Skype Community threads attesting to this problem To test this: restart Skype, and if your contact is now showing up as offline, then that was the problem: messages are not marked as delivered until both of you are online simultaneously (at least, this was the case when I first wrote this article back in 2014 - the situation may be different now that Skype stores messages on its servers). Another possibility: your contact is offlineĪnother possibility is that your contact is actually offline, even though s/he is showing up as online: sometimes, Skype doesn't "realise" that someone in your contacts list has gone offline. You can check the Skype Status page, amongst others, to find out whether there's an outage affecting you. In that case, the workarounds on this page will be futile, and all you can do is wait until the Skype technicians solve the problem.
Another possibility: your contact is offline.First up: check that the problem is not a server outage.Unfortunately, it does not provide a perfectly simple, reliable, universal, and risk-free workaround, although the first one comes close.
Whilst only the Skype developers can provide a permanent solution to this problem, this page attempts to offer potential workarounds. Sometimes, the messages remain blocked - inexplicably - for hours or even days. Sometimes, in an instant messaging conversation on Skype, messages are marked as "pending" for no apparent reason: neither chat partner has blocked the other, and both are online.
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How to fix inexplicably undelivered/pending/blocked Skype messages
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