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I went into Settings > Messages > Learn More and it says that iMessage only works in Wifi mode. I am on Wifi and I have been trying to send iMessages to another person. Each time I send it "delivered" appears under the message. The other person calls me saying that she has not been receiving my iMessages. However, when I turn off iMessage in Settings > Messages, she starts responding to me, implying that regular SMS messages work. I am wondering whether the iMessages that I've sent have disappeared forever or will she start downloading the undelivered iMessages them when she attains wifi access?

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    iMessage can act weird when it thinks someone should be on iMessage, but isn't. However, the fact that they are being "delivered" would make me wonder if something else is going on. Is it possible that she has an iPad or Mac which is receiving the messages even though her iPhone is not able to? Commented Mar 19, 2015 at 3:12
  • Recently, I've found that even if my Mac picks up an iMsg, if my phone is off or on airplane, I do get the msg on my phone later. I used to find them on my Mac when I got home. idk if that's an Apple or ISP change, though.
    – Tetsujin
    Commented Mar 19, 2015 at 20:48
  • iMsg works on network too, btw, not just wifi
    – Tetsujin
    Commented Mar 19, 2015 at 20:49

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My guess is that you both need to be on wifi, or you need to restart BOTH of your devices.

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