Fix pp of an Array of messages

CHANGELOG.md

@@ -5,6 +5,12 @@ All notable changes to this project will be documented in this file.
 The format is based on [Keep a Changelog](https://keepachangelog.com/en/1.0.0/),
 and this project adheres to [Semantic Versioning](https://semver.org/spec/v2.0.0.html).
 
+## [0.8.1] - 2026-10-19
+
+### Fixed
+
+- **`pp` of an Array of messages**: `pp chat.messages` (and IRB's echo of `chat.messages`) printed `},{` and `}{` between messages and piled the leftover separators up before the closing bracket (`} , ]`). Messages now print as `[{...}, {...}]`, matching `p`. `AI::Items` had the same problem inside an Array and gets the same fix.
+
 ## [0.8.0] - 2026-10-19
 
 ### Changed

Gemfile.lock

@@ -1,7 +1,7 @@
 PATH
   remote: .
   specs:
-    ai-chat (0.8.0)
+    ai-chat (0.8.1)
       amazing_print (~> 2.0)
       base64 (~> 0.1, > 0.1.1)
       json (~> 2.0)

ai-chat.gemspec

@@ -2,7 +2,7 @@
 
 Gem::Specification.new do |spec|
   spec.name = "ai-chat"
-  spec.version = "0.8.0"
+  spec.version = "0.8.1"
   spec.authors = ["Raghu Betina", "Jelani Woods"]
   spec.email = ["[email protected]", "[email protected]"]
   spec.homepage = "https://github.com/firstdraft/ai-chat"

lib/ai/items.rb

@@ -35,7 +35,9 @@ def pretty_inspect
       "#{inspect}\n"
     end
 
+    # Same direct write as AI::Message#pretty_print, for the same reasons.
     def pretty_print(q)
+      q.flush
       q.output << inspect
     end
 

lib/ai/message.rb

@@ -11,8 +11,11 @@ def pretty_inspect
     end
 
     # IRB's ColorPrinter calls pretty_print and re-colorizes text,
-    # which escapes our ANSI codes. Write directly to output to bypass.
+    # which escapes our ANSI codes. Write directly to output to bypass,
+    # but flush first: inside an Array, PP is still buffering the "[" and
+    # earlier separators, so an unflushed write lands ahead of them.
     def pretty_print(q)
+      q.flush
       q.output << inspect
     end
 

spec/unit/chat_spec.rb

@@ -743,6 +743,51 @@ def schema_client_double
     it "returns a String" do
       expect(chat.inspect).to be_a(String)
     end
+
+    # Lessons show this output verbatim, so pin the exact layout.
+    context "when not writing to a terminal" do
+      before { allow($stdout).to receive(:tty?).and_return(false) }
+
+      it "lists a new chat's attributes one per line" do
+        new_chat = AI::Chat.new(api_key: "test-key", proxy: false)
+
+        expect(new_chat.inspect).to eq(<<~TEXT.chomp)
+          #<AI::Chat
+            @model: "gpt-6-luna"
+            @reasoning_effort: "low"
+            @conversation_id: nil
+            @messages: []
+            @verbosity: :medium
+          >
+        TEXT
+      end
+
+      it "lists messages by index with aligned keys" do
+        proxied_chat = AI::Chat.new(api_key: "test-key", proxy: true)
+        proxied_chat.system("You are an assistant that talks like Shakespeare.")
+        proxied_chat.user("What is the motto of Ruby lang?")
+
+        expect(proxied_chat.inspect).to eq(<<~TEXT.chomp)
+          #<AI::Chat
+            @model: "gpt-6-luna"
+            @reasoning_effort: "low"
+            @conversation_id: nil
+            @messages: [
+              [0] {
+                     role: "system",
+                  content: "You are an assistant that talks like Shakespeare."
+              },
+              [1] {
+                     role: "user",
+                  content: "What is the motto of Ruby lang?"
+              }
+          ]
+            @proxy: true
+            @verbosity: :medium
+          >
+        TEXT
+      end
+    end
   end
 
   describe "#pretty_inspect" do

spec/unit/items_spec.rb

@@ -61,6 +61,12 @@
       expect(out).to include("Conversation: conv_abc123")
       expect(out).to include("Items: 2")
     end
+
+    it "keeps separators in place inside an Array" do
+      out = PP.pp([items, items], +"")
+
+      expect(out).to eq("[#{items.inspect}, #{items.inspect}]\n")
+    end
   end
 
   describe "#to_html" do

spec/unit/message_spec.rb

@@ -68,11 +68,35 @@
     end
   end
 
+  describe "printing an Array of messages with pp" do
+    before { allow($stdout).to receive(:tty?).and_return(false) }
+
+    it "keeps each separator between the messages it separates" do
+      messages = [
+        AI::Message[role: "user", content: "Hello"],
+        AI::Message[role: "assistant", content: "Hi!", response: {id: "resp_1"}]
+      ]
+
+      expect(PP.pp(messages, +"")).to eq(<<~TEXT)
+        [{
+               role: "user",
+            content: "Hello"
+        }, {
+                role: "assistant",
+             content: "Hi!",
+            response: {
+                id: "resp_1"
+            }
+        }]
+      TEXT
+    end
+  end
+
   describe "#pretty_print" do
     it "writes directly to output to bypass IRB colorization" do
       message = AI::Message[role: "user", content: "Hello"]
       output = StringIO.new
-      mock_q = double("PrettyPrint", output: output)
+      mock_q = double("PrettyPrint", output: output, flush: nil)
 
       message.pretty_print(mock_q)