diff --git a/models/spring-ai-anthropic/src/test/java/org/springframework/ai/anthropic/AnthropicChatModelIT.java b/models/spring-ai-anthropic/src/test/java/org/springframework/ai/anthropic/AnthropicChatModelIT.java
index 3f2b79bdf..eb9dd5d49 100644
--- a/models/spring-ai-anthropic/src/test/java/org/springframework/ai/anthropic/AnthropicChatModelIT.java
+++ b/models/spring-ai-anthropic/src/test/java/org/springframework/ai/anthropic/AnthropicChatModelIT.java
@@ -99,6 +99,25 @@ class AnthropicChatModelIT {
 		logger.info(response.toString());
 	}
 
+	@Test
+	void testMessageHistory() {
+		UserMessage userMessage = new UserMessage(
+				"Tell me about 3 famous pirates from the Golden Age of Piracy and why they did.");
+		SystemPromptTemplate systemPromptTemplate = new SystemPromptTemplate(systemResource);
+		Message systemMessage = systemPromptTemplate.createMessage(Map.of("name", "Bob", "voice", "pirate"));
+		Prompt prompt = new Prompt(List.of(userMessage, systemMessage),
+				AnthropicChatOptions.builder().withModel("claude-3-sonnet-20240229").build());
+
+		ChatResponse response = chatModel.call(prompt);
+		assertThat(response.getResult().getOutput().getContent()).containsAnyOf("Blackbeard", "Bartholomew");
+
+		var promptWithMessageHistory = new Prompt(List.of(new UserMessage("Dummy"), response.getResult().getOutput(),
+				new UserMessage("Repeat the last assistant message.")));
+		response = chatModel.call(promptWithMessageHistory);
+
+		assertThat(response.getResult().getOutput().getContent()).containsAnyOf("Blackbeard", "Bartholomew");
+	}
+
 	@Test
 	void streamingWithTokenUsage() {
 		var promptOptions = AnthropicChatOptions.builder().withTemperature(0f).build();
diff --git a/models/spring-ai-azure-openai/src/test/java/org/springframework/ai/azure/openai/AzureOpenAiChatModelIT.java b/models/spring-ai-azure-openai/src/test/java/org/springframework/ai/azure/openai/AzureOpenAiChatModelIT.java
index 957c8b9ce..24be25953 100644
--- a/models/spring-ai-azure-openai/src/test/java/org/springframework/ai/azure/openai/AzureOpenAiChatModelIT.java
+++ b/models/spring-ai-azure-openai/src/test/java/org/springframework/ai/azure/openai/AzureOpenAiChatModelIT.java
@@ -82,6 +82,32 @@ class AzureOpenAiChatModelIT {
 		assertThat(response.getResult().getOutput().getContent()).contains("Blackbeard");
 	}
 
+	@Test
+	void testMessageHistory() {
+
+		Message systemMessage = new SystemPromptTemplate("""
+				You are a helpful AI assistant. Your name is {name}.
+				You are an AI assistant that helps people find information.
+				Your name is {name}
+				You should reply to the user's request with your name and also in the style of a {voice}.
+				""").createMessage(Map.of("name", "Bob", "voice", "pirate"));
+
+		UserMessage userMessage = new UserMessage(
+				"Tell me about 3 famous pirates from the Golden Age of Piracy and why they did.");
+
+		Prompt prompt = new Prompt(List.of(userMessage, systemMessage));
+
+		ChatResponse response = chatModel.call(prompt);
+		assertThat(response.getResult().getOutput().getContent()).containsAnyOf("Blackbeard");
+
+		var promptWithMessageHistory = new Prompt(List.of(new UserMessage("Dummy"), response.getResult().getOutput(),
+				new UserMessage("Repeat the last assistant message.")));
+		response = chatModel.call(promptWithMessageHistory);
+
+		System.out.println(response.getResult().getOutput().getContent());
+		assertThat(response.getResult().getOutput().getContent()).containsAnyOf("Blackbeard");
+	}
+
 	@Test
 	void listOutputConverter() {
 		DefaultConversionService conversionService = new DefaultConversionService();
diff --git a/models/spring-ai-mistral-ai/src/test/java/org/springframework/ai/mistralai/MistralAiChatClientIT.java b/models/spring-ai-mistral-ai/src/test/java/org/springframework/ai/mistralai/MistralAiChatClientIT.java
index 8a526272a..81d45865c 100644
--- a/models/spring-ai-mistral-ai/src/test/java/org/springframework/ai/mistralai/MistralAiChatClientIT.java
+++ b/models/spring-ai-mistral-ai/src/test/java/org/springframework/ai/mistralai/MistralAiChatClientIT.java
@@ -27,7 +27,11 @@ import org.slf4j.LoggerFactory;
 import reactor.core.publisher.Flux;
 
