diff --git a/kotlin/android/app/src/main/java/dev/firezone/android/features/session/ui/SessionViewModel.kt b/kotlin/android/app/src/main/java/dev/firezone/android/features/session/ui/SessionViewModel.kt
index c2813e334..7e6c3f82d 100644
--- a/kotlin/android/app/src/main/java/dev/firezone/android/features/session/ui/SessionViewModel.kt
+++ b/kotlin/android/app/src/main/java/dev/firezone/android/features/session/ui/SessionViewModel.kt
@@ -58,11 +58,6 @@ internal class SessionViewModel
                             resources = resources,
                         )
                 }
-
-                override fun onError(error: String): Boolean {
-                    // TODO("Not yet implemented")
-                    return true
-                }
             }
 
         fun connect(context: Context) {
diff --git a/kotlin/android/app/src/main/java/dev/firezone/android/tunnel/TunnelService.kt b/kotlin/android/app/src/main/java/dev/firezone/android/tunnel/TunnelService.kt
index 976b39cb0..f2640efac 100644
--- a/kotlin/android/app/src/main/java/dev/firezone/android/tunnel/TunnelService.kt
+++ b/kotlin/android/app/src/main/java/dev/firezone/android/tunnel/TunnelService.kt
@@ -100,11 +100,6 @@ class TunnelService : VpnService() {
                 return true
             }
 
-            override fun onError(error: String): Boolean {
-                Log.d(TAG, "onError: $error")
-                return true
-            }
-
             override fun onAddRoute(
                 addr: String,
                 prefix: Int,
diff --git a/kotlin/android/app/src/main/java/dev/firezone/android/tunnel/callback/ConnlibCallback.kt b/kotlin/android/app/src/main/java/dev/firezone/android/tunnel/callback/ConnlibCallback.kt
index 56199aa7e..5f21ab49f 100644
--- a/kotlin/android/app/src/main/java/dev/firezone/android/tunnel/callback/ConnlibCallback.kt
+++ b/kotlin/android/app/src/main/java/dev/firezone/android/tunnel/callback/ConnlibCallback.kt
@@ -24,7 +24,5 @@ interface ConnlibCallback {
 
     fun onDisconnect(error: String?): Boolean
 
-    fun onError(error: String): Boolean
-
     fun getSystemDefaultResolvers(): Array<ByteArray>
 }
diff --git a/kotlin/android/app/src/main/java/dev/firezone/android/tunnel/callback/TunnelListener.kt b/kotlin/android/app/src/main/java/dev/firezone/android/tunnel/callback/TunnelListener.kt
index 1367445aa..c56923f7e 100644
--- a/kotlin/android/app/src/main/java/dev/firezone/android/tunnel/callback/TunnelListener.kt
+++ b/kotlin/android/app/src/main/java/dev/firezone/android/tunnel/callback/TunnelListener.kt
@@ -8,6 +8,4 @@ interface TunnelListener {
     fun onTunnelStateUpdate(state: Tunnel.State)
 
     fun onResourcesUpdate(resources: List<Resource>)
-
-    fun onError(error: String): Boolean
 }
diff --git a/rust/connlib/clients/android/src/lib.rs b/rust/connlib/clients/android/src/lib.rs
index ac6734a13..db324dc6a 100644
--- a/rust/connlib/clients/android/src/lib.rs
+++ b/rust/connlib/clients/android/src/lib.rs
@@ -269,28 +269,9 @@ impl Callbacks for CallbackHandler {
         })
     }
 
-    fn on_error(&self, error: &Error) -> Result<(), Self::Error> {
-        self.env(|mut env| {
-            let error = env.new_string(error.to_string()).map_err(|source| {
-                CallbackError::NewStringFailed {
-                    name: "error",
-                    source,
-                }
-            })?;
-            call_method(
-                &mut env,
-                &self.callback_handler,
-                "onError",
-                "(Ljava/lang/String;)Z",
-                &[JValue::from(&error)],
-            )
-        })
-    }
-
     fn roll_log_file(&self) -> Option<PathBuf> {
         self.handle.roll_to_new_file().unwrap_or_else(|e| {
             tracing::debug!("Failed to roll over to new file: {e}");
-            let _ = self.on_error(&Error::LogFileRollError(e));
 
             None
         })
diff --git a/rust/connlib/clients/apple/src/lib.rs b/rust/connlib/clients/apple/src/lib.rs
index 7bcf91fc3..3c4f134ee 100644
--- a/rust/connlib/clients/apple/src/lib.rs
+++ b/rust/connlib/clients/apple/src/lib.rs
@@ -62,9 +62,6 @@ mod ffi {
 
