The Skype debacle: What's happening to my messages?

When Microsoft announced that Skype would become the company's premier messaging service and that MSN/Live messenger would be replaced with it, the logic behind the move made a lot of sense as it had two messaging platforms and merging them into one service would be easier to maintain. What was more surprising too, was how quickly Microsoft was planning to discontinue the MSN platform as the company has traditionally been quite slow to phase out products. 

While we love the new cadence that Microsoft has been showing with rapid updates and increased refresh rates for key services, the Skype/MSN service merger has not been without issue and it's causing me to lose faith that the platform is hitting primetime starting April 8th.

Here is the issue that has been plaguing me and many others who use both MSN and Skype: messages from MSN to Skype users are getting lost, well, not lost as in they are never seen again, but lost in transmission and they take a loop around the arctic circle before arriving at their destination. For example, I chat frequently with our lead designer, @timan25, on MSN/Skype. I am on Skype, he is on MSN, and our messages have frequently arrived so late, that it's typically the next day before he is even aware that I responded to a question.

This is not an isolated incident, I have had issues talking with @maryjofoley on Skype/MSN (she uses Trillian for messaging) where she will send messages to me and they will not arrive for several hours. One incident occurred yesterday where her messages were showing up on my Skype iOS client but not on my desktop (Windows 8) client. The messages eventually made their way to my Windows 8 client after nearly four hours of waiting.

Now, the delay does not happen all the time but it happens frequently enough that my confidence in the platform is beginning to waver. There are other issues as well when you merge your MSN account with Skype such as contact duplication but those are only minor annoyances for those who had the same contacts on MSN and Skype.

Additionally, it is quite frequent that messages will arrive out of order as well. This has happened frequently when using an old conversation that you still had open and then trying to engage in a new conversation, the messages will be sporadic and out of order.

The bigger issue here is what is happening to these delayed messages. All of the other issues with the merger have not provided any functional decline in the use of the communication tool, but this message delay bug is making it difficult to trust the platform. I am not alone with this issue as a quick search on Google pulls up hundreds of results for the same problem.

One of the results of the delayed messages is that if you get quite a few lost in space, when your client does sync back up, you get bombarded with messages, sometimes in the middle of the night. A few weeks back I had 100+ messages sync to my phone while sleeping. As you can imagine, when your phone gets bombarded by over 100 messages, it makes quite a racket while sitting on my nightstand and makes for an unwelcome disturbance in the middle of the night. 

With the full transition starting April 8th (minus the API discontinuation which will happen in the near future) and the delayed message issue still heavily persistent, we begin to question if the product is actually ready for the transition.

We hope that Microsoft can resolve the issues quickly as I love Skype and use it every day to communicate with friends and co-workers but until the delayed message issue is corrected, it becomes an unknown variable if the person you are trying to communicate with will receive your messages.

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I've seen similar, but shorter, delays when messaging Facebook contacts from Skype too.

Seriously, it's a communication tool. The technology has been around for years. It has one simple job to do, and it can't do that right.

I dumped it in favour of Trillian.

Facebook messages get stupid delays too, and sometimes only half the conversation shows in Skype. Also as someone else said, having multiple Skype clients open can really confuse Skype =P
Bit awkward when I leave it logged in at work, on my desktop, on my desktop as a windows 8 app, and on my laptop, and on my phone.
Bit confusing too when you get the message to half those platforms and not the rest...Wut =P

They really just need to add an option to disable messaging in the Skype apps. Now, every time I use Skype I start getting duplicate messages from what used to be the Live Messenger service. The most annoying part is that you can't stop it on Windows 8/RT without uninstalling Skype.

This bug has existed for years. It's not just with Skype. It can also sometimes take me forever to receive messages from Facebook.

I'm sure this will clear up after they transition everyone. After all they're merging two huge IM networks into one which is no easy job to do...

I'm sure the backend transition has been done for a long, long time. They're only killing the ability to logon with Messenger. Not like they're wrapping everything up the day they go live with that.

Not shocking. I always found Skype to be completely crap for IMing, messages frequently got lost or held up. Hopefully Microsoft will iron out the kinks (which they should have done before axing live messenger IMO)

I'm not amused they're shutting down WLM either. I'm using both atm, and most of my WLM contacts just aren't showing in Skype. That renders it totally useless...

