diff --git a/src/config/mcp_factory.rs b/src/config/mcp_factory.rs
index 3bc3508..8a05dc2 100644
--- a/src/config/mcp_factory.rs
+++ b/src/config/mcp_factory.rs
@@ -1,8 +1,9 @@
 use crate::mcp::{
-    ConnectedServer, JsonField, McpServer, McpTransportType, oauth, spawn_mcp_server,
+    ConnectedServer, JsonField, McpServer, McpTransportType, is_auth_required_error, oauth,
+    spawn_mcp_server,
 };
 
-use anyhow::Result;
+use anyhow::{Result, anyhow};
 use parking_lot::Mutex;
 use std::collections::HashMap;
 use std::path::Path;
@@ -106,7 +107,18 @@ impl McpFactory {
         } else {
             None
         };
-        let handle = spawn_mcp_server(spec, log_path, bearer_token).await?;
+        let handle = spawn_mcp_server(spec, log_path, bearer_token)
+            .await
+            .map_err(|e| {
+                if is_auth_required_error(&e) {
+                    anyhow!(
+                        "MCP server '{name}' requires OAuth authentication. \
+                         Run `coyote --auth-mcp {name}` or `.mcp auth {name}` in the REPL to authenticate."
+                    )
+                } else {
+                    e
+                }
+            })?;
         self.insert_active(key, &handle);
         Ok(handle)
     }
diff --git a/src/mcp/mod.rs b/src/mcp/mod.rs
index f9aefca..710f641 100644
--- a/src/mcp/mod.rs
+++ b/src/mcp/mod.rs
@@ -287,8 +287,7 @@ impl McpRegistry {
             Err(e) if is_auth_required_error(&e) => {
                 warn!(
                     "MCP server '{id}' requires OAuth authentication. \
-                     Run `coyote --auth-mcp {id}` or `.mcp auth {id}` in the REPL to authenticate, \
-                     then restart Coyote."
+                     Run `coyote --auth-mcp {id}` or `.mcp auth {id}` in the REPL to authenticate."
                 );
                 return Ok(None);
             }
@@ -409,7 +408,7 @@ fn merge_bearer_token(
     }
 }
 
-fn is_auth_required_error(e: &Error) -> bool {
+pub(crate) fn is_auth_required_error(e: &Error) -> bool {
     e.chain()
         .any(|cause| cause.to_string().contains("Auth required"))
 }
diff --git a/src/repl/mod.rs b/src/repl/mod.rs
index 28d762d..10ca56b 100644
--- a/src/repl/mod.rs
+++ b/src/repl/mod.rs
@@ -653,10 +653,7 @@ pub async fn run_repl_command(
                                             callback_port,
                                         )
                                         .await?;
-                                        println!(
-                                            "Authentication saved. \
-                                             Restart Coyote to connect to '{server_name}'."
-                                        );
+                                        println!("Authentication saved.");
                                     }
                                 }
                             }