         #[swift_bridge(swift_name = "getSystemDefaultResolvers")]
         fn get_system_default_resolvers(&self) -> String;
-
-        #[swift_bridge(swift_name = "onError")]
-        fn on_error(&self, error: String);
     }
 }
 
@@ -146,16 +143,9 @@ impl Callbacks for CallbackHandler {
         Ok(Some(resolvers))
     }
 
-    fn on_error(&self, error: &Error) -> Result<(), Self::Error> {
-        self.inner.on_error(error.to_string());
-        Ok(())
-    }
-
     fn roll_log_file(&self) -> Option<PathBuf> {
         self.handle.roll_to_new_file().unwrap_or_else(|e| {
-            tracing::debug!("Failed to roll over to new file: {e}");
-            let _ = self.on_error(&Error::LogFileRollError(e));
-
+            tracing::error!("Failed to roll over to new log file: {e}");
             None
         })
     }
diff --git a/rust/connlib/clients/shared/src/control.rs b/rust/connlib/clients/shared/src/control.rs
index d6d9a25f6..825b55be3 100644
--- a/rust/connlib/clients/shared/src/control.rs
+++ b/rust/connlib/clients/shared/src/control.rs
@@ -134,7 +134,7 @@ impl<CB: Callbacks + 'static> ControlPlane<CB> {
                     gateway_payload.domain_response,
                     gateway_public_key.0.into(),
                 ) {
-                    let _ = self.tunnel.callbacks().on_error(&e);
+                    tracing::debug!(error = ?e, "Error accepting connection: {e:#?}");
                 }
             }
             GatewayResponse::ResourceAccepted(gateway_payload) => {
@@ -142,7 +142,7 @@ impl<CB: Callbacks + 'static> ControlPlane<CB> {
                     .tunnel
                     .received_domain_parameters(resource_id, gateway_payload.domain_response)
                 {
-                    let _ = self.tunnel.callbacks().on_error(&e);
+                    tracing::debug!(error = ?e, "Error accepting resource: {e:#?}");
                 }
             }
         }
@@ -152,7 +152,6 @@ impl<CB: Callbacks + 'static> ControlPlane<CB> {
     pub fn add_resource(&self, resource_description: ResourceDescription) {
         if let Err(e) = self.tunnel.add_resource(resource_description) {
             tracing::error!(message = "Can't add resource", error = ?e);
-            let _ = self.tunnel.callbacks().on_error(&e);
         }
     }
 
@@ -217,7 +216,6 @@ impl<CB: Callbacks + 'static> ControlPlane<CB> {
 
             tunnel.cleanup_connection(resource_id);
             tracing::error!("Error request connection details: {err}");
-            let _ = tunnel.callbacks().on_error(&err);
         });
     }
 
@@ -231,7 +229,6 @@ impl<CB: Callbacks + 'static> ControlPlane<CB> {
         for candidate in candidates {
             if let Err(e) = self.tunnel.add_ice_candidate(gateway_id, candidate).await {
                 tracing::error!(err = ?e,"add_ice_candidate");
-                let _ = self.tunnel.callbacks().on_error(&e);
             }
         }
     }
@@ -259,7 +256,10 @@ impl<CB: Callbacks + 'static> ControlPlane<CB> {
 
