diff --git a/bindings/rust/extended/s2n-tls/src/callbacks.rs b/bindings/rust/extended/s2n-tls/src/callbacks.rs
index 5d871c34844..c1d476ec1b8 100644
--- a/bindings/rust/extended/s2n-tls/src/callbacks.rs
+++ b/bindings/rust/extended/s2n-tls/src/callbacks.rs
@@ -51,15 +51,15 @@ where
     F: FnOnce(&mut Connection, &mut Context) -> T,
 {
     let raw = NonNull::new(conn_ptr).expect("connection should not be null");
-    let mut conn = Connection::from_raw(raw);
-    let mut config = conn.config().expect("config should not be null");
-    let context = config.context_mut();
-    let r = action(&mut conn, context);
     // Since this is a callback, it receives a pointer to the connection
     // but doesn't own that connection or control its lifecycle.
     // Do not drop / free the connection.
-    let _ = ManuallyDrop::new(conn);
-    r
+    // We must make the connection `ManuallyDrop` before `action`, otherwise a panic
+    // in `action` would cause the unwind mechanism to drop the connection.
+    let mut conn = ManuallyDrop::new(Connection::from_raw(raw));
+    let mut config = conn.config().expect("config should not be null");
+    let context = config.context_mut();
+    action(&mut conn, context)
 }
 
 /// A trait for the callback used to verify host name(s) during X509
@@ -100,3 +100,39 @@ pub(crate) unsafe fn verify_host(
         Err(_) => 0, // If the host name can't be parsed, fail closed.
     }
 }
+
+#[cfg(test)]
+mod tests {
+    use crate::{callbacks::with_context, config::Config, connection::Builder, enums::Mode};
+
+    // The temporary connection created in `with_context` should never be freed,
+    // even if customer code panics.
+    #[test]
+    fn panic_does_not_free_connection() -> Result<(), crate::error::Error> {
+        let config = Config::new();
+        let mut connection = config.build_connection(Mode::Server)?;
+
+        // 1 connection + 1 self reference
+        assert_eq!(config.test_get_refcount()?, 2);
+
+        let conn_ptr = connection.as_ptr();
+        let unwind_result = std::panic::catch_unwind(|| {
+            unsafe {
+                with_context(conn_ptr, |_conn, _context| {
+                    panic!("force unwind");
+                })
+            };
+        });
+
+        // a panic happened
+        assert!(unwind_result.is_err());
+
+        // the connection hasn't been freed yet
+        assert_eq!(config.test_get_refcount()?, 2);
+
+        drop(connection);
+        assert_eq!(config.test_get_refcount()?, 1);
+
+        Ok(())
+    }
+}