fix: ensure system role is first in advised request messages

spring-ai-client-chat/src/main/java/org/springframework/ai/chat/client/advisor/api/AdvisedRequest.java

@@ -60,6 +60,7 @@
  * @author Christian Tzolov
  * @author Thomas Vitale
  * @author Ilayaperumal Gopinathan
+ * @author Alexandros Pappas
  * @since 1.0.0
  */
 public record AdvisedRequest(
@@ -147,18 +148,24 @@ public AdvisedRequest updateContext(Function<Map<String, Object>, Map<String, Ob
 	}
 
 	public Prompt toPrompt() {
-		var messages = new ArrayList<>(this.messages());
+		List<Message> promptMessages = new ArrayList<>();
 
+		// 1. Start with existing conversation messages, if present
+		if (!CollectionUtils.isEmpty(this.messages())) {
+			promptMessages.addAll(this.messages());
+		}
+
+		// 2. Process the new SystemMessage, if present
 		String processedSystemText = this.systemText();
 		if (StringUtils.hasText(processedSystemText)) {
 			if (!CollectionUtils.isEmpty(this.systemParams())) {
 				processedSystemText = new PromptTemplate(processedSystemText, this.systemParams()).render();
 			}
-			messages.add(new SystemMessage(processedSystemText));
+			promptMessages.add(new SystemMessage(processedSystemText));
 		}
 
+		// 3. Process the new UserMessage, if present
 		String formatParam = (String) this.adviseContext().get("formatParam");
-
 		var processedUserText = StringUtils.hasText(formatParam)
 				? this.userText() + System.lineSeparator() + "{spring_ai_soc_format}" : this.userText();
 
@@ -170,9 +177,10 @@ public Prompt toPrompt() {
 			if (!CollectionUtils.isEmpty(userParams)) {
 				processedUserText = new PromptTemplate(processedUserText, userParams).render();
 			}
-			messages.add(new UserMessage(processedUserText, this.media()));
+			promptMessages.add(new UserMessage(processedUserText, this.media()));
 		}
 
+		// 4. Configure function-calling options, if applicable
 		if (this.chatOptions() instanceof FunctionCallingOptions functionCallingOptions) {
 			if (!this.functionNames().isEmpty()) {
 				functionCallingOptions.setFunctions(new HashSet<>(this.functionNames()));
@@ -185,7 +193,7 @@ public Prompt toPrompt() {
 			}
 		}
 
-		return new Prompt(messages, this.chatOptions());
+		return new Prompt(promptMessages, this.chatOptions());
 	}
 
 	/**

spring-ai-integration-tests/src/test/java/org/springframework/ai/integration/tests/client/advisor/MessageChatMemoryAdvisorIT.java

@@ -0,0 +1,82 @@
+package org.springframework.ai.integration.tests.client.advisor;
+
+import org.junit.jupiter.api.Test;
+import org.junit.jupiter.api.condition.EnabledIfEnvironmentVariable;
+import org.springframework.ai.chat.client.ChatClient;
+import org.springframework.ai.chat.client.advisor.AbstractChatMemoryAdvisor;
+import org.springframework.ai.chat.client.advisor.MessageChatMemoryAdvisor;
+import org.springframework.ai.chat.memory.InMemoryChatMemory;
+import org.springframework.ai.chat.model.ChatResponse;
+import org.springframework.ai.openai.OpenAiChatModel;
+import org.springframework.beans.factory.annotation.Autowired;
+import org.springframework.boot.test.context.SpringBootTest;
+
+import static org.assertj.core.api.Assertions.assertThat;
+
+/**
+ * Integration tests for {@link MessageChatMemoryAdvisor}.
+ *
+ * @author Alexandros Pappas
+ */
+@SpringBootTest
+@EnabledIfEnvironmentVariable(named = "OPENAI_API_KEY", matches = ".*")
+class MessageChatMemoryAdvisorIT {
+
+	@Autowired
+	OpenAiChatModel openAiChatModel;
+
+	@Test
+	void chatMemoryStoresAndRecallsConversation() {
+		var chatMemory = new InMemoryChatMemory();
+		var conversationId = "test-conversation";
+
+		var memoryAdvisor = MessageChatMemoryAdvisor.builder(chatMemory).conversationId(conversationId).build();
+
+		var chatClient = ChatClient.builder(openAiChatModel).defaultAdvisors(memoryAdvisor).build();
+
+		// First interaction
+		ChatResponse response1 = chatClient.prompt().user("Hello, my name is John.").call().chatResponse();
+
+		assertThat(response1).isNotNull();
+		String assistantReply1 = response1.getResult().getOutput().getText();
+		System.out.println("Assistant reply 1: " + assistantReply1);
+
+		// Second interaction - Verify memory recall
+		ChatResponse response2 = chatClient.prompt().user("What is my name?").call().chatResponse();
+
+		assertThat(response2).isNotNull();
+		String assistantReply2 = response2.getResult().getOutput().getText();
+		System.out.println("Assistant reply 2: " + assistantReply2);
+
+		assertThat(assistantReply2.toLowerCase()).contains("john");
+	}
+
+	@Test
+	void separateConversationsDoNotMixMemory() {
+		var chatMemory = new InMemoryChatMemory();
+
+		var memoryAdvisor = MessageChatMemoryAdvisor.builder(chatMemory).build();
+
+		var chatClient = ChatClient.builder(openAiChatModel).defaultAdvisors(memoryAdvisor).build();
+
+		// First conversation
+		chatClient.prompt()
+			.user("Remember my secret code is blue.")
+			.advisors(advisors -> advisors.param(AbstractChatMemoryAdvisor.CHAT_MEMORY_CONVERSATION_ID_KEY, "conv-1"))
+			.call();
+
+		// Second conversation
+		ChatResponse response = chatClient.prompt()
+			.user("Do you remember my secret code?")
+			.advisors(advisors -> advisors.param(AbstractChatMemoryAdvisor.CHAT_MEMORY_CONVERSATION_ID_KEY, "conv-2"))
+			.call()
+			.chatResponse();
+
+		assertThat(response).isNotNull();
+		String assistantReply = response.getResult().getOutput().getText();
+		System.out.println("Assistant reply: " + assistantReply);
+
+		assertThat(assistantReply.toLowerCase()).doesNotContain("blue");
+	}
+
+}