                 tokio::spawn(async move {
                     if let Err(e) = upload(path.clone(), url).await {
-                        tracing::warn!("Failed to upload log file: {e}");
+                        tracing::warn!(
+                            "Failed to upload log file at path {path_display}: {e}. Not retrying.",
+                            path_display = path.display()
+                        );
                     }
                 });
             }
@@ -278,13 +278,7 @@ impl<CB: Callbacks + 'static> ControlPlane<CB> {
         match (reply_error.error, reference) {
             (ErrorInfo::Offline, Some(reference)) => {
                 let Ok(resource_id) = reference.parse::<ResourceId>() else {
-                    tracing::error!(
-                        "An offline error came back with a reference to a non-valid resource id"
-                    );
-                    let _ = self
-                        .tunnel
-                        .callbacks()
-                        .on_error(&Error::ControlProtocolError);
+                    tracing::warn!("The portal responded with an Offline error. Is the Resource associated with any online Gateways? Reference: {reference}");
                     return Ok(());
                 };
                 // TODO: Rate limit the number of attempts of getting the relays before just trying a local network connection
diff --git a/rust/connlib/clients/shared/src/lib.rs b/rust/connlib/clients/shared/src/lib.rs
index 744536725..12a99838c 100644
--- a/rust/connlib/clients/shared/src/lib.rs
+++ b/rust/connlib/clients/shared/src/lib.rs
@@ -212,17 +212,16 @@ where
                     let result = connection.start(vec!["client".to_owned()], || exponential_backoff.reset()).await;
                     tracing::warn!("Disconnected from the portal");
                     if let Err(e) = &result {
-                        tracing::warn!(error = ?e, "Portal connection error");
+                        tracing::error!(error = ?e, "Connection to portal failed. Starting retries with exponential backoff timer.");
                         if e.is_http_client_error() {
                             fatal_error!(result, runtime_stopper, &callbacks);
                         }
                     }
                     if let Some(t) = exponential_backoff.next_backoff() {
-                        tracing::warn!("Error connecting to portal, retrying in {} seconds", t.as_secs());
-                        let _ = callbacks.on_error(&result.err().unwrap_or(Error::PortalConnectionError(tokio_tungstenite::tungstenite::Error::ConnectionClosed)));
+                        tracing::error!("Connection to portal failed. Retrying connection to portal in {} seconds", t.as_secs());
                         tokio::time::sleep(t).await;
                     } else {
-                        tracing::error!("Connection to portal failed, giving up");
+                        tracing::error!("Connection to portal failed, giving up!");
                         Self::disconnect_inner(runtime_stopper, &callbacks, None);
                         break;
                     }
diff --git a/rust/connlib/shared/src/callbacks.rs b/rust/connlib/shared/src/callbacks.rs
index 2bb48406b..cc4d096ea 100644
--- a/rust/connlib/shared/src/callbacks.rs
+++ b/rust/connlib/shared/src/callbacks.rs
@@ -64,12 +64,6 @@ pub trait Callbacks: Clone + Send + Sync {
         std::process::exit(0);
     }
 
-    /// Called when there's a recoverable error.
-    fn on_error(&self, error: &crate::Error) -> Result<(), Self::Error> {
-        tracing::warn!(error = ?error);
-        Ok(())
-    }
-
     /// Returns the system's default resolver
     fn get_system_default_resolvers(&self) -> Result<Option<Vec<IpAddr>>, Self::Error> {
         Ok(None)
diff --git a/rust/connlib/shared/src/callbacks_error_facade.rs b/rust/connlib/shared/src/callbacks_error_facade.rs
index 7a5e5c9e0..efb7d99e9 100644
--- a/rust/connlib/shared/src/callbacks_error_facade.rs
+++ b/rust/connlib/shared/src/callbacks_error_facade.rs
@@ -81,14 +81,6 @@ impl<CB: Callbacks> Callbacks for CallbackErrorFacade<CB> {
         Ok(())
     }
 
-    fn on_error(&self, error: &Error) -> Result<()> {
-        if let Err(err) = self.0.on_error(error) {
-            tracing::error!(?err, "`on_error` failed");
-        }
-        // There's nothing we really want to do if `on_error` fails.
-        Ok(())
-    }
-
     fn roll_log_file(&self) -> Option<PathBuf> {
         self.0.roll_log_file()
     }
diff --git a/rust/connlib/shared/src/control.rs b/rust/connlib/shared/src/control.rs
index 8b3baa0c1..89b2b22a2 100644
--- a/rust/connlib/shared/src/control.rs
+++ b/rust/connlib/shared/src/control.rs
@@ -227,7 +227,7 @@ where
                         ReplyMessage::PhxReply(phx_reply) => match phx_reply {
                             // TODO: Here we should pass error info to a subscriber
                             PhxReply::Error(info) => {
-                                tracing::warn!("Portal error: {info:?}");
+                                tracing::debug!("Portal error: {info:?}");
                                 handler(Err(ErrorReply { error: info }), m.reference, m.topic).await
                             }
                             PhxReply::Ok(reply) => match reply {
diff --git a/rust/connlib/tunnel/src/control_protocol.rs b/rust/connlib/tunnel/src/control_protocol.rs
index 0181ecdb5..e547ed50d 100644
--- a/rust/connlib/tunnel/src/control_protocol.rs
+++ b/rust/connlib/tunnel/src/control_protocol.rs
@@ -154,7 +154,6 @@ fn insert_peers<TId: Copy, TTransform>(
 fn start_handlers<TId, TTransform, TRoleState>(
     tunnel: Arc<Tunnel<impl Callbacks + 'static, TRoleState>>,
     device: Arc<ArcSwapOption<Device>>,
-    callbacks: impl Callbacks + 'static,
     peer: Arc<Peer<TId, TTransform>>,
     ice: Arc<RTCIceTransport>,
     peer_receiver: tokio::sync::mpsc::Receiver<Bytes>,
@@ -180,12 +179,7 @@ fn start_handlers<TId, TTransform, TRoleState>(
             let Some(ep) = ice.new_endpoint(Box::new(|_| true)).await else {
                 return;
             };
-            tokio::spawn(peer_handler::start_peer_handler(
-                device,
-                callbacks,
-                peer,
-                ep.clone(),
-            ));
+            tokio::spawn(peer_handler::start_peer_handler(device, peer, ep.clone()));
             tokio::spawn(peer_handler::handle_packet(ep, peer_receiver));
         }
     });
diff --git a/rust/connlib/tunnel/src/control_protocol/client.rs b/rust/connlib/tunnel/src/control_protocol/client.rs
index 8b5204723..fdda4f2e7 100644
--- a/rust/connlib/tunnel/src/control_protocol/client.rs
+++ b/rust/connlib/tunnel/src/control_protocol/client.rs
@@ -171,7 +171,6 @@ where
         start_handlers(
             Arc::clone(self),
             Arc::clone(&self.device),
-            self.callbacks.clone(),
             peer.clone(),
             ice,
             peer_receiver,
diff --git a/rust/connlib/tunnel/src/control_protocol/gateway.rs b/rust/connlib/tunnel/src/control_protocol/gateway.rs
index 3ba30886f..b5de9744b 100644
--- a/rust/connlib/tunnel/src/control_protocol/gateway.rs
+++ b/rust/connlib/tunnel/src/control_protocol/gateway.rs
@@ -245,7 +245,6 @@ where
         start_handlers(
             Arc::clone(self),
             Arc::clone(&self.device),
-            self.callbacks.clone(),
             peer.clone(),
             ice,
             peer_receiver,
diff --git a/rust/connlib/tunnel/src/lib.rs b/rust/connlib/tunnel/src/lib.rs
index 708481ee9..97925b3f2 100644
--- a/rust/connlib/tunnel/src/lib.rs
+++ b/rust/connlib/tunnel/src/lib.rs
@@ -328,11 +328,9 @@ where
 
