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I have done a bit of research, but I haven't found a satisfactory answer to this question.

Basically, I'd like to know what happens if I send a message to an offline Skype contact; will the message stay on my computer (or other device) and will be sent to the server, and subsequently to my contact, only when he/she will turn online? Or is it sent to the server as soon as I write it, and then sent to the recipient when he/she will be online, even if by that time I'm offline myself?

So, in the end, if I want to communicate with someone who's offline, can I do that or must I wait for him/her to be online?

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It is stored on your device and then sent to the other contact the next time you are both online.

Source: https://support.skype.com/en/faq/FA10646/will-my-instant-message-be-delivered-if-the-recipient-is-not-signed-in-to-skype

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    +1 for also listing the source of the information. – Hennes Aug 13 '13 at 14:32
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    Thanks, it seems rather useless this way... So if I'm writing a message from the computer, and the next time I'm seeing the contact I will be using my cellphone, the messages are not delivered, I suppose? – Sekhemty Aug 13 '13 at 16:44
  • It appears to be that way. – Jack Aug 13 '13 at 16:45
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The way IM works now both contacts have to be online at the same time for a message to be delivered.

But if you send a message to a contact who is offline, it will be stored by Skype on your device and sent to the recipient next time you are both online simultaneously. So stay online as much as you can !

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