)
+      def prepend_chat_post_context(messages)
+        return if @chat_context_posts.blank?
 
-        content = [content, *upload_ids.map { |upload_id| { upload_id: upload_id } }] if upload_ids
-        message = { type: type, content: content }
-        message[:name] = name.to_s if name
-        message[:id] = id.to_s if id
-        if thinking
-          message[:thinking] = thinking["thinking"] if thinking["thinking"]
-          message[:thinking_signature] = thinking["thinking_signature"] if thinking[
-            "thinking_signature"
-          ]
-          message[:redacted_thinking_signature] = thinking[
-            "redacted_thinking_signature"
-          ] if thinking["redacted_thinking_signature"]
-        end
+        old_content = messages[0][:content]
+        old_content = [old_content] if !old_content.is_a?(Array)
 
-        @raw_messages << message
+        new_content = []
+        new_content << "You are replying inside a Discourse chat.\n"
+        new_content.concat(@chat_context_posts)
+        new_content << "\n"
+        new_content << "Your instructions are:\n"
+        new_content.concat(old_content)
+
+        compressed = compress_messages_buffer(new_content.flatten, max_uploads: MAX_CHAT_UPLOADS)
+
+        messages[0][:content] = compressed
       end
 
-      private
-
       def format_user_info(user)
         info = []
         info << user_role(user)
@@ -294,6 +311,34 @@ module DiscourseAi
         "#{user.username} (#{user.name}): #{info.compact.join(", ")}"
       end
 
+      def format_timestamp(timestamp)
+        return nil unless timestamp
+
+        time_diff = Time.now - timestamp
+
+        if time_diff < 1.minute
+          "just now"
+        elsif time_diff < 1.hour
+          mins = (time_diff / 1.minute).round
+          "#{mins} #{mins == 1 ? "minute" : "minutes"} ago"
+        elsif time_diff < 1.day
+          hours = (time_diff / 1.hour).round
+          "#{hours} #{hours == 1 ? "hour" : "hours"} ago"
+        elsif time_diff < 7.days
+          days = (time_diff / 1.day).round
+          "#{days} #{days == 1 ? "day" : "days"} ago"
+        elsif time_diff < 30.days
+          weeks = (time_diff / 7.days).round
+          "#{weeks} #{weeks == 1 ? "week" : "weeks"} ago"
+        elsif time_diff < 365.days
+          months = (time_diff / 30.days).round
+          "#{months} #{months == 1 ? "month" : "months"} ago"
+        else
+          years = (time_diff / 365.days).round
+          "#{years} #{years == 1 ? "year" : "years"} ago"
+        end
+      end
+
       def user_role(user)
         return "moderator" if user.moderator?
         return "admin" if user.admin?
@@ -323,45 +368,57 @@ module DiscourseAi
         end
       end
 
+      def format_topic_info(topic)
+        content_array = []
+
+        if topic.private_message?
+          content_array << "Private message info.\n"
+        else
+          content_array << "Topic information:\n"
+        end
+
+        content_array << "- URL: #{topic.url}\n"
+        content_array << "- Title: #{topic.title}\n"
+        if SiteSetting.tagging_enabled
+          tags = topic.tags.pluck(:name)
+          tags -= DiscourseTagging.hidden_tag_names if tags.present?
+          content_array << "- Tags: #{tags.join(", ")}\n" if tags.present?
+        end
+        if !topic.private_message?
+          content_array << "- Category: #{topic.category.name}\n" if topic.category
+        end
+        content_array << "- Number of replies: #{topic.posts_count - 1}\n\n"
+
+        content_array.join
+      end
+
+      def format_user_infos(usernames)
+        content_array = []
+
+        if usernames.present?
+          users_details =
+            User
+              .where(username: usernames)
+              .includes(:user_stat)
+              .map { |user| format_user_info(user) }
+              .compact
+          content_array << "User information:\n"
+          content_array << "- #{users_details.join("\n- ")}\n\n" if users_details.present?
+        end
+        content_array.join
+      end
+
       def topic_array
         raw_messages = @raw_messages.dup
         content_array = []
         content_array << "You are operating in a Discourse forum.\n\n"
-
-        if @topic
-          if @topic.private_message?
-            content_array << "Private message info.\n"
-          else
-            content_array << "Topic information:\n"
-          end
-
-          content_array << "- URL: #{@topic.url}\n"
-          content_array << "- Title: #{@topic.title}\n"
-          if SiteSetting.tagging_enabled
-            tags = @topic.tags.pluck(:name)
-            tags -= DiscourseTagging.hidden_tag_names if tags.present?
-            content_array << "- Tags: #{tags.join(", ")}\n" if tags.present?
-          end
-          if !@topic.private_message?
-            content_array << "- Category: #{@topic.category.name}\n" if @topic.category
-          end
-          content_array << "- Number of replies: #{@topic.posts_count - 1}\n\n"
-        end
+        content_array << format_topic_info(@topic) if @topic
 
         if raw_messages.present?
           usernames =
             raw_messages.filter { |message| message[:type] == :user }.map { |message| message[:id] }
 
