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Signing it to Outlook.com e-mail

Three part question: I have an Outlook e-mail icon on my taskbar.  When I open my e-mail with that icon, and send a .jpeg attachment, the .jpeg is often converted to a .doc, which many of my contacts (including me) cannot open.  I've tried changing the settings per instructions on the internet and in Outlook.  Nothing works, the .jpegs are still converted to .doc.  How to get rid of the very annoying .doc switch?  If I go to Google Chrome and open my e-mail account, the .jpeg attachments are NOT converted to .doc.  What the heck?  Recently, the log-in address on Google went away (best I can describe it).  Now Outlook insists that I sign up for 365.  I see no need to or advantage in doing so and don't want to.  I finally caved and signed up, just so I could send e-mails that wouldn't convert images to .doc.  It appears that 365 forced me to use a new user name because "someone else is using that name."  Of course someone else is using the name - ME!  But I can't find me.  It also appears that the new account is using a new e-mail address it assigned to me.  When I open the account, the new address appears, but none of my e-mail history appears.  Do I really have to have a new address and notify all my contacts?  What the heck?
Hello -

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Do I really have to have a new address and notify all my contacts? What the heck?
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No, probably not. We need to figure out what happened to your account though.


>> I have an Outlook e-mail icon on my taskbar.
Is this opening Outlook desktop software or outlook in a web browser? Is the file extension really .doc or is it ,dat? As in winmail.dat?


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Recently, the log-in address on Google went away (best I can describe it). Now Outlook insists that I sign up for 365.
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Were you using your gmail address to sign into Outlook.com? What happens when you try to sign in using your old username?
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Diane Poremsky
M365 MVP, specializing in Outlook, Exchange, and Microsoft 365 apps.

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Wow!  Thanks for the quick reply.  I don't know what I was thinking when I typed in .doc.  The system converts the .jpeg files to .dat.  I've been to so many "help" addresses that I can't remember where I found "settings" for Outlook e-mail.  I think the choices regarding .dat were HTML and Plain Text.  Neither setting made .dat go away.  If I understand the system (I'm an old dog with very few tricks), my Task Bar icon opens desktop software.  I'm not aware of a gmail address, only @outlook.com.  I just tried Outlook.com again.  Typed in Outlook and Outlook.live.com/mail popped up - haven't seen that before.  I clicked on it and went right to my e-mail.  Apparently my "proper" user name is still in effect.  But why couldn't I get by the 365 sign-up demand to find my e-mail?

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For winmail.dat files, see https://www.slipstick.com/problems/outlook-is-s... - one option for outlook desktop software is setting a registry key so you never send anything using RTF.

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Apparently my "proper" user name is still in effect. But why couldn't I get by the 365 sign-up demand to find my e-mail?
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Can you post a screenshot of the dialog where it can't find your email?
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Diane Poremsky
M365 MVP, specializing in Outlook, Exchange, and Microsoft 365 apps.

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Can't get screen shot to work.  Can't copy and paste, either.  Clicked on Sign Into Outlook and got a screen that shows my e-mail, *** Email address is removed for privacy ***, but says "You can't sign in here with a personal account.  Use your work or school account."  I don't have a work or school account.  Can't find any way around this page.

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So you are using Outlook.com on the web. Are you singing into Outlook.live.com or outlook.office365.com? You need to use outlook.live.com for personal accounts.
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Diane Poremsky
M365 MVP, specializing in Outlook, Exchange, and Microsoft 365 apps.

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Okay, now I'm really baffled.  Upon opening Chrome, I've been typing in "Outlook."  That brought up a bunch of links - Log In, 365, Live and others.  I can't remember which I clicked on - I think Log In, but it wasn't 365.  Since I couldn't remember which of those links I've been using, I just tried the usual process - open Chrome, type in "Outlook."  This time, instead of the link choices I've been seeing, there were different links including one to "Mail - charlie henry - outlook - outlook live.com."  That led directly to my e-mail without a fuss.  I've never seen that before.  I just tried it again and got the same results - right to my e-mail.  THAT'S what I've been hoping to achieve.  The address in the Site Information box now reads "Outlook.live.com/mail/0/box."  If I get that result every time I enter "Outlook," I'll be happy.  Can I create a shortcut to this link on my task bar?

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You can't pin it to the task bar using chrome, but can create a shortcut on the Favorites bar in Chrome. You can right click on the taskbar icon and pin the shortcut to the button. Hover over the link and click the pin button.
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Diane Poremsky
M365 MVP, specializing in Outlook, Exchange, and Microsoft 365 apps.

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That worked.  I can access Outlook very easily, now.  Thank you.

Charlie (Car Freak)

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Last updated September 30, 2021 Views 48 Applies to: