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Why is Outlook not allowing me to attach files?

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Why is Outlook not allowing me to attach files?

I can imagine that awkward feeling of you typing an email for your family vacation to Four Seasons Resort Dubai and the only hassle left is at the point of attaching a document as required of them or you just completed tuition for your ward and at the point of sending the proof of payment suddenly becomes a hurdle. Tough one!

Microsoft Outlook by default keeps you connected and secure, combining your email, calendar, and files with the easy use of the application. This implies that all you ever needed had been provided by the application which includes file attachment. This leaves us with just one question: what could you be doing wrongly?

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Often, we are quick to blame an application for not working or serving a purpose it was designed to handle when we are unable to have a grip on what operation we utilize. Most times than none it has been discovered that this happens when we are time-bound, distracted, or perhaps not acquainted with the application. Don’t feel strange; I've been there at some point. 

How about I guide you on possible things you could have missed out on that caused the hitch?


Many people face the problem of being unable to attach a file via Outlook at times. Maybe it doesn't matter if you think you're having this problem in Outlook.com or the desktop app; what I do know is that there are some things or rules that you must follow to send a file via Outlook. Well, there are times when you need to send something urgently and want to avoid the general regulations. I'm sure these tricks will come in handy in such situations.

5 Reasons you are unable to attach files to email in Outlook.com or Microsoft Outlook app

  1. You may need to update or change your browser.
  2. You may need to verify the file size.
  3. You may need to compress in a ZIP file.
  4. You could consider changing your sharing preferences.
  5. You may need to check your Internet connection.

Update or change your browser

Chances are you could be using an outdated version of the browser; it is recommended you update it to the latest version. If that doesn’t provide a positive result, I would suggest you change it. At times it could be the browser extension or security plugin that had blocked the upload process.

Verify file size

Please be reminded that the limit to file size is usually dependent on the email provider, and almost all of them have one thing in common – limited attachment size. It is, therefore, better to confirm the file size before trying to add or upload it, to avoid delay and less anxiety. Often, if the file size is the case, a pop-up would be seen stating: The attachment size exceeds the allowable limit. It is advised that you review the size.

Compress attachment in a ZIP file

Outlook also blocks users from sending some type of files suspected to contain suspicious extensions. This usually happens due to users’ security concerns, since some people often get issues by just downloading the attachment to their computers. However, if you are sending a valid file, but Outlook is blocking you from doing that, apart from having a barrier on the file size, there is only one solution, which is to compress the attachment as a .zip file. Once this is sorted, you can proceed to send it to anyone.

Change Sharing Preference

If you are unable to attach files in Outlook, you could try changing the sharing preferences and seeing if that solves the problem. The Sharing preference is usually set to “Ask me how I want to share them every time”. You could proceed to change it to “Always share them as OneDrive links” or “Always share them as copies”

To have this changed, simply open the Settings panel and then Mail > Attachments.

Check your Internet

I know you could almost vouch for your Internet connection; however, I kindly ask that you check if your connection icon is still up. Check modem, check your CAT5 cable where necessary, check if the signal strength at the point is low, if low you may need to wait before a reattempt. 

These are 5 reasons Outlook will not allow you to attach files. 

For more tips on how to use Outlook, Website Development, Digital Marketing, and SEO, you can always trust The Watchtower, the best and award-winning Website Development Company, Dubai 

  May 12, 2021     by Oluwafemi Smith     204 Views     0

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© Copyright The Watchtower 2010 - .