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When I try to attach a file to a email I get " Ouch?there's a problem attaching

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This seems to be a very common problem, you can try three things -

1, Switch to Classic Mail view
2, Compose a new message and attach the file first before typing anything in the subject line or the body of the email.
3, Upgrade to Internet Explorer 8

Posted on Jul 29, 2010


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Why do I get error messages while I am trying to attach a document to my email on the gmail account? can anyone out there help me with this problem

If you are getting an error message when you are trying to attach a document file to the mails on the gmail, then there can be one of the many reason that the error message is prompted in-front of you while trying to attach the document to your email.
You can find all those reasons below
l Invalid or unauthenticated attachments to the email.
l The file size might be too large to be uploaded to the gmail email.
l The format of the file to be uploaded to the mail might not be supporting the system that leads to an error message.
l You might not be attaching the file or the document in the proper way.
l Documents attached to the mail might be more in number to the available limits of the mail attachments.
l The internet connection from which you are connected might be very slow that might not be allowing you to attach the file to the mail.
The above given are the various reasons of not being able to attach you document or the file to the email you are needing to send. If you have checked above mentioned things and you are still not able to attach a document to mail then visit here
Welcome to Helpline Number USA

May 14, 2018 | Computers & Internet

1 Answer

Brother HL-2280DW scanner won't attach to an email

If you are attempting to attach the file as a .jpg or the like (an image file), it is likely just too large for your email client. Try backing the resolution of the image wayyyy down, it should "bite" and attach if it isn't so large a file.

Jul 20, 2014 | Brother HL Office Equipment & Supplies

1 Answer

Can't get most of my attachments to appear

With the Web-based Yahoo! Mail service, you can attach to your email message a saved Web page or another document in HyperText Markup Language format.
When you attach an HTML file in this way, Yahoo! Mail won't display the HTML content of the attached file in the email message body.
To view the attachment, you must click the attachment tab above the email message.Yahoo! Mail and HTML
Yahoo! Mail is a Web-based service and it's fully compatible with the coding languages used to design and display Web content, including HTML and XML, Extensible Markup Language.
This means emails sent or received in Rich text or HTML format include clickable hyperlinks, graphics and other Web design elements.
However, Yahoo! handles emails with HTML attachments in a different way to email messages formatted with HTML.

About Yahoo! Mail Attachments
Like most email programs and online services, Yahoo! Mail offers an attachment feature for adding images, video clips, audio files and HTML document to email messages.
Some email programs display the content of the attached file in the email message body, but Yahoo! Mail doesn't provide this feature for any file attachment, whether it's an image, video clip or HTML document.

Viewing Yahoo! Mail Attachments When you attach an HTML document or another file to your Yahoo! Mail message, an "Attachments" button labeled with a "Paperclip" icon appears below the email address fields and above the email message body.
Clicking the "Attachments" button opens a pane containing a list of all files attached to the email. The email sender or recipient can open each attachment to view the files by clicking the file name.


When sending a Yahoo! Mail with an attachment, always explain the content of the attachment in the main body of the email message.
A brief explanation will encourage the recipient to click and open the attachment to view the HTML document.
Bear in mind that many email services automatically block HTML attachments because of the security risk of opening HTML files, which can contain viruses, phishing scams or open Web pages with inappropriate content.
If you want to share a favorite Web page with a friend or contact, include a hyperlink to the Web page rather than a saved copy as an HTML attachment.

Oct 17, 2013 | Yahoo Mail

1 Answer

Scanned files fail to attach to emails, it says attachment failed every time.

okay, let me try this again. Scan the documents to a file on your computer and save them, then attach them to your email. it's possible either the email program/provider does not allow the attachment type you're trying to send. it's also possible that the file you're trying to send is too large. normally it will tell you if it's too large though. i'd try to scan the file to pdf and send it that way.

If you need further help, reach me via phone at

May 09, 2012 | Acer Computers & Internet

1 Answer

I could not attach any files to my emails .

- Perhaps they are to large.
Try splitting the attachment into chunks of around 9MB, most web mail services allow around 10MB for a single file attachment.
- Some mail providers may not allow you to attach files with a .exe extension.
In this case compress the attachment in a .zip file.

Feb 27, 2011 | Yahoo Computers & Internet

1 Answer

Info retrns with" ouch , there is a problem with your pdf file" when I try to attach it to outgoing e-mail

If you can't do it directly then you can solve it indirectly ; )..

  1. Firstly confirm your pdf file have no any problem..
  2. After confirm, archive your pdf file to zip format.
  3. attach it to yahoo.

How to archive??
You can archive your file using winrar, zip extractor. and other many more. To download winrar follow this link

Oct 09, 2010 | Yahoo Mail

1 Answer

I keep getting these messages when i try to email something can you help me? 1 File(s) can't be sent | Ouch?there's a problem attaching Questions.doc. (22KB)

You might try to change the file name. Most email systems struggle with any kind of punctuation in a file name. Please check the file name which is denied to sent. ( If this solutions helpful to you please rate it)

Feb 26, 2010 | Yahoo Mail

2 Answers

I cant attach any files to my yahoo emails

Switch back to yahoo mail classic through your options at the top of your mail account page found at the top right.

Dec 17, 2009 | Yahoo Mail

2 Answers

Yahoo email has trouble attaching files...

Please check your Firewall Settings

Jun 24, 2009 | Yahoo Mail

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