diff --git a/rust/connlib/tunnel/src/gateway.rs b/rust/connlib/tunnel/src/gateway.rs
index ebb95b921..a9ef9bf4b 100644
--- a/rust/connlib/tunnel/src/gateway.rs
+++ b/rust/connlib/tunnel/src/gateway.rs
@@ -98,7 +98,7 @@ impl GatewayState {
 
         let packet = peer
             .translate_inbound(packet, now)
-            .context("Failed to translate packet")?;
+            .context("Failed to translate inbound packet")?;
 
         let Some(encrypted_packet) = self
             .node
@@ -156,7 +156,7 @@ impl GatewayState {
 
         let packet = peer
             .translate_outbound(packet, now)
-            .context("Failed to translate packet")?;
+            .context("Failed to translate outbound packet")?;
 
         Ok(Some(packet))
     }
diff --git a/rust/connlib/tunnel/src/peer.rs b/rust/connlib/tunnel/src/peer.rs
index 436b77895..c65a20e2f 100644
--- a/rust/connlib/tunnel/src/peer.rs
+++ b/rust/connlib/tunnel/src/peer.rs
@@ -337,7 +337,7 @@ impl ClientOnGateway {
 
         let mut packet = packet
             .translate_destination(self.ipv4, self.ipv6, source_protocol, real_ip)
-            .context("Failed to translate packet")?;
+            .context("Failed to translate packet to new destination")?;
         packet.update_checksum();
 
         Ok(packet)
@@ -375,7 +375,9 @@ impl ClientOnGateway {
             TranslateIncomingResult::NoNatSession => return Ok(packet),
         };
 
-        let mut packet = packet.translate_source(self.ipv4, self.ipv6, proto, ip)?;
+        let mut packet = packet
+            .translate_source(self.ipv4, self.ipv6, proto, ip)
+            .context("Failed to translate packet to new source")?;
         packet.update_checksum();
 
         Ok(packet)