Recently, we encountered several issues with Skype chat, which made it nearly impossible to provide proper support via this channel.
The first issue we experienced several times (i.e. daily) was that Skype popped up the incoming messages only days later they were sent to us. I checked this on the Skype forums, and found out that Skype handles offline messages in a very weird way: let’s say a customer tries to contact us at 11:00 PM CET (surprisingly, we are not in the office at 11PM :). As we are offline the message is not delivered. Next morning, we start up the engines including Skype, we are online. You would expect that it notifies me that “Hey! Somebody tried to send you an urgent message! He even left his email address so you can contact him immediately!” But no!
Skype delivers the message only when both the customer and us are online! Which means: in most cases, never. Or days, even weeks later.

If you think about it, you can say: “OK, that is reasonable in some way, as we can contact each other via Skype only if both of us are online”. But there are other means of communication as well, that’s what Skype fails to understand.
Moreover, we had several cases when I received an old message from a time period when I was definitely online. In other cases, the customer sent us a message, I received it immediately, we were both online, but I could not answer (I received “Your message is not yet delivered” errors).

How do you explain these? I checked the Skype forums again, others have the same issues (so it’s not just me). Skype replied with the million-dollar solution: update to the latest version. But we already have the latest version… Then they told us this problem may occur if I have a different Skype version from the people I’m trying to talk to. Whaaaaat? So in order to send messages to each other, both of us should be online and both of us should have the same (latest) version. This is nearly impossible, but let’s say we managed to achieve it. Even then, Skype drops the connections randomly.
Imagine this reliability in a product environment, for example if we would decide to provide support via Skype only to save money…
Now I’m not surprised anymore when I get messages like this once in a while:

Me, too, buddy. Me, too…