diff --git a/pkg/agent/core.go b/pkg/agent/core.go
index aacc306..7fb384f 100644
--- a/pkg/agent/core.go
+++ b/pkg/agent/core.go
@@ -65,9 +65,11 @@ func BuildRuntime(cfg *config.Config, d tools.Dispatcher, cwd string, env []stri
 		for k, v := range cfg.Hooks {
 			hooks[k] = []string(v)
 		}
+		fmt.Fprintf(os.Stderr, "[DEBUG BuildRuntime] cfg.Prompt.IsExec=%v len(Value)=%d\n", cfg.Prompt.IsExec, len(cfg.Prompt.Value))
 		if resolved, err := resolvePrompt(cfg.Prompt, cwd, env); err != nil {
 			fmt.Fprintf(os.Stderr, "resolve prompt: %v\n", err)
 		} else {
+			fmt.Fprintf(os.Stderr, "[DEBUG BuildRuntime] preamble len=%d\n", len(resolved))
 			preamble = resolved
 		}
 		genParams = backend.GenerationParams{
diff --git a/pkg/agent/core_test.go b/pkg/agent/core_test.go
index 3e395d3..5cef1cd 100644
--- a/pkg/agent/core_test.go
+++ b/pkg/agent/core_test.go
@@ -2473,6 +2473,29 @@ func TestBuildRuntime_ExecPrompt(t *testing.T) {
 	}
 }
 
+func TestBuildRuntime_ExecPromptFileResolution(t *testing.T) {
+	dir := setupCfgDir(t)
+	// Create a prompts directory with a test prompt file.
+	promptsDir := filepath.Join(dir, "prompts")
+	os.MkdirAll(promptsDir, 0o755)
+	os.WriteFile(filepath.Join(promptsDir, "test-prompt.md"), []byte("Hello ${PRIME_PLATFORM}"), 0o644)
+	t.Setenv("OLLIE_PROMPTS_PATH", promptsDir)
+
+	d := tools.NewDispatcher()
+	cfg := &config.Config{Prompt: config.Prompt{
+		Value:  []string{"test-prompt", "echo extra"},
+		IsExec: true,
+	}}
+	cwd := t.TempDir()
+	rt := BuildRuntime(cfg, d, cwd, PromptEnv(cwd))
+	if !strings.Contains(rt.Preamble, "Hello linux") {
+		t.Errorf("expected file content with expanded vars, got %q", rt.Preamble)
+	}
+	if !strings.Contains(rt.Preamble, "extra") {
+		t.Errorf("expected shell fallback output, got %q", rt.Preamble)
+	}
+}
+
 func TestBuildRuntime_ExecDispatchSuccess(t *testing.T) {
 	setupCfgDir(t)
 	d := &mockDispatcher{
diff --git a/pkg/agent/prompt_resolver.go b/pkg/agent/prompt_resolver.go
index baba838..c6ea7cc 100644
--- a/pkg/agent/prompt_resolver.go
+++ b/pkg/agent/prompt_resolver.go
@@ -29,6 +29,7 @@ func PromptEnv(cwd string) []string {
 	return []string{
 		"PRIME_CWD=" + cwd,
 		"PRIME_PLATFORM=" + platform,
+		"PRIME_DATE=" + time.Now().Format("2006-01-02"),
 		"PRIME_IS_GIT_REPO=" + isGitRepo,
 	}
 }
@@ -55,27 +56,52 @@ func resolvePrompt(p config.Prompt, cwd string, env []string) (string, error) {
 }
 
