diff --git a/crates/remote_server/src/transport.rs b/crates/remote_server/src/transport.rs
index c3e9ce9a12..7b275b0b38 100644
--- a/crates/remote_server/src/transport.rs
+++ b/crates/remote_server/src/transport.rs
@@ -111,11 +111,20 @@ impl Error {
     /// SSH remote-server failed banner, using `stage` to provide
     /// context-appropriate copy.
     pub fn user_facing_error(&self, stage: SetupStage) -> UserFacingError {
+        if matches!(self, Self::TimedOut) {
+            return UserFacingError {
+                body: format!("Timed out while trying to {}", stage.action_description()),
+                detail: Some(
+                    "Warp stopped waiting for the SSH extension to respond. Your SSH session is \
+                    still running, but advanced features are unavailable for now."
+                        .into(),
+                ),
+            };
+        }
+
         let body = format!("Failed to {}", stage.action_description());
         let detail = match self {
-            Self::TimedOut => {
-                Some("The operation timed out — check your network connection".into())
-            }
+            Self::TimedOut => unreachable!("handled above"),
             Self::UnsupportedOs { os } => Some(format!("Unsupported OS: {os}")),
             Self::UnsupportedArch { arch } => Some(format!("Unsupported architecture: {arch}")),
             Self::ScriptFailed { exit_code, stderr } => {
@@ -279,3 +288,7 @@ pub trait RemoteTransport: Send + Sync + std::fmt::Debug {
     /// the reconnect loop entirely.
     fn is_reconnectable(&self, exit_status: Option<&RemoteServerExitStatus>) -> bool;
 }
+
+#[cfg(test)]
+#[path = "transport_tests.rs"]
+mod tests;
diff --git a/crates/remote_server/src/transport_tests.rs b/crates/remote_server/src/transport_tests.rs
new file mode 100644
index 0000000000..6944450b4d
--- /dev/null
+++ b/crates/remote_server/src/transport_tests.rs
@@ -0,0 +1,26 @@
+use super::*;
+
+#[test]
+fn timed_out_error_copy_leads_with_timeout() {
+    let error = Error::TimedOut.user_facing_error(SetupStage::Launch);
+
+    assert_eq!(error.body, "Timed out while trying to start SSH extension");
+    assert_eq!(
+        error.detail.as_deref(),
+        Some(
+            "Warp stopped waiting for the SSH extension to respond. Your SSH session is \
+             still running, but advanced features are unavailable for now."
+        )
+    );
+}
+
+#[test]
+fn non_timeout_error_copy_still_leads_with_failure() {
+    let error = Error::UnsupportedOs {
+        os: "plan9".to_string(),
+    }
+    .user_facing_error(SetupStage::CheckBinary);
+
+    assert_eq!(error.body, "Failed to verify SSH extension");
+    assert_eq!(error.detail.as_deref(), Some("Unsupported OS: plan9"));
+}