Q: Someone I know is visiting me from outside the U.S. so they only get my iMessages when connected to Wi-Fi. However, if I’ve sent something and it doesn’t say “Delivered,” if I then delete it will that cancel the sending of the message or will they still receive it when they get back onto Wi-Fi?
A: Basically, no, the message won’t be canceled. Once you hit the ‘Send’ button on an iMessage, your iOS device is pretty much committed to sending it, and will try until it either fails to send it out itself (i.e. you have no network coverage), or it gets sent. In fact, even if you delete a message while it’s in the processing of “Sending…” you’re only removing your local copy on that particular device; the message itself will still get sent, and even appear on other devices that you have enabled for your iMessage account, such as a Mac or iPad.
Further, if you’re using an iPhone and have the “Send as SMS” option enabled in your Messages Settings, any messages that can’t be delivered by iMessage will eventually be sent as normal text messages. Deleting them from the Messages conversation view won’t even stop that process from occurring. There’s basically no way to stop a message from being delivered once sent it, although if the message fails to be sent, you’ll see an error icon and a “Not Delivered” status on the message.
At this point the message won’t be re-sent unless you tap the error icon and choose to re-send it manually. Note, however, that this normally only happens if your iPhone is out of network coverage and can’t even submit the message to Apple’s servers. If you’ve ever sent a message that you want to take back right away, in some cases putting your iPhone in Airplane Mode may stop the message from being sent, but you’ll usually need to wait about five minutes before it gives up trying, and of course you have to do this before the message gets sent out in the first place — often only a time window of mere seconds if you’re only sending a simple text.