diff --git a/lib/completions/dialects/chat_gpt.rb b/lib/completions/dialects/chat_gpt.rb
index d3d1030b..4d511a0b 100644
--- a/lib/completions/dialects/chat_gpt.rb
+++ b/lib/completions/dialects/chat_gpt.rb
@@ -21,6 +21,8 @@ module DiscourseAi
           end
         end
 
+        VALID_ID_REGEX = /\A[a-zA-Z0-9_]+\z/
+
         def translate
           messages = prompt.messages
 
@@ -32,6 +34,11 @@ module DiscourseAi
 
           trimmed_messages = trim_messages(messages)
 
+          embed_user_ids =
+            trimmed_messages.any? do |m|
+              m[:id] && m[:type] == :user && !m[:id].to_s.match?(VALID_ID_REGEX)
+            end
+
           trimmed_messages.map do |msg|
             if msg[:type] == :system
               { role: "system", content: msg[:content] }
@@ -49,9 +56,15 @@ module DiscourseAi
             elsif msg[:type] == :tool
               { role: "tool", tool_call_id: msg[:id], content: msg[:content] }
             else
-              { role: "user", content: msg[:content] }.tap do |user_msg|
-                user_msg[:name] = msg[:id] if msg[:id]
+              user_message = { role: "user", content: msg[:content] }
+              if msg[:id]
+                if embed_user_ids
+                  user_message[:content] = "#{msg[:id]}: #{msg[:content]}"
+                else
+                  user_message[:name] = msg[:id]
+                end
               end
+              user_message
             end
           end
         end
@@ -109,6 +122,10 @@ module DiscourseAi
             8192
           when "gpt-4-32k"
             32_768
+          when "gpt-4-1106-preview"
+            131_072
+          when "gpt-4-turbo"
+            131_072
           else
             8192
           end
diff --git a/lib/completions/dialects/claude.rb b/lib/completions/dialects/claude.rb
index acb0f538..f05739c0 100644
--- a/lib/completions/dialects/claude.rb
+++ b/lib/completions/dialects/claude.rb
@@ -29,7 +29,7 @@ module DiscourseAi
               if msg[:type] == :system
                 memo << "Human: " unless uses_system_message?
                 memo << msg[:content]
-                if prompt.tools
+                if prompt.tools.present?
                   memo << "\n"
                   memo << build_tools_prompt
                 end
@@ -49,7 +49,9 @@ module DiscourseAi
                 </function_results>
                 TEXT
               else
-                memo << "\n\nHuman: #{msg[:content]}"
+                memo << "\n\nHuman: "
+                memo << "#{msg[:id]}: " if msg[:id]
+                memo << msg[:content]
               end
 
               memo
diff --git a/lib/completions/dialects/dialect.rb b/lib/completions/dialects/dialect.rb
index 1d968746..8b6acd59 100644
--- a/lib/completions/dialects/dialect.rb
+++ b/lib/completions/dialects/dialect.rb
@@ -157,6 +157,8 @@ module DiscourseAi
             reversed_trimmed_msgs << dupped_msg
           end
 
+          reversed_trimmed_msgs.pop if reversed_trimmed_msgs.last&.dig(:type) == :tool
+
           trimmed_messages.concat(reversed_trimmed_msgs.reverse)
         end
 
diff --git a/lib/completions/prompt.rb b/lib/completions/prompt.rb
index e5a2e2e8..5819055f 100644
--- a/lib/completions/prompt.rb
+++ b/lib/completions/prompt.rb
@@ -22,10 +22,6 @@ module DiscourseAi
         @messages.concat(messages)
 
         @messages.each { |message| validate_message(message) }
-        @messages.each do |message|
-          message[:id] = clean_username(message[:id]) if message[:type] == :user &&
-            message[:id].present?
-        end
         @messages.each_cons(2) { |last_turn, new_turn| validate_turn(last_turn, new_turn) }
 
         @tools = tools
@@ -34,8 +30,7 @@ module DiscourseAi
       def push(type:, content:, id: nil)
         return if type == :system
         new_message = { type: type, content: content }
-
-        new_message[:id] = type == :user ? clean_username(id) : id if id && type != :model
+        new_message[:id] = id.to_s if id
 
         validate_message(new_message)
         validate_turn(messages.last, new_message)
@@ -45,16 +40,6 @@ module DiscourseAi
 
       private
 
-      def clean_username(username)
-        if username.match?(/\0[a-zA-Z0-9_-]{1,64}\z/)
-          username
-        else
-          # not the best in the world, but this is what we have to work with
-          # if sites enable unicode usernames this can get messy
-          username.gsub(/[^a-zA-Z0-9_-]/, "_")[0..63]
-        end
-      end
-
       def validate_message(message)
         valid_types = %i[system user model tool tool_call]
         if !valid_types.include?(message[:type])
diff --git a/spec/lib/completions/dialects/chat_gpt_spec.rb b/spec/lib/completions/dialects/chat_gpt_spec.rb
index d26c6fe1..c1714d75 100644
--- a/spec/lib/completions/dialects/chat_gpt_spec.rb
+++ b/spec/lib/completions/dialects/chat_gpt_spec.rb
@@ -18,6 +18,29 @@ RSpec.describe DiscourseAi::Completions::Dialects::ChatGpt do
       expect(translated).to contain_exactly(*open_ai_version)
     end
 
