diff --git a/server/src/http/mcp/wizard_tools.rs b/server/src/http/mcp/wizard_tools.rs
index 183249b2..da5319c0 100644
--- a/server/src/http/mcp/wizard_tools.rs
+++ b/server/src/http/mcp/wizard_tools.rs
@@ -152,22 +152,67 @@ pub(super) fn tool_wizard_generate(args: &Value, ctx: &AppContext) -> Result<Str
     ))
 }
 
+/// Return true if the project directory has no meaningful source files.
+fn is_bare_project(project_root: &Path) -> bool {
+    let dominated_by_storkit = std::fs::read_dir(project_root)
+        .ok()
+        .map(|entries| {
+            let names: Vec<String> = entries
+                .filter_map(|e| e.ok())
+                .map(|e| e.file_name().to_string_lossy().to_string())
+                .collect();
+            // A bare project only has storkit scaffolding and no real code
+            names.iter().all(|n| {
+                n.starts_with('.')
+                    || n == "CLAUDE.md"
+                    || n == "LICENSE"
+                    || n == "README.md"
+                    || n == "script"
+                    || n == "store.json"
+            })
+        })
+        .unwrap_or(true);
+    dominated_by_storkit
+}
+
 /// Return a generation hint for a step based on the project root.
 fn generation_hint(step: WizardStep, project_root: &Path) -> String {
+    let bare = is_bare_project(project_root);
+
     match step {
         WizardStep::Context => {
-            "Read the project source tree and generate a `.storkit/specs/00_CONTEXT.md` describing:\n\
-             - High-level goal of the project\n\
-             - Core features\n\
-             - Domain concepts and entities\n\
-             - Glossary of abbreviations and technical terms".to_string()
+            if bare {
+                "This is a bare project with no existing code. Ask the user what they want \
+                 to build — the project's purpose, goals, target users, and key features. \
+                 Then generate `.storkit/specs/00_CONTEXT.md` from their answers covering:\n\
+                 - High-level goal of the project\n\
+                 - Core features\n\
+                 - Domain concepts and entities\n\
+                 - Glossary of abbreviations and technical terms".to_string()
+            } else {
+                "Read the project source tree and generate a `.storkit/specs/00_CONTEXT.md` describing:\n\
+                 - High-level goal of the project\n\
+                 - Core features\n\
+                 - Domain concepts and entities\n\
+                 - Glossary of abbreviations and technical terms".to_string()
+            }
         }
         WizardStep::Stack => {
-            "Read the project source tree and generate a `.storkit/specs/tech/STACK.md` describing:\n\
-             - Language, frameworks, and runtimes\n\
-             - Coding standards and linting rules\n\
-             - Quality gates (commands that must pass before merging)\n\
-             - Approved libraries and their purpose".to_string()
+            if bare {
+                "This is a bare project with no existing code. Ask the user what language, \
+                 frameworks, and tools they plan to use. Then generate `.storkit/specs/tech/STACK.md` \
+                 from their answers covering:\n\
+                 - Language, frameworks, and runtimes\n\
+                 - Coding standards and linting rules\n\
+                 - Quality gates (commands that must pass before merging)\n\
+                 - Approved libraries and their purpose".to_string()
+            } else {
+                "Read the project source tree and generate a `.storkit/specs/tech/STACK.md` describing:\n\
+                 - Language, frameworks, and runtimes\n\
+                 - Coding standards and linting rules\n\
+                 - Quality gates (commands that must pass before merging)\n\
+                 - Approved libraries and their purpose".to_string()
+            }
         }
         WizardStep::TestScript => {
             let has_cargo = project_root.join("Cargo.toml").exists();