Apple Watch recordings not uploading when back on Wi-Fi.

As the title says, I recorded two messages on my Apple Watch while out and about without a phone or Wi‑Fi connection.

These two messages were queued in the app in orange, saying they would be uploaded when back on Wi‑Fi; however, they seem to be stuck there. I cannot get them to upload; there's nothing I can tap either on the watch or on my phone.

I recorded another message on my watch to see if that would kick off the uploading, but it didn't. Only the new message was uploaded, and the old messages are still shown as queuing.