+    it "will retain usernames for unicode usernames, correctly in mixed mode" do
+      prompt =
+        DiscourseAi::Completions::Prompt.new(
+          "You are a bot",
+          messages: [
+            { id: "👻", type: :user, content: "Message1" },
+            { type: :model, content: "Ok" },
+            { id: "joe", type: :user, content: "Message2" },
+          ],
+        )
+
+      translated = context.dialect(prompt).translate
+
+      expect(translated).to eq(
+        [
+          { role: "system", content: "You are a bot" },
+          { role: "user", content: "👻: Message1" },
+          { role: "assistant", content: "Ok" },
+          { role: "user", content: "joe: Message2" },
+        ],
+      )
+    end
+
     it "translates tool_call and tool messages" do
       expect(context.multi_turn_scenario).to eq(
         [
diff --git a/spec/lib/completions/dialects/claude_spec.rb b/spec/lib/completions/dialects/claude_spec.rb
index 4e8b877a..5c4619f0 100644
--- a/spec/lib/completions/dialects/claude_spec.rb
+++ b/spec/lib/completions/dialects/claude_spec.rb
@@ -15,7 +15,7 @@ RSpec.describe DiscourseAi::Completions::Dialects::Claude do
       #{context.dialect_tools}</tools>
 
       Human: #{context.simple_user_input}
-      
+
       Assistant:
       TEXT
 
@@ -31,11 +31,11 @@ RSpec.describe DiscourseAi::Completions::Dialects::Claude do
       <tools>
       #{context.dialect_tools}</tools>
 
-      Human: This is a message by a user
+      Human: user1: This is a message by a user
 
       Assistant: I'm a previous bot reply, that's why there's no user
 
-      Human: This is a new message by a user
+      Human: user1: This is a new message by a user
 
       Assistant:
       <function_results>
@@ -46,7 +46,7 @@ RSpec.describe DiscourseAi::Completions::Dialects::Claude do
       </json>
       </result>
       </function_results>
-      
+
       Assistant:
       TEXT
 
@@ -60,5 +60,31 @@ RSpec.describe DiscourseAi::Completions::Dialects::Claude do
 
       expect(translated.length).to be < context.long_message_text(length: length).length
     end
+
+    it "retains usernames in generated prompt" do
+      prompt =
+        DiscourseAi::Completions::Prompt.new(
+          "You are a bot",
+          messages: [
+            { id: "👻", type: :user, content: "Message1" },
+            { type: :model, content: "Ok" },
+            { id: "joe", type: :user, content: "Message2" },
+          ],
+        )
+
+      translated = context.dialect(prompt).translate
+
+      expect(translated).to eq(<<~TEXT.strip)
+        You are a bot
+
+        Human: 👻: Message1
+
+        Assistant: Ok
+
+        Human: joe: Message2
+
+        Assistant:
+        TEXT
+    end
   end
 end
diff --git a/spec/lib/completions/dialects/dialect_spec.rb b/spec/lib/completions/dialects/dialect_spec.rb
new file mode 100644
index 00000000..c54d1838
--- /dev/null
+++ b/spec/lib/completions/dialects/dialect_spec.rb
@@ -0,0 +1,38 @@
+# frozen_string_literal: true
+
+class TestDialect < DiscourseAi::Completions::Dialects::Dialect
+  attr_accessor :max_prompt_tokens
+
+  def trim(messages)
+    trim_messages(messages)
+  end
+
+  def self.tokenizer
+    Class.new do
+      def self.size(str)
+        str.length
+      end
+    end
+  end
+end
+
+RSpec.describe DiscourseAi::Completions::Dialects::Dialect do
+  describe "#trim_messages" do
+    it "should trim tool messages if tool_calls are trimmed" do
+      prompt = DiscourseAi::Completions::Prompt.new("12345")
+      prompt.push(type: :user, content: "12345")
+      prompt.push(type: :tool_call, content: "12345", id: 1)
+      prompt.push(type: :tool, content: "12345", id: 1)
+      prompt.push(type: :user, content: "12345")
+
+      dialect = TestDialect.new(prompt, "test")
+      dialect.max_prompt_tokens = 15 # fits the user messages and the tool_call message
+
+      trimmed = dialect.trim(prompt.messages)
+
+      expect(trimmed).to eq(
+        [{ type: :system, content: "12345" }, { type: :user, content: "12345" }],
+      )
+    end
+  end
+end
diff --git a/spec/lib/completions/prompt_spec.rb b/spec/lib/completions/prompt_spec.rb
index 7ef4620e..2fa150e5 100644
--- a/spec/lib/completions/prompt_spec.rb
+++ b/spec/lib/completions/prompt_spec.rb
@@ -21,18 +21,6 @@ RSpec.describe DiscourseAi::Completions::Prompt do
       bad_messages3 = [{ content: "some content associated to no one" }]
       expect { described_class.new("a bot", messages: bad_messages3) }.to raise_error(ArgumentError)
     end
-
-    it "cleans unicode usernames" do
-      unicode_username = "罗马罗马"
-
-      prompt =
-        described_class.new(
-          "a bot",
-          messages: [{ type: :user, content: user_msg, id: unicode_username }],
-        )
-
-      expect(prompt.messages.last[:id]).to eq("____")
-    end
   end
 
   describe "#push" do
@@ -74,14 +62,5 @@ RSpec.describe DiscourseAi::Completions::Prompt do
       expect(system_message[:content]).to eq(user_msg)
       expect(system_message[:id]).to eq(username)
     end
-
-    it "cleans unicode usernames" do
-      unicode_username = "罗马罗马"
-      prompt.push(type: :user, content: user_msg, id: unicode_username)
-
-      user_message = prompt.messages.last
-
-      expect(user_message[:id]).to eq("____")
-    end
   end
 end