diff --git a/cmd/run/run.go b/cmd/run/run.go
index 5668e06..c46a451 100644
--- a/cmd/run/run.go
+++ b/cmd/run/run.go
@@ -258,19 +258,19 @@ func NewRunCommand(cfg *command.Config) *cobra.Command {
 				return err
 			}
 
+			interactiveMode := true
 			initialPrompt := ""
-			singleShot := false
 			pipedContent := ""
 
 			if len(args) > 1 {
 				initialPrompt = strings.Join(args[1:], " ")
-				singleShot = true
+				interactiveMode = false
 			}
 
 			if isPipe(os.Stdin) {
 				promptFromPipe, _ := io.ReadAll(os.Stdin)
 				if len(promptFromPipe) > 0 {
-					singleShot = true
+					interactiveMode = false
 					pipedContent = strings.TrimSpace(string(promptFromPipe))
 					if initialPrompt != "" {
 						initialPrompt = initialPrompt + "\n" + pipedContent
@@ -289,28 +289,26 @@ func NewRunCommand(cfg *command.Config) *cobra.Command {
 				systemPrompt: systemPrompt,
 			}
 
-			// If a prompt file is passed, load the messages from the file, templating {{input}} from stdin
-			if pf != nil {
+			// If there is no prompt file, add the initialPrompt to the conversation.
+			// If a prompt file is passed, load the messages from the file, templating {{input}}
+			// using the initialPrompt.
+			if pf == nil {
+				conversation.AddMessage(azuremodels.ChatMessageRoleUser, initialPrompt)
+			} else {
+				interactiveMode = false
+
 				for _, m := range pf.Messages {
 					content := m.Content
-					if strings.ToLower(m.Role) == "user" {
-						content = strings.ReplaceAll(content, "{{input}}", initialPrompt)
-					}
 					switch strings.ToLower(m.Role) {
 					case "system":
-						if conversation.systemPrompt == "" {
-							conversation.systemPrompt = content
-						} else {
-							conversation.AddMessage(azuremodels.ChatMessageRoleSystem, content)
-						}
+						conversation.systemPrompt = content
 					case "user":
+						content = strings.ReplaceAll(content, "{{input}}", initialPrompt)
 						conversation.AddMessage(azuremodels.ChatMessageRoleUser, content)
 					case "assistant":
 						conversation.AddMessage(azuremodels.ChatMessageRoleAssistant, content)
 					}
 				}
-
-				initialPrompt = ""
 			}
 
 			mp := ModelParameters{}
@@ -326,63 +324,15 @@ func NewRunCommand(cfg *command.Config) *cobra.Command {
 			}
 
 			for {
-				prompt := ""
-				if initialPrompt != "" {
-					prompt = initialPrompt
-					initialPrompt = ""
-				}
-
-				if prompt == "" && pf == nil {
-					fmt.Printf(">>> ")
-					reader := bufio.NewReader(os.Stdin)
-					prompt, err = reader.ReadString('\n')
-					if err != nil {
-						return err
-					}
-				}
-
-				prompt = strings.TrimSpace(prompt)
-
-				if prompt == "" && pf == nil {
-					continue
-				}
-
-				if strings.HasPrefix(prompt, "/") {
-					if prompt == "/bye" || prompt == "/exit" || prompt == "/quit" {
+				if interactiveMode {
+					conversation, err = cmdHandler.ChatWithUser(conversation, mp)
+					if errors.Is(err, ErrExitChat) || errors.Is(err, io.EOF) {
 						break
+					} else if err != nil {
+						return err
 					}
-
-					if prompt == "/parameters" {
-						cmdHandler.handleParametersPrompt(conversation, mp)
-						continue
-					}
-
-					if prompt == "/reset" || prompt == "/clear" {
-						cmdHandler.handleResetPrompt(conversation)
-						continue
-					}
-
-					if strings.HasPrefix(prompt, "/set ") {
-						cmdHandler.handleSetPrompt(prompt, mp)
-						continue
-					}
-
-					if strings.HasPrefix(prompt, "/system-prompt ") {
-						conversation = cmdHandler.handleSystemPrompt(prompt, conversation)
-						continue
-					}
-
-					if prompt == "/help" {
-						cmdHandler.handleHelpPrompt()
-						continue
-					}
-
-					cmdHandler.handleUnrecognizedPrompt(prompt)
-					continue
 				}
 