 import org.springframework.ai.chat.client.ChatClient;
+import org.springframework.ai.chat.messages.Message;
+import org.springframework.ai.chat.messages.UserMessage;
 import org.springframework.ai.chat.model.ChatResponse;
+import org.springframework.ai.chat.prompt.Prompt;
+import org.springframework.ai.chat.prompt.SystemPromptTemplate;
 import org.springframework.ai.converter.BeanOutputConverter;
 import org.springframework.ai.converter.ListOutputConverter;
 import org.springframework.ai.mistralai.api.MistralAiApi;
@@ -73,6 +77,32 @@ class MistralAiChatClientIT {
 		assertThat(response.getResults().get(0).getOutput().getContent()).contains("Blackbeard");
 	}
 
+	@Test
+	void testMessageHistory() {
+
+		// @formatter:off
+		ChatResponse response = ChatClient.create(chatModel).prompt()
+				.system(s -> s.text(systemTextResource)
+						.param("name", "Bob")
+						.param("voice", "pirate"))
+				.user("Tell me about 3 famous pirates from the Golden Age of Piracy and what they did")
+				.call()
+				.chatResponse();
+		// @formatter:on
+		assertThat(response.getResult().getOutput().getContent()).containsAnyOf("Blackbeard");
+
+		// @formatter:off
+		response = ChatClient.create(chatModel).prompt()
+				.messages(List.of(new UserMessage("Dummy"), response.getResult().getOutput()))
+				.user("Repeat the last assistant message.")
+				.call()
+				.chatResponse();
+		// @formatter:on
+
+		logger.info("" + response);
+		assertThat(response.getResult().getOutput().getContent()).containsAnyOf("Blackbeard");
+	}
+
 	@Test
 	void listOutputConverterString() {
 		// @formatter:off
diff --git a/models/spring-ai-ollama/src/test/java/org/springframework/ai/ollama/OllamaChatModelIT.java b/models/spring-ai-ollama/src/test/java/org/springframework/ai/ollama/OllamaChatModelIT.java
index a773a0546..8cd56fead 100644
--- a/models/spring-ai-ollama/src/test/java/org/springframework/ai/ollama/OllamaChatModelIT.java
+++ b/models/spring-ai-ollama/src/test/java/org/springframework/ai/ollama/OllamaChatModelIT.java
@@ -101,6 +101,31 @@ class OllamaChatModelIT extends BaseOllamaIT {
 
