7 Skype Bugs That Microsoft Could Have Avoided

Mark O'Neill 29-01-2016

When Microsoft bought Skype back in 2011, a collective groan could be heard around the Internet. A beautifully made product, constructed by a dedicated team from Sweden, Denmark, and Estonia, was now being taken over by the Redmond giant; the same beast that tried to force the worst browser ever 8 Most Common Internet Explorer Issues (And Easy Ways to Fix Them) Here are some of the most common problems you may encounter with IE and quick and easy solutions for fixing them. Read More  on us.


The seeds for the total meltdown of Skype were born. The transition has been bumpy, but certainly smoother than expected. With the latest Skype update, it looked as if the world’s most well-known VOIP was stuttering once again.

What Was the Problem?

1. Chat Messages Out of Order

After the Skype update to version, when two people were having an instant chat conversation on the Windows desktop version of Skype, the messages would appear out of order. Seeing the messages of a long conversation all over the place would get annoying really quickly.


But what is really strange is that if you then closed the chat window and reopened it, the messages would be back in their correct order.

2. Stubborn Unread Messages

The second problem was that read messages were staying marked as unread, despite clicking on them several times. This meant that the bouncing number on the Skype icon which indicates how many read messages you have, refused to clear (as well as the dots that sit in every unread chat message).



The only way to mark them as read was to go to the Skype contact list, right-click on the contact’s name, and choose “Mark Conversation as Read”. Moreover, clicking this menu option didn’t do anything the first time around; the messages only became unread after clicking the menu option 2 or 3 times. For someone having many or drawn-out conversations, this would become very tedious very fast.

The Skype forums quickly filled up with angry users describing the problem and demanding that Skype do something. But what was Microsoft/Skype’s solution to the problem? Was it to work around the clock on very little sleep and lots of caffeine to find a patch, while listening to “Eye Of The Tiger” for inspiration? No, not exactly. Their solution swas for users “to downgrade” to the previous version until they could figure out what was going on.

The new patch finally came out, and apart from one or two blips, it seems to be holding so far. But the advice to downgrade? That was a bit embarrassing Microsoft.



Steady Skype Issues

Right now you’re probably thinking “OK, they screwed up, happens to the best of us, it’s fixed now. So what’s the big deal?” Well the big deal is that this is not an isolated incident.

Since Microsoft took over Skype 5 years ago, we have had one technical SNAFU after the other. Which is bad because everyone has Skype in their lives so much that when it goes down, everyone plunges into mourning. It’s the same when Facebook goes down – “Facebook is DOWN! What will we DO now? What Do You Do When Facebook Is Down? [MakeUseOf Poll] Facebook is one of the cornerstones of the Internet, and five minutes of downtime can cause mayhem. And panic. And mass hysteria. So, what do you do when Facebook goes down? Read More “.

Skype is used for keeping in touch with loved ones, but it is also used by people in companies, and self-employed workers. When Skype sneezes, it’s the users who hold the collective tissue to sneeze, too. I rely on Skype for my business. So do tens of millions of other people.


3. Messages Are not Syncing Instantly Between Devices

You will constantly experience this problem if you use multiple devices, and especially if you use different platforms. For example, I use Skype on a Windows PC, a Macbook, an iPad, and an iPhone (and it always stays open). So I am constantly starting a conversation on one, and continuing it on another. You would assume that the messages would update on each device instantly. You would assume wrong.


If I stop an instant messaging conversation on my MacBook and move to my iPhone, because I need to run out the door, the last message sent is not there. Neither are the 5 before that. Or even the 5 before that. For me, it can take up to 10 minutes for the apps to sync. If you are discussing a time-sensitive article with a client, or negotiating a work contract with someone How To Win A Job Interview Via Skype For some reason, many tech users tend to separate "reality" from what's on their computer screen. We're bolder people online, hiding behind text conversations, artsy profile pictures, and creative (and also sometimes off-color) user names.... Read More , those 10 minutes can make all the difference.

This is not an issue with Apple alone; my wife has reported the same issues with her Windows PC and her Android phone.


4. Transferring Files Drives You Nuts

It was meant to be an easy task. Scan an important time-sensitive letter and send it to a relative in the UK. A single sheet of paper, in black and white (I made a black and white copy to strip all the color out). You would think it would go through immediately. No Monsieur. Skype went off for a coffee break, while it decided whether or not to help me out.

Skype File Transfer

File transfers work a lot of the time The Fastest File Transfer Methods Between PCs and Mobile Devices PC-to-mobile files transfers are easy to do. This article covers five fast transfer methods between PCs and mobile devices. Read More , but “a lot of the time” by its very definition means you can’t rely on it 100%. The times when it chooses to be awkward are usually the times when you need it the most. It’s those times when the fastest way to deliver the document to its intended recipient is to swim the ocean, jump on the donkey, and deliver it yourself.

5. Messages Are Delivered Hours Later

This is an extension of the messages not syncing problem. When one person sends a message, it is automatically assumed that the recipient at the other end receives the message either immediately, or a few seconds later.


But there have been frequent occasions when the message is held by Skype and then delivered several hours later. In one case, I received a message a day later, resulting in a very serious misunderstanding. Meanwhile, the other person is wondering why you are not responding.

Then when the message finally DOES arrive, it often is not slotted into its correct position in the conversation, making interpreting the situation rather difficult. It’s around this point, in between head-butting your desk and wailing in a dozen ancient languages, that you begin to question Skype’s usefulness for work purposes.