-				conversation.AddMessage(azuremodels.ChatMessageRoleUser, prompt)
-
 				req := azuremodels.ChatCompletionOptions{
 					Messages: conversation.GetMessages(),
 					Model:    modelName,
@@ -431,7 +381,7 @@ func NewRunCommand(cfg *command.Config) *cobra.Command {
 
 				conversation.AddMessage(azuremodels.ChatMessageRoleAssistant, messageBuilder.String())
 
-				if singleShot || pf != nil {
+				if !interactiveMode {
 					break
 				}
 			}
@@ -618,3 +568,57 @@ func (h *runCommandHandler) handleCompletionChoice(choice azuremodels.ChatChoice
 func (h *runCommandHandler) writeToOut(message string) {
 	h.cfg.WriteToOut(message)
 }
+
+var ErrExitChat = errors.New("exiting chat")
+
+func (h *runCommandHandler) ChatWithUser(conversation Conversation, mp ModelParameters) (Conversation, error) {
+	fmt.Printf(">>> ")
+	reader := bufio.NewReader(os.Stdin)
+
+	prompt, err := reader.ReadString('\n')
+	if err != nil {
+		return conversation, err
+	}
+
+	prompt = strings.TrimSpace(prompt)
+	if prompt == "" {
+		return conversation, nil
+	}
+
+	if strings.HasPrefix(prompt, "/") {
+		if prompt == "/bye" || prompt == "/exit" || prompt == "/quit" {
+			return conversation, ErrExitChat
+		}
+
+		if prompt == "/parameters" {
+			h.handleParametersPrompt(conversation, mp)
+			return conversation, nil
+		}
+
+		if prompt == "/reset" || prompt == "/clear" {
+			h.handleResetPrompt(conversation)
+			return conversation, nil
+		}
+
+		if strings.HasPrefix(prompt, "/set ") {
+			h.handleSetPrompt(prompt, mp)
+			return conversation, nil
+		}
+
+		if strings.HasPrefix(prompt, "/system-prompt ") {
+			conversation = h.handleSystemPrompt(prompt, conversation)
+			return conversation, nil
+		}
+
+		if prompt == "/help" {
+			h.handleHelpPrompt()
+			return conversation, nil
+		}
+
+		h.handleUnrecognizedPrompt(prompt)
+		return conversation, nil
+	}
+
+	conversation.AddMessage(azuremodels.ChatMessageRoleUser, prompt)
+	return conversation, nil
+}
diff --git a/cmd/run/run_test.go b/cmd/run/run_test.go
index 27cc468..e930e77 100644
--- a/cmd/run/run_test.go
+++ b/cmd/run/run_test.go
@@ -139,7 +139,7 @@ messages:
 		_, err = runCmd.ExecuteC()
 		require.NoError(t, err)
 
-		require.Equal(t, 3, len(capturedReq.Messages))
+		require.Equal(t, 2, len(capturedReq.Messages))
 		require.Equal(t, "You are a text summarizer.", *capturedReq.Messages[0].Content)
 		require.Equal(t, "Hello there!", *capturedReq.Messages[1].Content)
 
@@ -220,7 +220,7 @@ messages:
 		_, err = runCmd.ExecuteC()
 		require.NoError(t, err)
 
-		require.Len(t, capturedReq.Messages, 3)
+		require.Len(t, capturedReq.Messages, 2)
 		require.Equal(t, "You are a text summarizer.", *capturedReq.Messages[0].Content)
 		require.Equal(t, initialPrompt+"\n"+piped, *capturedReq.Messages[1].Content) // {{input}} -> "Please summarize the provided text.\nHello there!"