-          if usernames.present?
-            users_details =
-              User
-                .where(username: usernames)
-                .includes(:user_stat)
-                .map { |user| format_user_info(user) }
-                .compact
-            content_array << "User information:\n"
-            content_array << "- #{users_details.join("\n- ")}\n\n" if users_details.present?
-          end
+          content_array << format_user_infos(usernames) if usernames.present?
         end
 
         last_user_message = raw_messages.pop
@@ -370,6 +427,8 @@ module DiscourseAi
           content_array << "Here is the conversation so far:\n"
           raw_messages.each do |message|
             content_array << "#{message[:id] || "User"}: "
+            timestamp = @timestamps[message]
+            content_array << "(#{format_timestamp(timestamp)}) " if timestamp
             content_array << message[:content]
             content_array << "\n\n"
           end
diff --git a/spec/lib/completions/prompt_messages_builder_spec.rb b/spec/lib/completions/prompt_messages_builder_spec.rb
index d2bb2a21..b8e1d7c0 100644
--- a/spec/lib/completions/prompt_messages_builder_spec.rb
+++ b/spec/lib/completions/prompt_messages_builder_spec.rb
@@ -95,6 +95,72 @@ describe DiscourseAi::Completions::PromptMessagesBuilder do
     expect(content).to include("How do I solve this")
   end
 
+  describe "chat context posts in direct messages" do
+    fab!(:dm_channel) { Fabricate(:direct_message_channel, users: [user, bot_user]) }
+    fab!(:dm_message) do
+      Fabricate(
+        :chat_message,
+        chat_channel: dm_channel,
+        user: user,
+        message: "I have a question about the topic",
+      )
+    end
+
+    fab!(:topic) { Fabricate(:topic, title: "Important topic for context") }
+    fab!(:post1) { Fabricate(:post, topic: topic, user: other_user, raw: "This is the first post") }
+    fab!(:post2) { Fabricate(:post, topic: topic, user: user, raw: "And here's a follow-up") }
+
+    it "correctly includes topic posts as context in direct message channels" do
+      context =
+        described_class.messages_from_chat(
+          dm_message,
+          channel: dm_channel,
+          context_post_ids: [post1.id, post2.id],
+          max_messages: 10,
+          include_uploads: false,
+          bot_user_ids: [bot_user.id],
+          instruction_message: nil,
+        )
+
+      expect(context.length).to eq(1)
+      content = context.first[:content]
+
+      # First part should contain the context intro
+      expect(content).to include("You are replying inside a Discourse chat")
+      expect(content).to include(
+        "This chat is in the context of the Discourse topic 'Important topic for context'",
+      )
+      expect(content).to include(post1.username)
+      expect(content).to include("This is the first post")
+      expect(content).to include(post2.username)
+      expect(content).to include("And here's a follow-up")
+
+      # Last part should have the user's message
+      expect(content).to include("I have a question about the topic")
+    end
+
+    it "includes uploads from context posts when include_uploads is true" do
+      upload = Fabricate(:upload, user: user)
+      UploadReference.create!(target: post1, upload: upload)
+
+      context =
+        described_class.messages_from_chat(
+          dm_message,
+          channel: dm_channel,
+          context_post_ids: [post1.id],
+          max_messages: 10,
+          include_uploads: true,
+          bot_user_ids: [bot_user.id],
+          instruction_message: nil,
+        )
+
+      # Verify the upload reference is included
+      upload_hashes = context.first[:content].select { |item| item.is_a?(Hash) && item[:upload_id] }
+      expect(upload_hashes).to be_present
+      expect(upload_hashes.first[:upload_id]).to eq(upload.id)
+    end
+  end
+
   describe ".messages_from_chat" do
     fab!(:dm_channel) { Fabricate(:direct_message_channel, users: [user, bot_user]) }
     fab!(:dm_message1) do
@@ -366,7 +432,9 @@ describe DiscourseAi::Completions::PromptMessagesBuilder do
       # will be brittle, but open to changing this
     end
 
-    it "handles uploads correctly in topic style messages" do
+    it "handles uploads correctly in topic style messages (and times)" do
+      freeze_time 1.month.ago
+
       # Use Discourse's upload format in the post raw content
       upload_markdown = "![test|658x372](#{image_upload1.short_url})"
 
@@ -382,6 +450,8 @@ describe DiscourseAi::Completions::PromptMessagesBuilder do
 
       upload2_markdown = "![test|658x372](#{image_upload2.short_url})"
 
+      freeze_time 1.month.from_now
+
       post2_with_upload =
         Fabricate(
           :post,
@@ -415,6 +485,7 @@ describe DiscourseAi::Completions::PromptMessagesBuilder do
       # second image
       expect(content.length).to eq(4)
       expect(content[0]).to include("This is the original")
+      expect(content[0]).to include("(1 month ago)")
       expect(content[1]).to eq({ upload_id: image_upload1.id })
       expect(content[2]).to include("different image")
       expect(content[3]).to eq({ upload_id: image_upload2.id })