IM i send to one of my friends is not yet delivered. is it because he hasn't opened the skype?
SOURCE: instant messaging not working on skype
If you are sending an instant message to a contact who's offline, then you will see the rotating grey circle. Once that contact goes online, he/she will get your instant message.
However, if both of you are online and your messages still can't get through, try calling your contact Skype to Skype to get the message through. I don't know the exact explanation behind it, but that's what we often do and it works.
SOURCE: IM message in Skype won't
this can only happen due to internet connection issues, check for any firewalls blocking skype
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