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No more winks, nudges, or shoddy modem connections cutting into your emoticon battles with your best friend (everyone did that, right?): Microsoft's MSN Messenger will officially be signing off Oct. 31.

Microsoft, which had been shifting users of the instant messenger over to Skype since April 2013, kept Messenger alive in China. There, it still dominated the chatting landscape, until more and more messaging competitors crowded the Chinese playing field (i.e. WeChat, WhatsApp). After a year of struggling to retain users, Microsoft finally sent emails this week to its remaining Messenger devotees to announce the closing of the service.

It's the end of a messaging era. To commemorate its 15 years of service, we've outlined the service's changes over the years using its original emoticon package:

1999: MSN Messenger hits desktops, competing against AOL's AIM service. It didn't do much — you could do plain text messaging and create a contact list.

2001: Windows XP (R.I.P.), debuts. Version 4.6 of MSN Messenger appears, including grouping contacts and voice conversations.

2003: Messenger becomes customizable, with personalized avatars, background, and emoticons. Oh, and you could change the theme color.

2005: Winks (giant animated emoticons that annoyingly took up your screen) are added. MSN Messenger is rebranded "Windows Live Messenger."

2006-2007: Audio and video PC-to-phone calling capabilities are introduced, helping the service catch up to Skype, which had been released in 2003.

2008: The "Groups" feature is added for users to create group conversations. New status icons debut. Windows Vista dominates.

2010: Microsoft attempts to make Messenger more social, adding a "social pane" that presented updates from contacts. It wasn't popular.

2012: Microsoft announces merging of Messenger and Skype services and moving clients over to the latter.

2013: Users outside of China lose the service.

2014: Messenger dies. C u l8r, MSN Messenger.

This article is from the archive of our partner The Wire.

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