Shoutbox

I'll quote myself from a previous post elsewhere. I did change things here and there though, but it fits the situation perfectly:

File Transfers
They are slow compared to other applications. The transfers are limited (under normal circumstances) to three at a time. What for? No browser limits me to that, why should my instant messenger do it? The progress bar isn't as detailed as one would expect (perhaps an estimated time remaining, like most people have come to be accustomed with other programs?).

Invite feature?
Sorry to break it to you Microsoft, but that's not an invite button at all. That's a "force this contact into this conversation" button. This means that your email can get revealed to someone you may not want, you may be forced into a conversation with way too many people, perhaps even people you have blocked. Instead of labelling it invite, if you're not going to make a proper invite feature, why not label it "Force a contact to join this conversation"?

Customization
Although this has improved lately with the new "Layout" tab in the options, Windows Live Messenger doesn't have half as much customization from the base product as it should. Users requested skinning for so long, why is it that Patchou had to be the one to add it in? They say they listen to user feedback, yet the closest step they have taken to skinning in all the years is probably backgrounds in conversation windows, and the new scenes. On that note, it seems that you can't have a scene that fits everyone, many contacts will see it distorted in some way.

Forced updates
What's with that? Forcing users to update, otherwise they can't use the application? Sure, it might fix an exploit, and in that case it's understandable. But otherwise? Why would you force users to update if it's not to actually make it safer? At least give them the choice to update right away or not. It's their computer after all.

The contact list
Why can we not order the contacts in any way we want? It's possible now with the favourite group, but other than that, it's alphabetical or online versus offline, and that's it. What if I want certain contacts to be at the top all the time, regardless? Drag and drop should work every time, for whatever I want to do.

Tabbed chats?
Sure, Messenger Plus! does it, and quite great. It would suck to steal from Messenger Plus!, but if they listened to users' feedback over the years, Messenger Plus! would not have had to implement it. Users have requested it forever, and never got it. Of course they'll turn to another application to do it, but should they have to?

Formatting
Don't get me wrong, I love using stuff like Messenger Plus!, and I can tolerate using it for stuff like tabs and all that, because that may not be a feature that everyone wants, but formatting should definitely be implemented directly. The one thing that's useful in conversations is adding bold or italics to emphasize something. Maybe not colours, but at least a way to change the formatting in the middle of a sentence or paragraph. Now I can do it, but only with people that have Messenger Plus! installed as well. What a loss...

Custom emoticons
I love the idea of being able to have custom emoticons, but I hate the idea of people being able to abuse it. I don't want to turn them all off for those few contacts that abuse it. I should be able to set it so only certain contacts can't send me custom emoticons, it should be simple enough.

Polygamy
Why is that not implemented directly? I just don't get it. Thanks again Messenger Plus! (and not to mention Mess Patch and A-patch and also Messenger Discovery).

Custom Statuses
That is implemented in most other IM programs, why not this one? Especially now with brb gone, I don't want to set my status to away only for a minute or two, yet I want people that decide to start a conversation to be aware that I won't reply right away. It'd be nice to have custom statuses. Thanks Plus!

Connection/servers
Sure, it's normal that servers have maintenance and things need to be upgraded and kept well. Why not connect me to a backup server, or a server from another country that while a little bit slower may allow me to still connect? Just because my account is assigned a specific server, when it's down, I shouldn't have to be down with it. There are usually other servers that are up and running, spread the load but keep it active.