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I have Live Messenger version 2009 Build 14.0.8117.416, on Windows XP SP3.

I have a wireless USB modem which connects to the Internet before Live Messenger finishes loading.

Under Tools > Options > Sign In, Allow automatic login when signed into the Internet is checked.

It will sign in manually, but why not automatically?

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At the login screen, have you checked "Sign me in automatically"? It should be available after clicking the down arrow at the bottom right of the box where the userdetails fields are. (Not visible on screenshot, it is omitted when no details are saved yet.)

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Yes, I believe so, and I will confirm this when I get home. – Steve Jan 17 '11 at 8:52
Duh. You were right, thanks. Not sure why there is the setting Under Tools > Options > Sign In, Allow automatic login when signed into the Internet. – Steve Jan 17 '11 at 10:41
@Steve You're welcome. And that options only Allows to sign in automatically, it doesn't say it Will. – BloodPhilia Jan 17 '11 at 10:58
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