diff --git a/src/config/request_context.rs b/src/config/request_context.rs
index dd0efef..5a5b192 100644
--- a/src/config/request_context.rs
+++ b/src/config/request_context.rs
@@ -2495,18 +2495,13 @@ impl RequestContext {
                 format!("Failed to scaffold skill at {}", path.display())
             })?;
         }
-
         let editor = app.editor()?;
         edit_file(&editor, &path)?;
-
-        if self.working_mode.is_repl() {
-            if is_new {
-                println!("✓ Created skill at '{}'.", path.display());
-            } else {
-                println!("✓ Saved skill at '{}'.", path.display());
-            }
+        if is_new {
+            println!("✓ Created skill at '{}'.", path.display());
+        } else {
+            println!("✓ Saved skill at '{}'.", path.display());
         }
-
         Ok(())
     }
 
diff --git a/src/main.rs b/src/main.rs
index 2eb65e4..9bc596b 100644
--- a/src/main.rs
+++ b/src/main.rs
@@ -197,7 +197,9 @@ async fn run(
         println!("{skills}");
         return Ok(());
     }
-    if let Some(name) = &cli.skill {
+    if let Some(name) = &cli.skill
+        && !paths::has_skill(name)
+    {
         let app = Arc::clone(&ctx.app.config);
         ctx.upsert_skill(app.as_ref(), name)?;
         return Ok(());
@@ -315,6 +317,10 @@ async fn run(
             .await?;
     }
 
+    if let Some(name) = &cli.skill {
+        ctx.load_skill_repl(name, abort_signal.clone()).await?;
+    }
+
     match is_repl {
         false => {
             let mut input = create_input(&ctx, text, &cli.file, abort_signal.clone()).await?;