Why I switched from Windows Live Messenger to Skype IM and you should too

Up until about four week ago, I used Windows Live Messenger almost exclusively. That was until Windows 8 Consumer Preview’s “Messaging” integration drove me insane with the lack of control on updates and disabling the ability to send group messages on other computers also signed in.

Because I had been more actively using Skype over the past year (after Microsoft bought it), I started using Skype for instant messaging as well. To my surprise, it’s now become my default instant messaging client and here’s just a few reasons why I would recommend others to switch too.

  • Synced chat history across all clients – If you use as many PCs and devices (tablets, phones) as I do, you’ll come to appreciate the fact that chat logs aren’t stored on just one PC like they are with WLM, but they are in the cloud and automatically synced to any of your Skype clients. You can easily take a conversation from a home PC, to a phone and to a work PC without anyone the wiser.
  • Easier group chat/collaboration – Group chats on WLM has never been reliable or predictable for me. Sometimes participants can’t join, other times they fail. In Skype they just work. The initiator can even remove users from conversations which is always handy. File transfers also work in Skype group chats.
  • Screen sharing & voice/video calls – Sometimes it’s just easier and faster to just show or say what you mean. Even though group screen sharing and video calls in Skype costs extra money, the quality is much higher. Voice for the most part has been sufficient for me in group discussions.
  • No annoying ads – There are some ads in Skype, but neither as annoying or as intrusive as the ones in Windows Live Messenger today. I cannot use WLM without A-Patch removing the ads.
  • Better emoticons – Sometimes an emoticon like (hug) is just what it takes to set the mood for an important discussion.
  • No nagging Microsoft SmartScreen messagesOne less step between you and the cute cat pictures your friends want to show you.

26 insightful thoughts

  1. Agreed. I generally have both running but if I have a contact on both I invariably find these days that I’m using Skype.

    Synced chat history is nice. Do you know if there’s a way to search all of your chat history? I’ve always wanted that for WLM.

  2. If only the interface would be cleaner. I especially hate those extra “close” buttons on every single window. Who had this brilliant idea?!

  3. It’s too bad Skype looks like ass. WLM’s aesthetics and cleaner-feeling UI keep it ahead for me.

  4. These are valid reasons. Synchronized chat history is a must have in my opinion. It has some small flaws in Skype (sometimes, messages I read on one device popping up as unread when I sign in on other devices.) but is fine after all.

    There is another option I’m using, the Multi Messenger Trillian. It has synchronized chat history (even some “continuous client” aspects like keeping open chats in sync (if you start a conversation on your phone and log in on your pc it will automatically open the chat on your pc)) and it makes no difference whether you chat with someone that’s using WLM, Facebook, etc.
    The Skype integration in Trillian is not perfect, so I keep using the Skype client when making calls, but it’s enough for chats.

  5. Now that Microsoft is killing the “Windows Live” branding, and since now they have two IM clients (WL Messenger and Skype), maybe they’ll merge the two clients in one.
    Look: Hotmail (for email), SkyDrive (for cloud storage), Skype (for IM and VoIP). Nice, catchy and short names πŸ™‚

    And I agree with everything you said.

  6. I’ll switch away from Messenger the day you can convince all my friends and my entire family to do so as well. Messenger is tremendously popular in the Netherlands (as well as other parts of Europe).

    Skype also has the problem that it doesn’t support high-DPI at all.

  7. Better emoticons? Messenger lets you create any emoticon you like. I have yet to find another IM service with that functionality.

  8. The quality of one to one audio conversations also matters. While I agree Skype has its plus points, so does Live Messenger. I think the same company owning both is a big mistake and the overlap will cause one of them to get killed. Wait till Microsoft haphazardly merges the two, and then new client will be “re-imagined” and “simplified” to the point of being useless like what happened with Messenger morphing into the “Messaging” app. Even if you use the 2011 desktop version, it’s horrible. It used to be a good IM app. The 2009 version is good if you A-Patch it and like I said, Skype does have good group messaging features, but it also has many annoyances. WLM 2009 isn’t so bad if don’t do group audio or IMs. And I certainly don’t want my chat history sent over the cloud to be synced! Otherwise, I would use Facebook chat. The main problem I have with Skype is that the audio call quality isn’t good as Messenger, it’s too synthetic sounding for me (remember it can vary from your experience) and Skype is annoyware. In Messenger for example, 1 button starts two-way video. It’s a lot more clicks in Skype. I hate the day when the two would be merged. I hope they are never merged and MS has the sense to keep both alternatives.

