Outlook Not Sending Emails With Attachments - [SOLVED]

Microsoft Outlook is a popular email client that is widely used today for business and personal use. If your Outlook not sending emails with attachments, try these troubleshooting solutions to fix it.

Solution 1: Repair Outlook Profile

  • Step 1: On your Windows computer, launch the Outlook app and click the File tab available at the top-left corner.
  • Step 2: Navigate to the left-side panel and click the Info tab.
  • Step 3: On the right-side pane, click the Account Settings menu and select Account Settings from the drop-down list.
  • Step 4: Choose your account in the pop-up window and click the Repair button.
  • Step 5: In the Repair Account dialog box, verify your account settings and click Next.
  • Step 6: If any changes are required, fill it in the required fields and save them to resolve this Outlook not sending emails with attachments issue.

Solution 2: Run Outlook In Safe Mode

  • Step 1: On your Windows computer, give a right-click on the Start menu and select the Run option from the pop-up menu.
  • Step 2: Type ‘Outlook.exe /safe’ in the Run dialog box and click OK to launch the Outlook app in Safe Mode. Doing so will also disable Add-ins.
  • Step 3: Alternatively, you can launch Outlook in Safe Mode by pressing down the Ctrl key and clicking the Outlook shortcut icon on the desktop.
  • Step 4: If the User Account Control window pops-up, click the Yes button.
  • Step 5: If the Outlook works fine in Safe mode, disable Add-ins.

Solution 3: Increase Outlook Attachment Size

  • Step 1: Launch the Registry Editor window on your Windows computer.
  • Step 2: Make sure no programs are running currently except Windows Registry Editor.
  • Step 3: In the Registry Editor window, navigate to the ‘HKEY_CURRENT_USER\­Software\­Microsoft\­Office\­16.0\­Outlook\­Preferences’ file path.
  • Step 4: Right-click the Maximum Attachment Size entry from the displayed list and create a new DWORD.
  • Step 5: Double-click the created D-WORD and set the value to 25600 in the Value data field.
  • Step 6: Exit from the Registry Editor window and reboot your Windows computer (if necessary).
  • Step 7: Launch the Outlook app and send a test email with attachment to check if the Outlook not sending emails with attachments problem has been resolved.