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Cannot Send Attachments in Emails with Outlook

Email Send & Receive Issues
Cannot Send Email with Outlook
Cannot Receive Email with Outlook
Cannot Send or Receive Email with Outlook
Cannot Send Attachments in Emails
Retrieve Deleted Emails for Outlook
Problem Description:
Outlook will at times not send attachments with your email messages. This maybe because of certain inbuilt security checks that Outlook performs when sending an email. Certain types of attachments that can be harmful (e.g. program files ending with .exe extension) are automatically blocked. In other scenarios, the emails with attachments will simply sit in the Outbox, and emails without attachment are sent.
Affected Products:
Microsoft Outlook 2013; Microsoft Outlook 2010; Microsoft Outlook 2007; Microsoft Outlook 2003.
Cause of the Problem:
  • Sending attachments types that are blocked automatically by Outlook
  • Sending an attachment that exceeds maximum file size limitation
  • Outlook Personal Folder File (PST file) or Offline Folder File (OST) is corrupted
Instructions for Fixing Email Attachment Problem :
Step 1 : Check Attachment File Type or Extension
  1. To help protect your computer, Microsoft Outlook does not allow you to receive files of certain types (such as .exe files) as attachments, because of their potential for introducing a virus into your computer. Outlook blocks these files by default.
  2. To send a file of a blocked type, you can change the file name extension so that it does not match any of the blocked ones. For example, you can rename program.exe as program.exe_ok, and then attach the file to your e-mail message.
Step 2 : Check Attachment Size
  1. Outlook has default limitations on the size of the attachment you can send. Outlook 2010 for example has a limit of 20 MB.
  2. Check the size of the attachment by Right Clicking on it, and selecting properties. If the size is less than the Outlook limitation, this is not the problem. Go to Step 3.
  3. You have two choices here. First you can send the attachment in smaller chunks. But this may not be always possible.
  4. The other option is to change the default maximum size setting for Outlook. This requires changes to Windows Registry. It is advisable to get help from a qualified technician to change the registry settings.
Step 3 : Scan Outlook PST or OST file
  1. Outlook PST & OST files are proprietary Microsoft databases used to store folders and emails from outlook. When these files get corrupted you may run into problems sending or receiving emails.
  2. Microsoft offers a tool (scanpst.exe) that can repair damaged PST or OST data files. Sometimes this may be the cause of the attachment problem.
  3. This tool will scan the Outlook Data Files (.pst or .ost) stored on your computer and analyzes the file structure integrity. Note if your Outlook files are stored on an Exchange server or you are using a webmail such as Outlook.com, this tool is not of use.
If above steps did not help fix your problem, you need assistance from a certified technician. Please call GuruAid at 1  855  423  6795.