Sending two messages at the same and having the first fail still sends the second

[turt2live]

Steps to reproduce

1. Send two messages
2. Ensure your server fails to send the first
3. Watch the second get sent (it should be blocked due to the error on the first)
4. Send another message
5. That message gets appropriately gated by the failed message

Outcome

What did you expect?

3 of my messages to fail to send, not 2.

What happened instead?

The first message sent okay. After it was sent, a new batch of messages was started: the second and third were sent at roughly the same time and due to a server crashing slowly ended up blocked for long enough to work. Once the second failed to send and the third sent, I started a new message (fourth) which appropriately got marked as failed to send.

Resolved by manually re-queuing the messages in the order I wanted them, and screenshotting the messages so the receipients knew what was going on :)

(this is what makes this bug nasty: we have a lot of code which tries to make sure order is preserved, and it broke that guarantee here, making the app lose a bit of user trust that it can safely send messages)

Operating system

Windows 10

Application version

No response

How did you install the app?

No response

Homeserver

t2l.io

Will you send logs?

Yes

[Johennes]

I'm upgrading this to S-Major. For one thing, this is part of what we've identified as "Chronic Issues". For another, sending messages appears to be critical functionality to me and manually re-queuing them in the correct order doesn't feel like a satisfactory workaround to me (especially since by the time you realize they were send in the wrong order, the damage is already done).

[ara4n]

(i don't think we expose UX to let the user manually re-queue them as a workaround, either? and certainly not reliably)