I can still receive and download attachments. However, when I click on the Insert drop down to attach files to my own emails, I get this message: "We're still getting set up. Please try again." How do I correct this? I'm on a Mac.

Outlook.com has just started refusing to attach files to my e-mail. When I select 'attach file' Outlook crashes.

 

I note advice to select 'options/write e-mails/attachments/always send files as attachments' but there is no option to 'Always send files as attachments' in my 'options' menu', only the 'check for attachments' yes/no option.

 

What has changed and how do I fix this problem. Currently my only option is to reply using my G-mail account where there are no problems with attachments to e-mails.

 

I am using Outlook.com with Windows XP SP3.

 

Come on Microsoft, you shouldn't allow these basic e-mail problems to occur!

 

Chris Jones

When I try to send an attachment in Outlook I get a message that IE has stopped working.  It only happens to me, other users on my laptop who log on and even use my Outlook can send attachments without a problem.  I am the administrator and I cannot send attachments!!  Very frustrating.  Any help would be greatly appreciated.

 

Thanks CBAA 

I lost the ability to use my Skydrive to upload and send large file (JPEGS) attachments in my email after upgrading to 8.1. Previously, I was automatically given the choice of performing this task in my email. I have Office and use Outlook. What gives? Grandma is developing withdrawal symptoms.
using desktop with windows seven and ie10 every time try to attach files get message internet explorer has stopped working and closed and reopened tab even after deleting cookies as suggested   can't send attachments even to self as a self check to see if problem still exists.  have no issues with laptop sending attachments

What's wrong?  I have started using FireFox Browser now since it allows attachments rather than Internet Explorer.

 

How do I fix?

A forum I belong to requires that messages be sent in plain text - with no encoding or attachments.  I have the font set to courier new, have no attachments and have typed URL's in so that they are not active links.  I'm still told that forum administrator that my message was sent:

"in a non-plain-text format.  The most likely cause is that your mail program appended an encoded (HTML - web page formatting) version of your message."

How can I send a message from Outlook.com using a plain text format only?
 I attached a PDF file to an Email, but after I sent the Email the PDF file icon changed to a Microsoft Word icon. This as only just happened because I have sent many similar files in the past successfully. I think I may have somehow inadvertently altered a setting with regard to sending file attachments, but I don't know what or how. Any help would be appreciated. 
On my previous computer (Windows Vista) I was able to copy or drag and drop e-mails and/or attachments from Outlook into my Document folders. I cannot seem to do this with Windows 8.1. Is anyone able to solve this problem?
Hello,
I received an email in my Hotmail account with attachments in Dec 2010.  I have the email address of the person who sent it to me, and the exact date time.  I need the attachments because I am in current litigation with the sender and these documents are important.  How do I ask Microsoft to resend these to me?  Thank you.