  9. Personally, I like Yahoo Messenger the most. It is the most efficient with the use of space in the chat window, and I think the emoticons are by far the best–they have the best focus on the purpose of emoticons: expressing emotion that might be missed using words alone. WLM’s emoticons aren’t great (lots of extraneous stuff like a goat, bunny, sheep, chopsticks, etc.; Yahoo has a few of these as well, but far more emotion-based ones, and much better drawn), but at least it allows the ability to import images for use as emoticons (I import Yahoo’s set). Skype’s emoticons are even worse than WLM’s, and there’s no import ability. I also miss the ability to draw images in WLM (why’d they drop it?), and I prefer WLM’s photo-sharing function to Skype. Yahoo allows in-line text formatting, WLM allows font changes per sent message, but Skype allows neither.

    I think Skype’s UI is the worst of the three. I also don’t understand the way the personal photo function works. It shows a magnifying glass to “maximize” the image, but the image itself doesn’t get any bigger–it just gets a bigger border. I do like the synchronized history, and it works pretty well except when you login to another computer–you start getting a bunch of pop-ups for all the messages you’ve sent from another machine (rather bizarre behavior). Yahoo has this as well, although it seems to be glitchy. In particular, I’ve never been able to import my old conversations (back when it was stored locally)–I’ve contacted support, and received no response. There have also been a couple occasions where it was unable to pull up the history, but a later attempt was successful. However, WLM is the worst offender here–it doesn’t save on-the-fly. Unless you close the conversation, the history is not kept. If WLM crashes or if your computer reboots after an automatic update, you lose the history of all your open conversations. If someone sent you a message while you were away, there’s no way for you to know. Yahoo allows you to see all conversation histories in one view, sorted by date, which easily lets you determine if you missed any messages.

    They all have some good points, but overall, I think Yahoo Messenger easily beats both Skype and WLM.

  10. I have two additional annoyances regarding WLM (2011):
    – The taskbar icon remaining orange even after selecting the window with the new message (selecting it again fixes it). I think by adding support for tabbed conversations they made the experience worse for those of us who prefer to have separate windows, as this wasn’t an issue in previous versions.
    – When I receive messages from a certain contact, the new window steals focus, even from full-screen programs. Fortunately this happens only for one person, otherwise I would have abandoned WLM entirely long ago.

    I sure hope Microsoft doesn’t decide to add SmartScreen to Skype. I wrote a Greasemonkey script to automatically skip the warning page, but they periodically update the URL format which breaks my script. It would be much easier if there were an official option to disable it.

    I’m not a fan of the custom window frame that Skype uses, but at least it’s possible to switch to the standard appearance.

  11. I use Skype for IM as well. What I like most about it is the conversation syncing, just like what you get with Apple iMessage. But, instead of only running on OS X, I have Skype clients set up on my Windows desktop, my Windows Phone, our family iPad and my wife’s iPhone. We can talk throughout the day (we have three kids, so it’s essential for organizing ourselves) for free. Skype is pretty awesome.

  12. I would but since all of my contacts are on Windows Live Messenger, and I would have to create another account for skype, I will not do this. Unless Skype allows me to log in with my Live ID, and show all my Windows Live contacts, I most likly wil not be using skype. I also do not like the messenger app in Win8, reason why I installed Windows Live Essentials 2011

  13. “Chat logs aren’t stored on just one PC like they are with WLM, but they are in the cloud and automatically synced to any of your Skype clients. You can easily take a conversation from a home PC, to a phone and to a work PC without anyone the wiser.”

