diff --git a/rust/connlib/clients/shared/src/callbacks.rs b/rust/connlib/clients/shared/src/callbacks.rs
index ac9bb16a0..93aebe56c 100644
--- a/rust/connlib/clients/shared/src/callbacks.rs
+++ b/rust/connlib/clients/shared/src/callbacks.rs
@@ -48,3 +48,13 @@ pub enum DisconnectError {
     #[error("connection to the portal failed: {0}")]
     PortalConnectionFailed(#[from] phoenix_channel::Error),
 }
+
+impl DisconnectError {
+    pub fn is_authentication_error(&self) -> bool {
+        let Self::PortalConnectionFailed(e) = self else {
+            return false;
+        };
+
+        e.is_authentication_error()
+    }
+}
diff --git a/rust/connlib/clients/shared/src/lib.rs b/rust/connlib/clients/shared/src/lib.rs
index 0630f05f5..202b7c178 100644
--- a/rust/connlib/clients/shared/src/lib.rs
+++ b/rust/connlib/clients/shared/src/lib.rs
@@ -150,7 +150,15 @@ async fn connect_supervisor<CB>(
             tracing::info!("connlib exited gracefully");
         }
         Ok(Err(e)) => {
-            telemetry::capture_error(&e);
+            if e.is_authentication_error() {
+                telemetry::capture_message(
+                    "Portal authentication error",
+                    telemetry::Level::Warning,
+                );
+            } else {
+                telemetry::capture_error(&e);
+            }
+
             tracing::error!("connlib failed: {e}");
             callbacks.on_disconnect(&e);
         }
diff --git a/rust/headless-client/src/lib.rs b/rust/headless-client/src/lib.rs
index 7fbeb3702..69c61a0b4 100644
--- a/rust/headless-client/src/lib.rs
+++ b/rust/headless-client/src/lib.rs
@@ -9,7 +9,7 @@
 //! Otherwise we would just make it a normal binary crate.
 
 use anyhow::{Context as _, Result};
-use connlib_client_shared::{Callbacks, DisconnectError};
+use connlib_client_shared::Callbacks;
 use connlib_model::ResourceView;
 use firezone_bin_shared::platform::DnsControlMethod;
 use std::{
@@ -97,16 +97,10 @@ pub struct CallbackHandler {
 impl Callbacks for CallbackHandler {
     fn on_disconnect(&self, error: &connlib_client_shared::DisconnectError) {
         tracing::error!(?error, "Got `on_disconnect` from connlib");
-        let is_authentication_error = if let DisconnectError::PortalConnectionFailed(error) = error
-        {
-            error.is_authentication_error()
-        } else {
-            false
-        };
         self.cb_tx
             .try_send(ConnlibMsg::OnDisconnect {
                 error_msg: error.to_string(),
-                is_authentication_error,
+                is_authentication_error: error.is_authentication_error(),
             })
             .expect("should be able to send OnDisconnect");
     }
diff --git a/rust/telemetry/src/lib.rs b/rust/telemetry/src/lib.rs
index ac3f1d759..c3c8e6d3d 100644
--- a/rust/telemetry/src/lib.rs
+++ b/rust/telemetry/src/lib.rs
@@ -2,8 +2,9 @@ use arc_swap::ArcSwapOption;
 use std::time::Duration;
 
 pub use sentry::{
-    add_breadcrumb, capture_error, configure_scope, end_session, end_session_with_status,
-    start_transaction, types::protocol::v7::SessionStatus, Breadcrumb, Hub, TransactionContext,
+    add_breadcrumb, capture_error, capture_message, configure_scope, end_session,
+    end_session_with_status, start_transaction, types::protocol::v7::SessionStatus, Breadcrumb,
+    Hub, Level, TransactionContext,
 };
 
 pub struct Dsn(&'static str);