                 if let Some(conn) = self.peer_connections.lock().remove(&conn_id) {
                     tokio::spawn({
-                        let callbacks = self.callbacks.clone();
                         async move {
                             if let Err(e) = conn.stop().await {
                                 tracing::warn!(%conn_id, error = ?e, "Can't close peer");
-                                let _ = callbacks.on_error(&e.into());
                             }
                         }
                     });
@@ -364,7 +362,6 @@ where
 
                 if let Err(e) = device.refresh_mtu() {
                     tracing::error!(error = ?e, "refresh_mtu");
-                    let _ = self.callbacks.on_error(&e);
                 }
             }
 
diff --git a/rust/connlib/tunnel/src/peer.rs b/rust/connlib/tunnel/src/peer.rs
index ce64493af..3c0ff7e59 100644
--- a/rust/connlib/tunnel/src/peer.rs
+++ b/rust/connlib/tunnel/src/peer.rs
@@ -173,7 +173,7 @@ where
         let (packet, addr) = self.transform.packet_untransform(&addr, packet)?;
 
         if !self.is_allowed(addr) {
-            tracing::warn!("packet not allowed: {addr}");
+            tracing::debug!("A packet was seen from the tunnel with a destination address we didn't expect: {addr}");
             return Ok(None);
         }
 
diff --git a/rust/connlib/tunnel/src/peer_handler.rs b/rust/connlib/tunnel/src/peer_handler.rs
index 2fffda9cb..cad000065 100644
--- a/rust/connlib/tunnel/src/peer_handler.rs
+++ b/rust/connlib/tunnel/src/peer_handler.rs
@@ -4,7 +4,6 @@ use std::time::Duration;
 
 use arc_swap::ArcSwapOption;
 use bytes::Bytes;
-use connlib_shared::Callbacks;
 use webrtc::mux::endpoint::Endpoint;
 use webrtc::util::Conn;
 
@@ -14,7 +13,6 @@ use crate::{peer::Peer, MAX_UDP_SIZE};
 
 pub(crate) async fn start_peer_handler<TId, TTransform>(
     device: Arc<ArcSwapOption<Device>>,
-    callbacks: impl Callbacks + 'static,
     peer: Arc<Peer<TId, TTransform>>,
     channel: Arc<Endpoint>,
 ) where
@@ -27,7 +25,7 @@ pub(crate) async fn start_peer_handler<TId, TTransform>(
             tokio::time::sleep(Duration::from_millis(100)).await;
             continue;
         };
-        let result = peer_handler(&callbacks, &peer, channel.clone(), &device).await;
+        let result = peer_handler(&peer, channel.clone(), &device).await;
 