6. Group Chat Is Shaky at Best

Group chat 10 Tips To Get Most Out Of Skype Video Conferences With the right setup, Skype can be a great tool for private or professional video conferences. Video chat requires quite significant resources from your computer. This article will walk you through the basic preparations that... Read More sounds like a great concept. Let’s all get together in a virtual Skype room, and either instant message one another or video call. People from different geographical locations can come together and we can all pretend to be in the same room as one another. Yeeaahhh…..right. Nice concept, bad execution.

The main issue here is dropped calls. Either the entire call, or some poor soul gets kicked off. Then there’s people unable to hear what others are saying, and a noticeable time lag in video feeds. And before you blame the person’s Internet connection, these are people with high speed connections. But Skype acts as if they are on a 56k modem.

7. The Big Skype Outage of September 2015

Anyone that heavily relies on Skype will no doubt remember the big outage of September 2015, when the network went down for over a day, and the entire online world acted as if the end of the world was coming.

Companies ground to a halt, geeks could no longer communicate with other geeks during World of Warcraft Getting Started With World Of Warcraft: A Complete Newbie’s Guide Here’s what you need to know if you’ve never tried World of Warcraft before. Read More , and the Nigerian princes Do Nigerian Scam Emails Hide A Terrible Secret? [Opinion] Another day, another spam email drops into my inbox, somehow working its way around the Windows Live spam filter that does such a good job of protecting my eyes from all of the other unsolicited... Read More looking to move their $50 billion couldn’t send you Skype messages asking if they could trust you with “a most momentous task”.

The problem? “Network issues”. Or to be more specific,

We released a larger-than-usual configuration change, which some versions of Skype were unable to process correctly therefore disconnecting users from the network.

When these users tried to reconnect, heavy traffic was created and some of you were unable to use Skype’s free services, including messaging, presence and contact list management. Others could not sign in or out of Skype altogether, or make calls to landlines or mobile phones. Skype for Business was not impacted.

Well hey, as long as the paying customers didn’t have to suffer.

Why Oh Why the Pain?

All of this leads to a single question: Why is the Windows desktop version of Skype suffering so much?

Since Microsoft killed the Windows 8 app in favor of the desktop app last year, you would think that the desktop app would be getting lots of love. But it is one too many hiccups for my liking.

True, the translator app has been a HUGE success Skype Translator Offers Live Interpretation in up to 50 Languages - Free Preview Now Open to All Everyone wants to speak a foreign language, but few are up to learning one. Skype Translator can help you interpret up to 50 written languages, including Klingon and spoken Spanish. Here's how to use it. Read More . I have it on my Skype app and I use it sometimes with clients who have dodgy English. So it’s not ALL been bad. But when you consider the points above, one good thing does not balance out the rest.


And Microsoft really needs to get its act together, as it is starting to face stiff competition 6 Open Source Messaging Apps More Secure Than Skype Skype has never been the most safe or secure communication protocol, and after Microsoft took over in 2011, concerns over privacy began to pile up. Can these secure, open source alternatives allay those fears? Read More in the VOIP/instant messaging arena. Consider some of the contenders – WhatsApp, Viber, Signal, Telegram, Facebook Messenger, and iMessages. More will come out of the woodwork, as surely as night follows day.

Microsoft was not available to comment.

What Are Your Feelings About Skype? Are you experiencing these same issues? Do you think Skype’s technical snafus is causing it to lose ground to rivals such as WhatsApp? Let us know your opinions in the comments.

Image credits: Skype on phone by Twin Design via Shutterstock, attribution-free images courtesy of PixaBay

Related topics: Microsoft, Skype.

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  1. Rob Ward
    January 10, 2018 at 3:36 pm

    Skype update, that i didnt ask for, now means the other speaker cant hear me.... why oh why?
    and of course there is no one to call, etc.. how can i resolve this?

  2. za
    November 14, 2016 at 2:40 pm

    Skype suck !

  3. David
    May 31, 2016 at 6:30 pm

    It's only a small thing but it bugs me that I now have to sign back in to Skype every time it gets updated.

    • Mark O'Neill
      June 1, 2016 at 1:17 pm

      You're right. I never really thought about it all that much. But now that you mention it, it IS a pain in the rear having to constantly sign in again....

  4. Doc
    January 31, 2016 at 4:23 am

    Newest glitch: People on my boss's address list get spam messages with a "" link to (possibly infected) pages pushing a weight-loss product.

    • Mark O'Neill
      June 1, 2016 at 1:18 pm

      That sounds like you have a virus on your computer. Or someone has gained access to your Skype account. Start virus scanning and change your Skype password.

      • Anonymous
        June 1, 2016 at 10:05 pm

        Turns out it was crappy security on Microsoft's part; in a couple of days, they sorted it out, and the spam stopped. All of the company's computers are secured with Webroot or Avast, with Malwarebytes as a "second opinion." They're clean.

  5. Fik of borg
    January 30, 2016 at 12:58 pm

    That's what one would think, but bugs and all, Skype is way easier to use for my elderly relatives than the more elegant Hangouts ... which let's face it: is a pain in the coccyx to set up (it's video chat. there is nothing to set up in it's text chat).
    And mobile Hangouts is sloooow: I have tried to chat with one account from my PC to another account in my phone and sometimes it might as well have not send the message.

  6. Frank John
    January 29, 2016 at 4:15 pm

    Skype cannot hold a torch to Google Hangouts.
    One needs to abandon Skype and adopt Hangouts.

    • Mark O'Neill
      January 29, 2016 at 10:14 pm

      What makes Hangouts more superior in your opinion?

      • vog
        July 26, 2017 at 3:01 am

        I have not tried Hangouts yet. But Skype has long stopped to work on my desktop and laptop (both Windows 7) I have to look somewhere else, in stead of just cursing. I still have some 40 dollars (Canadian) credit with Skype. How could a power house software company like Microsoft fail so badly? And why do they want to turn off their users?