    Chat logs are not in the cloud. That would be a great feature (the paid version of Skype-connectable Trillian offers it, however). No, instead, Skype clients merely sync recent messages when the “other” Skype is also online. It’s only the last couple weeks’ worth at most, it’s unpredictable (it rarely happens when you need it to), and at times it’s annoying (it often happens when you don’t want it to, popping up notices of old messages that it should have synced earlier), but it sort of works (barely).

    One thing that Messenger has and Skype HAD (before a massive outage in late 2010 was connected with it) is offline messaging. That is, the ability to send a message to someone who’s offline and expect them to receive it even if you go offline after sending the message. Sadly, ever since late 2010, both parties need to be online for a message to be received. I’ve been hoping that MS would reinstate the feature, particularly now that we’re hearing that they’re apparently killing Skype P2P and instead are building more servers (it was the servers that were apparently overwhelmed in late 2010), but nothing so far.

  14. I’d consider using Skype again if they’ve finally addressed the home-screen-keeps-redisplaying-itself-and-advertising feature they had a year ago.

    1. How old a version of Skype are you running? They fixed that problem in later September!

  15. You forget to mention that the Skype UI is just about the worst UI on any application, on any platform, ever. I sometimes spend time clicking around just wondering to myself what the hell the developers were thinking.

  16. Long, are you feeling OK? It’s just that it is so unlike you to dump a Microsoft product in favour of a non-Microsoft product!

  17. We moved all business communication over to Skype a while ago – IM (nternal and external), conference calls, oubound calls – it replaces Messenger, Lync and the phone system in one, They just need a kick in hte UI pants it’s a mess.

  18. Guys i do not see the WLM contacts untill i will choose in the start screen option to log by the Microsoft Account. If i log in by skype ID i do not see WLM contacts… is this normal behaviour?

    1. Yes, it working as intended. They want to force (or gently direct) people to merge the Live ID and Skype accounts.
      But if you do, you still will be able to use Skype ID if you want. Or at least when i merged mine it said so. πŸ™‚


    This is nothing more than corporate bullshit with companies forcing their products down out throat. If I wanted to use Skype I would have used it to begin with, not Windows Live. Theres plenty Windows Live has that Skye doesn’t such as nice starting emotes, the ability to use custom emotes, stability (after I updated to Skype it crashed nonstop),You can no longer see your own display picture (alot of people enjoyed this feature then Skype decides to remove it from all but the edit menu), and alot of other stuff. In this case the losses far outweigh the gains.

  20. its funny the majority of these posts talking about the “good” features of what skype has and others dont, all say the same about the chat logs…or the one about yahoo wow im surprised ANYONE likes yahoo messenger its so bogged down with adds all over the place, and about the emoticons…its pretty apparent all these people havent heard of or tried trillian, everything everyones been talking about of good in each of the different services from yahoo, skype to gmail and facebook are ALL in trillian. you can even pick your own emotes and download packages for custom ones, you can completely personalize your buddylist window and chat windows with tons of different themes, i have a mario bros one, set it up with its own sounds to match even. can even make it go transparent when not in focus. all the chat logs are saved on my comp and even when switching to a new comp or my phone the conversations are all updated to it.

    if your friends had msn accounts you dont even need to fuss with that, you never even have to worry which messenger service your replying back to or from its all automated from trillian, if they have multiple accounts you can even stack them all in one and choose which you want to message by default or right click and pick yourself. its totally light weight too trillian running takes about 28k memory, skype 113k…

    and yes the skype UI omg that thing xD WHY is the window so *&^%#ing biiig! of course the OP posted a pic of it on a phone…yeh corporate bs seems so too mee too, along with a few of the other posts hahahah

    if you use a mac, and everyone really should πŸ˜‰ adium is an amazing alternative to trillian, had i the monies to buy a mac with as much power as my current windows has for the price i paid for it i would totally have but until i can convert it to a hackintosh trillian is an awesome program faaaaar superior to the others, aside from adium πŸ˜› my favorite feature with that is being able to make windows that are still in focus as transparent as i want, watching a movie or show on here full screen i can still alt tab to my chat and talk while still watching the show, and see my text and theirs clearly enough without hassle πŸ™‚ trillain only does it for ones out of focus but its still more than most do πŸ˜›

Comments are closed.