 	}
 
+	@Test
+	void testMessageHistory() {
+
+		Message systemMessage = new SystemPromptTemplate("""
+				You are a helpful AI assistant. Your name is {name}.
+				You are an AI assistant that helps people find information.
+				Your name is {name}
+				You should reply to the user's request with your name and also in the style of a {voice}.
+				""").createMessage(Map.of("name", "Bob", "voice", "pirate"));
+
+		UserMessage userMessage = new UserMessage(
+				"Tell me about 3 famous pirates from the Golden Age of Piracy and why they did.");
+
+		Prompt prompt = new Prompt(List.of(userMessage, systemMessage));
+
+		ChatResponse response = chatModel.call(prompt);
+		assertThat(response.getResult().getOutput().getContent()).containsAnyOf("Bonny");
+
+		var promptWithMessageHistory = new Prompt(List.of(new UserMessage("Dummy"), response.getResult().getOutput(),
+				new UserMessage("Repeat the last assistant message.")));
+		response = chatModel.call(promptWithMessageHistory);
+
+		assertThat(response.getResult().getOutput().getContent()).containsAnyOf("Bonny");
+	}
+
 	@Test
 	void usageTest() {
 		Prompt prompt = new Prompt("Tell me a joke");
diff --git a/models/spring-ai-openai/src/test/java/org/springframework/ai/openai/chat/OpenAiChatModelIT.java b/models/spring-ai-openai/src/test/java/org/springframework/ai/openai/chat/OpenAiChatModelIT.java
index dff6e18b5..6bfc6faa5 100644
--- a/models/spring-ai-openai/src/test/java/org/springframework/ai/openai/chat/OpenAiChatModelIT.java
+++ b/models/spring-ai-openai/src/test/java/org/springframework/ai/openai/chat/OpenAiChatModelIT.java
@@ -84,6 +84,24 @@ class OpenAiChatModelIT extends AbstractIT {
 		// needs fine tuning... evaluateQuestionAndAnswer(request, response, false);
 	}
 
+	@Test
+	void testMessageHistory() {
+		UserMessage userMessage = new UserMessage(
+				"Tell me about 3 famous pirates from the Golden Age of Piracy and why they did.");
+		SystemPromptTemplate systemPromptTemplate = new SystemPromptTemplate(systemResource);
+		Message systemMessage = systemPromptTemplate.createMessage(Map.of("name", "Bob", "voice", "pirate"));
+		Prompt prompt = new Prompt(List.of(userMessage, systemMessage));
+
+		ChatResponse response = chatModel.call(prompt);
+		assertThat(response.getResult().getOutput().getContent()).containsAnyOf("Blackbeard", "Bartholomew");
+
+		var promptWithMessageHistory = new Prompt(List.of(new UserMessage("Dummy"), response.getResult().getOutput(),
+				new UserMessage("Repeat the last assistant message.")));
+		response = chatModel.call(promptWithMessageHistory);
+
+		assertThat(response.getResult().getOutput().getContent()).containsAnyOf("Blackbeard", "Bartholomew");
+	}
+
 	@Test
 	void streamCompletenessTest() throws InterruptedException {
 		UserMessage userMessage = new UserMessage(
diff --git a/models/spring-ai-vertex-ai-gemini/src/test/java/org/springframework/ai/vertexai/gemini/VertexAiGeminiChatModelIT.java b/models/spring-ai-vertex-ai-gemini/src/test/java/org/springframework/ai/vertexai/gemini/VertexAiGeminiChatModelIT.java
index 688291474..e74859d5d 100644
--- a/models/spring-ai-vertex-ai-gemini/src/test/java/org/springframework/ai/vertexai/gemini/VertexAiGeminiChatModelIT.java
+++ b/models/spring-ai-vertex-ai-gemini/src/test/java/org/springframework/ai/vertexai/gemini/VertexAiGeminiChatModelIT.java
@@ -75,8 +75,8 @@ class VertexAiGeminiChatModelIT {
 		ChatResponse response = chatModel.call(prompt);
 		assertThat(response.getResult().getOutput().getContent()).containsAnyOf("Blackbeard", "Bartholomew");
 
-		var promptWithMessageHistory = new Prompt(List.of(prompt.getInstructions().get(0),
-				response.getResult().getOutput(), new UserMessage("What was the answer from the previous question?")));
+		var promptWithMessageHistory = new Prompt(List.of(new UserMessage("Dummy"), prompt.getInstructions().get(1),
+				response.getResult().getOutput(), new UserMessage("Repeat the last assistant message.")));
 		response = chatModel.call(promptWithMessageHistory);
 
 		assertThat(response.getResult().getOutput().getContent()).containsAnyOf("Blackbeard", "Bartholomew");