diff --git a/.unreleased/LLT-5607-reduce_derp_conn_warnings b/.unreleased/LLT-5607-reduce_derp_conn_warnings
new file mode 100644
index 000000000..e69de29bb
diff --git a/crates/telio-relay/src/derp.rs b/crates/telio-relay/src/derp.rs
index 7f9e8f50f..860b47537 100644
--- a/crates/telio-relay/src/derp.rs
+++ b/crates/telio-relay/src/derp.rs
@@ -273,7 +273,14 @@ impl State {
                         break (server, conn);
                     }
                     Err(err) => {
-                        telio_log_warn!("({}) Failed to connect: {}", Self::NAME, err);
+                        if config.servers.current_server_num == config.servers.servers.len() {
+                            telio_log_warn!(
+                                "({}) Failed to connect to any of {} servers: {}",
+                                Self::NAME,
+                                config.servers.servers.len(),
+                                err
+                            );
+                        }
                         last_disconnection_reason = err.into();
                         continue;
                     }
diff --git a/crates/telio-sockets/src/protector/windows.rs b/crates/telio-sockets/src/protector/windows.rs
index e34ad1d3b..7d7d032a1 100644
--- a/crates/telio-sockets/src/protector/windows.rs
+++ b/crates/telio-sockets/src/protector/windows.rs
@@ -4,7 +4,7 @@ use std::io::{self, Result};
 use std::net::Ipv4Addr;
 use std::os::windows::io::RawSocket;
 use std::sync::Arc;
-use telio_utils::{telio_log_debug, telio_log_error, telio_log_warn};
+use telio_utils::{telio_log_debug, telio_log_error, telio_log_trace, telio_log_warn};
 use tokio::sync::mpsc::{self, Sender};
 use tokio::sync::Notify;
 use tokio::task::JoinHandle;
@@ -78,6 +78,7 @@ struct Sockets {
     tunnel_interface: Option<u64>,
     default_interface: Option<Interface>,
     notify: Arc<Notify>,
+    last_default_interface_error: Option<io::Error>,
 }
 
 impl Sockets {
@@ -87,6 +88,7 @@ impl Sockets {
             tunnel_interface: None,
             default_interface: None,
             notify: Arc::new(Notify::new()),
+            last_default_interface_error: None,
         }
     }
 
@@ -99,9 +101,22 @@ impl Sockets {
             return;
         }
         let new_default_interface = match get_default_interface(tunnel_interface) {
-            Ok(def) => Some(def),
+            Ok(def) => {
+                self.last_default_interface_error = None;
+                Some(def)
+            }
             Err(e) => {
-                telio_log_warn!("Failed to get default interface {}", e);
+                if self
+                    .last_default_interface_error
+                    .as_ref()
+                    .map(|old_err| old_err.kind() != e.kind())
+                    .unwrap_or(true)
+                {
+                    telio_log_warn!("Failed to get default interface: {}", e);
+                    self.last_default_interface_error = Some(e);
+                } else {
+                    telio_log_trace!("Failed to get default interface");
+                }
                 return;
             }
         };