 func resolveExecPrompt(cmds []string, cwd string, env []string) (string, error) {
+	// Build env map for variable expansion.
+	fullEnv := append(os.Environ(), env...)
+	envMap := make(map[string]string, len(fullEnv))
+	for _, e := range fullEnv {
+		if k, v, ok := strings.Cut(e, "="); ok {
+			envMap[k] = v
+		}
+	}
+	expand := func(s string) string {
+		return os.Expand(s, func(key string) string {
+			return envMap[key]
+		})
+	}
+
 	var parts []string
-	for _, cmdStr := range cmds {
-		cmdStr = strings.TrimSpace(cmdStr)
-		if cmdStr == "" {
+	fmt.Fprintf(os.Stderr, "[DEBUG resolveExecPrompt] %d entries\n", len(cmds))
+	for _, entry := range cmds {
+		entry = strings.TrimSpace(entry)
+		if entry == "" {
 			continue
 		}
+		fmt.Fprintf(os.Stderr, "[DEBUG resolveExecPrompt] entry=%q\n", entry)
+		// Try resolving as a prompt file first.
+		if content, ok := resolvePromptFile(entry, envMap, expand); ok {
+			fmt.Fprintf(os.Stderr, "[DEBUG resolveExecPrompt] -> file ok, len=%d\n", len(content))
+			if content != "" {
+				parts = append(parts, content)
+			}
+			continue
+		}
+		// Fall back to shell execution.
 		ctx, cancel := context.WithTimeout(context.Background(), 30*time.Second)
-		cmd := exec.CommandContext(ctx, "sh", "-c", cmdStr)
+		cmd := exec.CommandContext(ctx, "sh", "-c", entry)
 		if cwd != "" {
 			if info, err := os.Stat(cwd); err == nil && info.IsDir() {
 				cmd.Dir = cwd
 			}
 		}
-		cmd.Env = append(os.Environ(), env...)
+		cmd.Env = fullEnv
 		var stdout, stderr bytes.Buffer
 		cmd.Stdout = &stdout
 		cmd.Stderr = &stderr
 		err := cmd.Run()
 		cancel()
 		if err != nil {
-			return "", fmt.Errorf("prompt command %q failed: %v: %s", cmdStr, err, stderr.String())
+			return "", fmt.Errorf("prompt command %q failed: %v: %s", entry, err, stderr.String())
 		}
 		if out := strings.TrimRight(stdout.String(), "\n"); out != "" {
 			parts = append(parts, out)
@@ -84,6 +110,61 @@ func resolveExecPrompt(cmds []string, cwd string, env []string) (string, error)
 	return strings.Join(parts, "\n"), nil
 }
 
+// resolvePromptFile attempts to resolve entry as a prompt file.
+// It first checks if the entry (after env expansion) is an absolute path to an
+// existing file. Otherwise it searches OLLIE_PROMPTS_PATH directories for
+// entry and entry.md. Returns the file content (with env vars expanded) and
+// true if found.
+func resolvePromptFile(entry string, envMap map[string]string, expand func(string) string) (string, bool) {
+	expanded := expand(entry)
+
+	// If it contains shell metacharacters, it's a command, not a file name.
+	if strings.ContainsAny(expanded, "|&;<>()$`\\\"' \t") {
+		return "", false
+	}
+
+	// Try as absolute path.
+	if filepath.IsAbs(expanded) {
+		if info, err := os.Stat(expanded); err == nil && !info.IsDir() {
+			return readAndExpand(expanded, expand)
+		}
+		// Try with .md suffix.
+		if info, err := os.Stat(expanded + ".md"); err == nil && !info.IsDir() {
+			return readAndExpand(expanded+".md", expand)
+		}
+		return "", false
+	}
+
+	// Search OLLIE_PROMPTS_PATH.
+	promptsPath := envMap["OLLIE_PROMPTS_PATH"]
+	if promptsPath == "" {
+		return "", false
+	}
+	for _, dir := range filepath.SplitList(promptsPath) {
+		if dir == "" {
+			continue
+		}
+		for _, candidate := range []string{
+			filepath.Join(dir, expanded),
+			filepath.Join(dir, expanded+".md"),
+		} {
+			if info, err := os.Stat(candidate); err == nil && !info.IsDir() {
+				return readAndExpand(candidate, expand)
+			}
+		}
+	}
+	return "", false
+}
+
+func readAndExpand(path string, expand func(string) string) (string, bool) {
+	data, err := os.ReadFile(path)
+	if err != nil {
+		return "", false
+	}
+	content := strings.TrimRight(expand(string(data)), "\n")
+	return content, true
+}
+
 func resolveStringPrompt(prompt, cwd string, env []string) (string, error) {
 	if prompt == "" {
 		return "", nil