         if matches!(result, Err(ref err) if err.raw_os_error() == Some(9)) {
             tracing::warn!("bad_file_descriptor");
@@ -45,7 +43,6 @@ pub(crate) async fn start_peer_handler<TId, TTransform>(
 }
 
 async fn peer_handler<TId, TTransform>(
-    callbacks: &impl Callbacks,
     peer: &Arc<Peer<TId, TTransform>>,
     channel: Arc<Endpoint>,
     device: &Device,
@@ -83,7 +80,6 @@ where
             Ok(None) => {}
             Err(other) => {
                 tracing::error!(error = ?other, "failed to handle peer packet");
-                let _ = callbacks.on_error(&other);
             }
         }
     }
diff --git a/rust/linux-client/src/main.rs b/rust/linux-client/src/main.rs
index e5057b715..158d76527 100644
--- a/rust/linux-client/src/main.rs
+++ b/rust/linux-client/src/main.rs
@@ -1,6 +1,6 @@
 use anyhow::Result;
 use clap::Parser;
-use connlib_client_shared::{file_logger, Callbacks, Error, Session};
+use connlib_client_shared::{file_logger, Callbacks, Session};
 use firezone_cli_utils::{block_on_ctrl_c, setup_global_subscriber, CommonArgs};
 use secrecy::SecretString;
 use std::path::PathBuf;
@@ -43,8 +43,6 @@ impl Callbacks for CallbackHandler {
             .roll_to_new_file()
             .unwrap_or_else(|e| {
                 tracing::debug!("Failed to roll over to new file: {e}");
-                let _ = self.on_error(&Error::LogFileRollError(e));
-
                 None
             })
     }
diff --git a/rust/windows-client/src-tauri/src/client/gui.rs b/rust/windows-client/src-tauri/src/client/gui.rs
index 65d4dbe01..f2af7fa1b 100755
--- a/rust/windows-client/src-tauri/src/client/gui.rs
+++ b/rust/windows-client/src-tauri/src/client/gui.rs
@@ -250,11 +250,6 @@ impl connlib_client_shared::Callbacks for CallbackHandler {
         Ok(())
     }
 
-    fn on_error(&self, error: &connlib_client_shared::Error) -> Result<(), Self::Error> {
-        tracing::error!("on_error not implemented. Error: {error:?}");
-        Ok(())
-    }
-
     fn on_tunnel_ready(&self) -> Result<(), Self::Error> {
         // TODO: implement
         tracing::info!("on_tunnel_ready");
@@ -274,7 +269,6 @@ impl connlib_client_shared::Callbacks for CallbackHandler {
     fn roll_log_file(&self) -> Option<PathBuf> {
         self.logger.roll_to_new_file().unwrap_or_else(|e| {
             tracing::debug!("Failed to roll over to new file: {e}");
-            let _ = self.on_error(&connlib_client_shared::Error::LogFileRollError(e));
 
             None
         })
diff --git a/swift/apple/FirezoneNetworkExtension/Adapter.swift b/swift/apple/FirezoneNetworkExtension/Adapter.swift
index e775385a0..1697761b6 100644
--- a/swift/apple/FirezoneNetworkExtension/Adapter.swift
+++ b/swift/apple/FirezoneNetworkExtension/Adapter.swift
@@ -544,8 +544,4 @@ extension Adapter: CallbackHandlerDelegate {
     self.logger.info("getSystemDefaultResolvers: \(resolvers)")
     return resolvers
   }
-
-  public func onError(error: String) {
-    self.logger.error("Internal connlib error: \(error, privacy: .public)")
-  }
 }
diff --git a/swift/apple/FirezoneNetworkExtension/CallbackHandler.swift b/swift/apple/FirezoneNetworkExtension/CallbackHandler.swift
index d8e1902f3..f2ee00915 100644
--- a/swift/apple/FirezoneNetworkExtension/CallbackHandler.swift
+++ b/swift/apple/FirezoneNetworkExtension/CallbackHandler.swift
@@ -27,7 +27,6 @@ public protocol CallbackHandlerDelegate: AnyObject {
   func onUpdateResources(resourceList: String)
   func onDisconnect(error: String?)
   func getSystemDefaultResolvers() -> [String]
-  func onError(error: String)
 }
 
 public class CallbackHandler {
@@ -92,9 +91,4 @@ public class CallbackHandler {
       return "[]".intoRustString()
     }
   }
-
-  func onError(error: RustString) {
-    logger.log("CallbackHandler.onError: \(error.toString(), privacy: .public)")
-    delegate?.onError(error: error.toString())
-  }
 }