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My account started off as Hotmail, now it is Outlook. It takes me to three different places to sign in before it will allow me to even see my emails.

How can I shorten that to the normal one click sign in?

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    What address (URL) are you using to sign-in? – Rubén Nov 27 '17 at 3:07
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I use https://outlook.live.com/mail/#/inbox as my bookmark for hotmail/outlook. If I'm not logged in I get taken to a page to put in my @hotmail.com email, and if I am I get taken directly to my mailbox.

Outlook is now what Microsoft mail is called globally. Hotmail accounts still work, they just don't use hotmail's branding anymore for their products.

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