If I'm reading this correctly, this isn't people with updated WLM accounts to Skype accounts but people who have their WLM accounts merged with Skype and still message to people on WLM. If so, wouldn't that go away when it's all on Skype? I can understand your current frustration but it's not like people are going to be able to use WLM since the service itself is going down.

Zedox said,
If I'm reading this correctly, this isn't people with updated WLM accounts to Skype accounts but people who have their WLM accounts merged with Skype and still message to people on WLM. If so, wouldn't that go away when it's all on Skype? I can understand your current frustration but it's not like people are going to be able to use WLM since the service itself is going down.
Agreed, my skype to skype communication has been as perfect as always throughout the transition.

This is frequently happening to me as well, but only when I have two clients logged on at the same time. Seems to confuse the Skype service.

Microsoft are absolutely stupid for getting rid of WLM. It was my childhood. The best messgaing app ever. Seriously man, someone find out who's decision it was to remove WLM and get me in a boxing ring with the guy. Anyone who can sponsor this please do so. Typing on Skype feels like my soul doesn't connect with the person I'm chatting to. IT'S LIKE TYPING TO SOMEONE FROM ANOTHER PLANET. FFS.


An editorial still referring to Windows Live Messenger as MSN ... very poor. That branding for Messenger
was axed 7 years ago. MSN is a content portal ever since then, and it isn't being replaced by Skype.

Though technically incorrect, WLM was still wildly referred to as "MSN" which actually shows the power of the MSN brand as an IM product (but no so much as a portal which is awful...just awful).

Wish they would just send Skype & Messenger to the great recycle bin in the sky and replace both with an ad supported Lync 2013 service.

no. that's not what he was suggesting.
Both WLM and Skype are inferior to Lync 2013 - all three are Microsoft products, and all tick similar boxes. Moving from 3 platforms to 2 doesn't make as much sense as moving from 3 to 1.

correct me if I am wrong but its Skype uses P2P connection with servers as a back up and the issues is the sync not working or often enough and that's the problem.

Neobond said,
Yeah the Windows 8 messaging app is very poor compared to WLM.

I think calling the Windows 8 messaging app poor is abuse of the word poor. It's a little more then an annoyance for most people. The Skype app is little better, but it boggles the mind as to why Microsoft hasn't updated the included messaging app with Skype app.
I understand the messaging app is supposed to be a hub app, but it can't even do the most basic of things like send and receive messages let alone any thing complex like send a simple file.

And that gets me on to the Skype app. It's only recently that they've added send file function there. For regular users of Windows Live Messenger, sending files might not have been a biggie, but the share picture function was and that is sorely missed. Yet, Windows 8 is more then the perfect platform for it. Share charms menu from the Picture library? nope not to Skype, and it just feels like the entire app system they're trying to build is half-baked after thought that they don't really have an interest in. Even my Windows Phone could send files!

As for the problems about messages being delayed.. I've been commenting it for a several months now and I've tried everything to fix it, from linking and unlink my Skype/Microsoft accounts (that is limited to a number of times too!!, wth) to using Skype desktop, or Skype app only, to removing them both and trying to get by with the messages app, I even tried to use the webmail's chat function, and even turned my Windows Phone off for a week!
Gone are the old error messages about 'we're almost ready' or 'your chat partner is having problems receiving your message' etc, you simply don't know if they're getting the message anymore.

Twice now, I've had over 50 messages from different people flood into me all at once, delayed for a month! That's not an IM program, that's not even email. I could have written a letter and and hand delivered it faster then that.
I've reported it to Microsoft on their forums a number of times, but it feels like now they have no core testers there isn't a real way to send proper information to them that they'll accept as important and not just a user error.

It's gotten to the point now, where the Apps are so poor I've stopped using them, that's it. I like Windows 8 but the apps as good as they could have made them has let it down big time. I've even contemplated getting a Mac again, the only thing stopping me is my game collection on Steam (ironically).

WLM had problem with offline users, I was not able to send a message to those who were offline. Now that everything is connected, that problem persist. The servers get confused when you are using multiple devices. It's annoying.